Name: 14609-54-2|4,4,4,4-(Porphine-5,10,15,20-tetrayl)tetrakis(benzoic acid)|97%
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SKU: A114047
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1
[ 67-56-1 ]
[ 14609-54-2 ]
[ 22112-83-0 ]

Yield	Reaction Conditions	Operation in experiment
	at 169.84℃; for 168h;Autoclave; High pressure;	Compound 2 wassynthesized by loading TCPP (0.1 mmol, 79.0 mg) and 15 mL methanol into a25 mL Teflon-lined stainless steel autoclave and heating the autoclave at 443 Kfor 7 days. After cooling slowly the mixture to room temperature at 6 K/h, redcrystals suitable for X-ray analysis were collected.

Reference： [1]Magnetic Resonance in Chemistry,1990,vol. 28,p. 1051 - 1057
[2]Journal of the Chilean Chemical Society,2017,vol. 62,p. 3381 - 3385

2
[ 14609-54-2 ]
[ 623-25-6 ]
[ 139328-06-6 ]

Yield	Reaction Conditions	Operation in experiment
69%	With triethylamine In N,N-dimethyl-formamide at 80℃; for 72h;

Reference： [1]Kamogawa, Hiroyoshi; Koga, Kazuhi [Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 1, p. 301 - 303]

3
[ 14609-54-2 ]
4,4',4'',4'''-(21H,23H-porphine-5,10,15,20-tetrayl) tetrakis(benzoic acid chloride) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With oxalyl dichloride In dichloromethane for 1h;
87%	With thionyl chloride for 10h; Heating;
	With thionyl chloride for 2h; Heating;

	With pyridine; thionyl chloride for 4h; Heating;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
	With thionyl chloride for 3.5h; Heating;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃;
	With thionyl chloride
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 16h;
	With oxalyl dichloride; N,N-dimethyl-formamide In chloroform Inert atmosphere; Darkness;
	With pyridine; thionyl chloride In toluene for 3h; Reflux; Inert atmosphere;
	With thionyl chloride Reflux; Inert atmosphere;
	With chlorinating agent Inert atmosphere;
	With thionyl chloride In tetrahydrofuran at 70℃; for 2h;
	With thionyl chloride In 1,2-dichloro-ethane at 8℃; Reflux; Inert atmosphere;	5,10,15,20-tetra(4-(N-stearyl-carboxamide)phenyl)porphyrin (4NC18-TPP) A mixture of TCPP(0.1g, 0.126mmol), SOCl2(5ml) and CH2ClCH2Cl(30ml) were refluxed for 8h under nitrogen atmosphere in a 100ml three-necked flask. The excess SOCl2 and solvent were removed under reduced pressure after the reaction wasfinished. The remanent solid was dissolved in CH2Cl2(40ml) and triethylamine(2ml)and then n-octadecanamine was added into the flask. The mixture was stirred in icewater for 3h and then at room temperature for 12h under the nitrogen protection. Thesolvent was removed and the residue was purified by silica gel columnchromatography using CHCl3 as eluent. The first band was collected and condensedto obtain the target product 4NC18-TPP (79.50mg, 35%).TOF-MS: 1796.245, calcd. for C120H178N8O4 : 1796.400; 1H NMR(400MHz, CDCl3,TMS), δ(ppm) = -2.81(s, 2H, pyrrloe NH), 0.85-0.88(t, 12H, -CH3), 1.25-1.54(m,128H, alkyl CH2 ), 3.63-3.65(t, 8H, -NH-CH2*-), 6.40-6.43(t, 4H, -CO-NH-),8.14-8.28(d, 16H, -C6H4), 8.81(s, 8H, pyrrole ring). IR(KBr), υ (cm-1) = 3306(ν amideN-H and pyrrole N-H), 2918, 2850(ν C-H), 1636(ν C=O), 1539(β, amide N-H), 966(β,pyrrole N-H).
	With thionyl chloride In dichloromethane at 20℃; for 2h;	1 In the first step, the carboxylic acid porphyrin was dissolved in anhydrous methylene chloride,A constant pressure funnel was charged with thionyl chloride,The reaction was stirred at room temperature for 2 hours. In the second step, triethylamine was added to the solution and then pentylamine (NH2C5Hn) was added and the reaction was carried out at a temperature of -8 ° C20 hours.Removal of solvent gaveN, N ', N', N ' -Pentyl-4, 4 ', 4', 4 '? - (5,10,15,20-tetraphenylporphyrin)Tetraamide(TPP-TNC5).The purified amide-type porphyrin derivative was separated by a column. The rinsing solution was a mixed solvent of dichloromethane and methanol, and the volume ratio was 7: 1.
	With thionyl chloride In tetrahydrofuran at 65℃; for 2h; Inert atmosphere;
	With thionyl chloride

Reference： [1]Choi, Myung-Seok; Aida, Takuzo; Yamazaki, Tomoko; Yamazaki, Iwao [Chemistry - A European Journal, 2002, vol. 8, # 12, p. 2667 - 2678]
[2]Suarez, Margarita; Salfran, Esperanza; Curiel, Rene I. Rodriguesz; Elguero, Jose [Bulletin des Societes Chimiques Belges, 1997, vol. 106, # 4, p. 211 - 214]
[3]Schneider, Hans-Joerg; Wang, Manxue [Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7473 - 7478]
[4]Gauuan, Polivina Jolicia F; Trova, Michael P; Gregor-Boros, Livia; Bocckino, Stephen B; Crapo, James D; Day, Brian J [Bioorganic and medicinal chemistry, 2002, vol. 10, # 9, p. 3013 - 3021]
[5]Wilson, Andrew J.; Groves, Kevin; Jain, Rishi K.; Park, Hyung Soon; Hamilton, Andrew D. [Journal of the American Chemical Society, 2003, vol. 125, # 15, p. 4420 - 4421] Gradl, Stefan N.; Felix, John P.; Isacoff, Ehud Y.; Garcia, Maria L.; Trauner, Dirk [Journal of the American Chemical Society, 2003, vol. 125, # 42, p. 12668 - 12669] Groves, Kevin; Wilson, Andrew J.; Hamilton, Andrew D. [Journal of the American Chemical Society, 2004, vol. 126, # 40, p. 12833 - 12842]
[6]Králová, Jarmila; Dvořák, Michal; Král, Vladimír [Journal of Medicinal Chemistry, 2003, vol. 46, # 11, p. 2049 - 2056]
[7]Beil, James B.; Zimmerman, Steven C. [Macromolecules, 2004, vol. 37, # 3, p. 778 - 787]
[8]Kawano, Shin-Ichiro; Tamaru, Shun-Ichi; Fujita, Norifumi; Shinkai, Seiji [Chemistry - A European Journal, 2004, vol. 10, # 2, p. 343 - 351]
[9]Jain, Rishi K.; Hamilton, Andrew D. [Organic Letters, 2000, vol. 2, # 12, p. 1721 - 1723]
[10]Rajesh, Cheruvallil S.; Capitosti, Gregory J.; Cramer, Susan J.; Modarelli, David A. [Journal of Physical Chemistry B, 2001, vol. 105, # 42, p. 10175 - 10188]
[11]Fletcher, Steven; Hamilton, Andrew D. [New Journal of Chemistry, 2007, vol. 31, # 5, p. 623 - 627]
[12]Helmich, Floris; Lee, Cameron C.; Schenning, Albertus P. H. J.; Meijer [Journal of the American Chemical Society, 2010, vol. 132, # 47, p. 16753 - 16755]
[13]Location in patent: experimental part Maligaspe; Kumpulainen; Subbaiyan; Zandler; Lemmetyinen; Tkachenko; D'Souza [Physical Chemistry Chemical Physics, 2010, vol. 12, # 27, p. 7434 - 7444]
[14]Location in patent: experimental part Chen, Yuting; Jiang, Jianzhuang [Organic and Biomolecular Chemistry, 2012, vol. 10, # 24, p. 4782 - 4787]
[15]Presolski, Stanislav I.; Van Der Weegen, Rob; Wiesfeld, Jan J.; Meijer [Organic Letters, 2014, vol. 16, # 7, p. 1864 - 1867]
[16]Ghafuri, Hossein; Movahedinia, Zahra; Rahimi, Rahmatollah; Esmaili Zand, Hamid Reza [RSC Advances, 2015, vol. 5, # 74, p. 60172 - 60178]
[17]Zhang, Xiaoyuan; Zhu, Biaobiao; Zhou, Li; Liu, Ping; Deng, Wenji [Synthetic Communications, 2015, vol. 45, # 23, p. 2730 - 2739]
[18]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN103374004, 2016, B Location in patent: Paragraph 0017-0019
[19]Dasgupta, Jyotishman; Kundu, Arup; Maji, Tapas Kumar; Rahimi, Faruk Ahamed; Samanta, Debabrata; Verma, Parul [Angewandte Chemie - International Edition, 2022, vol. 61, # 16][Angew. Chem., 2022, vol. 134, # 16]
[20]Zhang, Xu-Jie; Morishita, Daiki; Aoki, Tsubasa; Itoh, Yoshimitsu; Yano, Keiichi; Araoka, Fumito; Aida, Takuzo [Chemistry - An Asian Journal, 2022, vol. 17, # 10]

4
[ 109-97-7 ]
[ 619-66-9 ]
[ 14609-54-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: pyrrole; 4-formylbenzoic acid In N,N-dimethyl-formamide at 100℃; for 0.166667h; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 150℃; for 1h; Inert atmosphere;	General procedures for the synthesis of porphyrins 1-5 General procedure: General procedures for the synthesis of porphyrins 1-5A mixture of the appropriate aromatic aldehyde (0.72 mmol) andpyrrole (0.72 mmol) in DMF (15 mL) was placed into a 50 mL threeneckedflask. The mixture was flushed with nitrogen gas for a coupleof minutes and then heated to 100 C for 10 min. P-toluene sulphonicacid (0.72 mmol, dissolved in DMF) was then added to the reactionmixture. The colorless mixture turned red over the next couple of minutesthen heated at 150 C for 1 h. The reaction mixture was thencooled and poured over ice with stirring for 15 min the residue wascollected, dried under vacuum and purified by column chromatographyusing chloroform/hexane (1.5/1) as eluent).
55%	In propionic acid for 2h; Reflux;
55%	With propionic acid at 20℃; for 2h; Reflux;

55%	With propionic acid for 2h; Reflux;
55%	With glacial acetic acid for 2h; Reflux; Inert atmosphere; Schlenk technique;
51%	Stage #1: 4-formylbenzoic acid With propionic acid at 80℃; Stage #2: pyrrole for 2h; Reflux;
50%	In propionic acid for 2h; Reflux;
50%	With propionic acid at 70℃; for 4h;
42.2%	With propionic acid at 140℃; for 1.5h;	2.2. Synthesis of H6TCPP The ligand tetrakis (4-carboxyphenyl)-porphyrin (H6TCPP) was synthesizedbased on the reported procedures [45]with some modificationsso that the product can be obtained without using column chromatography.Pyrrole was distilled before use. 4-carboxybenzaldehyde (4.5 g,0.030 mol) was dissolved in propionic acid (200 mL) at 120 C in a 500mL round flask, into which pyrrole (2.07 mL, 0.0298 mol) was slowlyadded over 40-60 min under stirring. The temperature was then raised to140 C and the mixture was stirred for 1.5 h. The mixture was then cooledto room temperature, and transferred into a 1000 mL flask. 200 mL ofmethanol was used to help the transfer. Then the mixture was put intorefrigerator (10 C) for 12 h. The deep-purple crystals appeared. Themixture was filtered and washed three times with hot water (80 C, 200mL) using Büchner funnel. The precipitate was then washed withmethanol (The amount is just enough to immerse the precipitate), andfiltered using Büchner funnel. The obtained solid was dried at 100 Cuntil the weight became constant (12-18 h). The solid was put into adesiccator when still hot and cooled and stored in the desiccator. 2.51 g(0.00317 mol) of H6TCPP was obtained with 42.2% of yield. The productswere pure enough to be used in making PMOFs. 1H NMR spectra ofvarious products were given in Fig. S5. Some of the products containssmall amounts of propionic acids. To remove the propionic acids, moremethanol can be used in the final washing stage.
33.91%	In propionic acid at 20℃; for 10h;	5,10,15,20-Tetrakis(4-carboxyphenyl)porphyrin(TCPP) Pyrrole (8 mmol) and 4-carboxybenzaldehyde(8 mmol) were mixed in propionic acid (100 mL); the mixturewas left under stirring for 10 h at room temperatureopen to the atmosphere. The product (corresponding to theTCPP) porphyrin was obtained by the addition of cool methanol(80 mL) to the obtained mixture. Afterward, the TCPPwas purified by means of a column chromatography usingalumina as stationary phase and petroleum ether:ethyl acetate2:1 as mobile phase. The product showed an rf = 0.80.Yield 0.7596 g (33.91%); melting point > 300 °C; UV-Vis(ethyl acetate) λ (nm): 416, 513, 548, 590, 644; FT-IR-ART
32%	With propionic acid at 140℃; for 1h;	Synthesis of meso-tetra (4-carboxyphenyl)porphyrin (TCPP) Meso-tetra (4-carboxyphenyl) porphyrin (TCPP) was preparedby the modification Adler et al. [34]. 10 mmol (1.5 g)from 4-carboxybenzaldehyde, 10 mmol (0.67 g) from freshlydistilled pyrrole and 100 mL of propionic acid were pouredinto a 250-mL round-bottomed flask. Then, the mixturewas stirred at 140 °C for 60 min. Afterward, the solutionwas placed at room temperature to precipitate formed. Thedark purple product was filtrated then purified by ethanol.A favorable purple solid of tetrakis (4-carboxyphenyl) porphyrinwas obtained (efficiency: 32%)
30%	With propionic acid at 100℃; for 12h; Darkness;
25.1%	In propionic acid for 2h; Reflux;
19%	With propionic acid for 0.5h; Heating;
18%	With propionic acid for 4h; Reflux; Schlenk technique;
16%	With propionic acid for 1.5h; Heating;
16%	With propionic acid for 1.5h; Reflux;
12%	With propionic acid for 2h; Schlenk technique; Reflux;
12%	In propionic acid for 2h; Reflux; Inert atmosphere;	2.1. Synthesis of copper- meso -tetrakis-(4-carboxyphenyl)porphyrin (Cu-TCPP) The synthesis of ligand meso -tetrakis-(4-carboxyphenyl)- porphyrin (TCPP) was achieved by taking terephthaladehydic acid (0.338 g, 2.25 mmol) and dried pyrrole (0.2 mL, 0.193 g, 2.88 mmol) in two neck round bottom flask containing propionic acid (100 mL). The reaction mixture was refluxed in inert atmosphere (N 2 atmosphere) for two hours. After the completion of the reaction, the mixture was cooled to room temperature and the precipitated product was filtered, washed with cold methanol and dried. Subsequently, the product was recrystallized in 1:1 chloroform-acetone mixture and purple coloured crystals were obtained (12% yield). For the preparation of copper- meso -tetrakis- (4-carboxyphenyl)porphyrin (Cu-TCPP) complex, metal salt cupric chloride was dissolved in 5 mL of dry methanol. Dropwise addition of the dissolved salt was then carried out in to the round bottom flask containing solution of 1 mmol of TCPP in dry acetone (45 mL) under nitrogen atmosphere. The final reaction mixture was refluxed for 24 h under N 2 atmosphere. After reaction comple- tion, the solvent was evaporated and impurities were removed by washing the crude product with methanol and acetone. Finally, the dark green coloured solid product was isolated, (Yield: 86%).
10.5%	In propyl alcohol
10%	With propionic acid for 1.5h; Reflux;
	In propionic acid	1.A A. 1.50 g 4-Carboxy-benzaldehyde (0.01 mole) and 0.69 mL pyrrole (0.01 mole) were combined in 150 mL propionic acid. The mixture was refluxed for 2 to 4 hours, cooled to room temperature, and then filtered through a fine frit. The resulting solid was then extracted into methanol and filtered through a medium frit. The filtrate was placed in a round-bottom flask, and the methanol removed on a rotary evaporator, leaving a solid purple residue. The recovered solid was then dried overnight under vacuum. Yield: 0.83 g.; 42%.
	With propionic acid for 2h; Reflux;
	With propionic acid In nitrobenzene at 120℃; for 1h;
	With propionic acid In nitrobenzene at 120℃; for 1h;
	With propionic acid at 120℃; for 4h;
	In propionic acid at 90 - 141℃; for 3h;
	With propionic acid In nitrobenzene at 120℃; for 1h;	2.3 Synthesis of porphyrin The carboxyphenylporphyrin (TCPP) was synthesized according to methods described in the literature [30,31]. Pyrrole (30mmol) was added to a mixture of 4-carboxybenzaldehyde (30mmol), propionic acid (105mL) and nitrobenzene (45mL). The mixture was heated 1h at 120°C. After cooling and solvent removal under vacuum, the porphyrin was dissolved in 250mL of 0.1M NaOH. The porphyrin was then precipitated with 1M HCl solution, dissolved in ethanol and recrystallized by solvent evaporation. FT-IR (KBr, cm-1): 1605s [C=C]; 1110s, 1006s, 1307m, 1311m, 1531m, 1485m [pyrrole ring]; 1699s [C=O]; 1404m, 1268s [C-O] [32].
	Stage #1: pyrrole; 4-formylbenzoic acid With glacial acetic acid at 120℃; for 0.5h; Stage #2: With pyridine for 1h;
	With propionic acid In nitrobenzene at 120℃; for 1h;	2.2.1 Synthesis of TCPP The TCPP was synthesized according to the methods already described in the literature [17]. Pyrrole (30mmol) was added to a mixture of 4-carboxybenzaldehyde (30mmol), propionic acid (105mL) and nitrobenzene (45mL). The mixture was heated for 1h at 120°C; afterward, the solvent was removed under vacuum. Then, the porphyrin was dissolved in 250mL of 0.100M NaOH and was precipitated with a 1.0M HCl solution. Finally, it was dissolved in ethanol and recrystallized in a rotary evaporation system.
	In propionic acid for 1h; Reflux; Darkness;
	With propionic acid at 120 - 140℃;	2.1.1 General Procedure of the Synthesis of Porphyrins General procedure: Porphyrins were prepared using the typical Adler reaction. Pyrrole (30 mmol) was slowly added to a mixture of substituted benzaldehyde (30 mmol) and propionic acid (105 mL) through a dropping funnel. The mixture was heated to 120-140 °C for 1-3 h. After cooling, the reaction mixture was filtered, washed and dried under vacuum to obtain the crystal of porphyrins.
	With propionic acid In nitrobenzene for 2h; Reflux;
	In propionic acid for 2h; Reflux;
	With propionic acid Reflux;	General procedure for the preparation of porphine and metalloporphine H2TCPP was prepared by refluxing 4-carboxybenzaldehyde (300mg, 2mmol) and pyrrole (0.12mL, 1.8mmol) in propionic acid as described by Adler et al. [33] and then, Mn(TCPP)OAc was prepared according to the literature [34].
	Acidic conditions;
	With propionic acid In nitrobenzene at 120℃; for 1h;	2.2.1. Synthesis of TCPP The TCPP was synthesized according to the methods alreadydescribed in the literature [17]. Pyrrole (30 mmol) was added to a mixture of 4-carboxybenzaldehyde (30 mmol), propionic acid(105 mL) and nitrobenzene (45 mL). The mixture was heated for1 h at 120 °C; afterward, the solvent was removed under vacuum.Then, the porphyrin was dissolved in 250 mL of 0.100 M NaOH andwas precipitated with a 1.0 M HCl solution. Finally, it was dissolvedin ethanol and recrystallized in a rotary evaporation system
	With propionic acid for 12h; Reflux;
	With propionic acid for 1h; Reflux;
	In propionic acid Reflux;
	In propionic acid Reflux;	3.1. Synthesis General procedure: Meso-tetrakis(4-carboxyphenyl) porphyrin (TCPP) andmeso-tetrakis(4-dimethyl amino) porphyrin(TDAP)were synthesized using the Adler-Longomethod [27] bymixing pyrrolewith 4-formyl benzoic acidand 4-dimethyl amino benzaldehyde, respectively, in propionic acid under reflux conditions. TCPP waspurified by chromatography with chloroformandmethanol. TDAP was first washed with coldmethanoland later purified with chloroformby chromatography.
	In propionic acid at 145℃; for 2h; Inert atmosphere; Darkness;	General procedure: In the typical procedureof porphyrin syntheses, benzaldehyde or its derivatives(150mmol) was heated to refluxing (145 °C) with stirring in propionic acid (450mL) under the nitrogen protection,followed by the addition of redistilled pyrrole (150mmol)dropwise under refluxing conditions. After refluxing for2.0h in the shield from ambient light, the resultant mixturewas cooled in air to room temperature and kept standinguntil a large amount of solid appeared. Then the solid wascollected through suction filtration and suspended in methanol(200mL) with stirring for 6.0h. The collected purplishred precipitate was washed successively using methanol(2 × 100mL) and purified through silica column chromatographyseparation with cyclohexane and dichloromethaneas eluent (10:1-4:1, volume/volume).
	With propionic acid Reflux;
	With propionic acid at 140℃; for 2h;	2.2.1. Synthesis of TCPP According to the previous report, a metal-free tetrakis (4-carboxyphenyl)porphyrin (TCPP) was synthesized with a slight modification[23]. Briefly, 20.25 mmol (3.04 g) of 4-formylbenzoic acid and 20.25mmol (1.4g) of pyrrole were put into a 250 mL round-bottom flaskrespectively, then 75 mL of propionic acid was added into the flask. Themixture was heated to 140 °C and refluxed for 2 h. After cooling down toroom temperature, the obtained black mixture was diluted with 80 mL ofmethanol and stirred for 0.5 h in an ice water bath. Subsequently, thefinal mixture was centrifuged and washed with methanol and warmwater for several times until the liquid became clear. Finally, the solidproduct was dried in a vacuum oven at 80 °C for 12 h.
	Stage #1: 4-formylbenzoic acid In propionic acid for 0.0833333h; Reflux; Stage #2: pyrrole In propionic acid for 1h; Reflux;	Synthesis General procedure: Tetraphenyl porphyrin (TPP) was synthesized similarly to previous reports ADDIN EN.CITE Adler1967171171717Adler, Alan D.Longo, Frederick R.Finarelli, John D.Goldmacher, JoelAssour, JacquesKorsakoff, LeonardA simplified synthesis for meso-tetraphenylporphineThe Journal of Organic ChemistryThe Journal of Organic Chemistry476-47632219671967/02/01American Chemical Society0022-3263https://doi.org/10.1021/jo01288a05310.1021/jo01288a0531. Briefly, TPP was generated by direct condensation of pyrrole and benzaldehyde. 0.5 mL benzaldehyde was refluxed in 10 mL propionic acid. Over the period of 5 minutes, pyrrole (375 mg) in propionic acid (10 mL) was added dropwise. The reaction continued to reflux for 1 hour. After, the reaction was allowed to slowly cool to room temperature. The product was filtered via vacuum filtration and washed with a small amount of cold acetone to yield a deep purple crystalline product.
	With propionic acid Reflux;

Reference： [1]Abou-Zeid, Laila; Ahmed, Asmaa; El-Asmy, Hala A.; Fadda, Ahmed A.; Omar, Walaa A. E. [Dyes and Pigments, 2020, vol. 183]
[2]Daly; Al-Sabi; Kinsella; Nolan; Dolly [Chemical Communications, 2015, vol. 51, # 6, p. 1066 - 1069]
[3]Das, Subhendu K.; Ghosh, Arijit; Paul Chowdhuri, Srijita; Halder, Nyancy; Rehman, Ishita; Sengupta, Souvik; Sahoo, Krushna Chandra; Rath, Harapriya; Das, Benu Brata [Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 804 - 817]
[4]Chakraborty, Ritobrita; Sahoo, Sumit; Halder, Nyancy; Rath, Harapriya; Chattopadhyay, Krishnananda [ACS Chemical Neuroscience, 2019, vol. 10, # 1, p. 573 - 587] D'yakonov, Vladimir A.; Dzhemilev, Usein M.; Dzhemileva, Lilya U.; Halder, Nyancy; Ramazanov, Ilfir R.; Rath, Harapriya [ChemMedChem, 2020]
[5]De Bruin, Bas; Mathew, Simon; Meeus, Eva J.; Mouarrawis, Valentinos; Reek, Joost [Journal of Porphyrins and Phthalocyanines, 2021]
[6]Cardenal, Ashley D.; Jeong Park, Hye; Chalker, Cody J.; Ortiz, Kacey G.; Powers, David C. [Chemical Communications, 2017, vol. 53, # 53, p. 7377 - 7380]
[7]Li, Linnan; Shen, Sensen; Lin, Ruoyun; Bai, Yu; Liu, Huwei [Chemical Communications, 2017, vol. 53, # 72, p. 9986 - 9989]
[8]Wang, Xiao-Ning; Li, Jiang-Li; Zhao, Yu-Meng; Pang, Jiandong; Li, Bao; Zhang, Tian-Le; Zhou, Hong-Cai [Chemical Communications, 2019, vol. 55, # 46, p. 6527 - 6530]
[9]Bao, Jianchun; Ding, Jie; Fang, Min; Feng, Yuying; Jia, Shuyu; Li, Ke; Wu, Yong; Wu, Yusheng [Journal of Solid State Chemistry, 2020, vol. 292]
[10]Espitia-Almeida, Fabián; Díaz-Uribe, Carlos; Vallejo, William; Peña, Orlando; Gómez-Camargo, Doris; Bohórquez, Arnold R. Romero; Zarate, Ximena; Schott, Eduardo [Chemical Papers, 2021, vol. 75, # 9, p. 4817 - 4829]
[11]Gharehdaghi, Zahra; Rahimi, Rahmatollah; Naghib, Seyed Morteza; Molaabasi, Fatemeh [Journal of the Iranian Chemical Society, 2022, vol. 19, # 7, p. 2727 - 2737]
[12]Fu, Chenchen; Sun, Xinran; Zhang, Guoda; Shi, Pengfei; Cui, Ping [Inorganic Chemistry, 2021, vol. 60, # 2, p. 1116 - 1123]
[13]Wu, Yanyu; Veleta, José M.; Tang, Diya; Price, Alex D.; Botez, Cristian E.; Villagrán, Dino [Dalton Transactions, 2018, vol. 47, # 26, p. 8801 - 8806]
[14]Suarez, Margarita; Salfran, Esperanza; Curiel, Rene I. Rodriguesz; Elguero, Jose [Bulletin des Societes Chimiques Belges, 1997, vol. 106, # 4, p. 211 - 214]
[15]Anjali, Kaiprathu; Aswini, Manammuzhangiyil Sivadasan; Aswin, Peringayi; Ganesh, Venkatachalam; Sakthivel, Ayyamperumal [European Journal of Inorganic Chemistry, 2019, vol. 2019, # 38, p. 4087 - 4094]
[16]Garcia, Guillaume; Sol, Vincent; Lamarche, Francois; Granet, Robert; Guilloton, Michel; Champavier, Yves; Krausz, Pierre [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 12, p. 3188 - 3192]
[17]Location in patent: scheme or table Garcia, Guillaume; Sarrazy, Vincent; Sol, Vincent; Morvan, Caroline Le; Granet, Robert; Alves, Sandra; Krausz, Pierre [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 2, p. 767 - 776]
[18]Anjali, Kaiprathu; Christopher, Jayaraj; Sakthivel, Ayyamperumal; Venkatesha, Naragalu J. [New Journal of Chemistry, 2020, vol. 44, # 26, p. 11064 - 11075]
[19]Anjali, Kaiprathu; Ganesh, Venkatachalam; Christopher, Jayaraj; Sakthivel, Ayyamperumal [Journal of Organometallic Chemistry, 2020, vol. 929]
[20]Ricoux, Remy; Allard, Mathieu; Dubuc, Roger; Dupont, Claude; Marechal, Jean-Didier; Mahy, Jean-Pierre [Organic and Biomolecular Chemistry, 2009, vol. 7, # 16, p. 3208 - 3211]
[21]Adineh, Maryam; Tahay, Pooya; Ameri, Mohsen; Safari, Nasser; Mohajerani, Ezeddin [RSC Advances, 2016, vol. 6, # 18, p. 14512 - 14521]
[22]Current Patent Assignee: BRACCO SPA - US5262532, 1993, A
[23]Location in patent: experimental part Rahimi, Rahmatollah Rahimi; Moharrami, Fariba Moharrami; Rahmanpour, Seyed Hamed Rahmanpour [Asian Journal of Chemistry, 2010, vol. 22, # 6, p. 4398 - 4404]
[24]Location in patent: experimental part Diaz-Uribe, Carlos E.; Daza, Martha C.; Martínez, Fernando; Páez-Mozo, Edgar A.; Guedes, Carmen L.B.; Di Mauro, Eduardo [Journal of Photochemistry and Photobiology A: Chemistry, 2010, vol. 215, # 2-3, p. 172 - 178]
[25]Location in patent: experimental part Granados-Oliveros, Gilma; Páez-Mozo, Edgar Alberto; Martínez Ortega, Fernando; Piccinato, Marileneturini; Silva, Fausto Neves; Guedes, Carmen Luísa Barbosa; Di Mauro, Eduardo; Costa, Marcello Ferreira Da; Ota, André Tsutomu [Journal of Molecular Catalysis A: Chemical, 2011, vol. 339, # 1-2, p. 79 - 85]
[26]Location in patent: experimental part Jeong, Eun-Young; Burri, Abhishek; Lee, Seung-Yeop; Park, Sang-Eon [Journal of Materials Chemistry, 2010, vol. 20, # 48, p. 10869 - 10875]
[27]Location in patent: experimental part Adilina, Indri Badria; Hara, Takayoshi; Ichikuni, Nobuyuki; Shimazu, Shogo [Journal of Molecular Catalysis A: Chemical, 2012, vol. 361-362, p. 72 - 79]
[28]Diaz-Uribe, Carlos E.; Daza, Martha C.; Páez-Mozo, Edgar A.; Martínez O., Fernando; Guedes, Carmen L.B.; Di Mauro, Eduardo [Journal of Photochemistry and Photobiology A: Chemistry, 2013, vol. 259, p. 47 - 52]
[29]Managa, Muthumuni; Antunes, Edith; Nyokong, Tebello [Polyhedron, 2014, vol. 76, p. 94 - 101]
[30]Diaz-Uribe, Carlos E.; Vallejo L., William A.; Miranda, Jarol [Journal of Photochemistry and Photobiology A: Chemistry, 2014, vol. 294, p. 75 - 80]
[31]Jiang, Yue-Xiu; Su, Tong-Ming; Qin, Zu-Zeng; Huang, Guan [RSC Advances, 2015, vol. 5, # 31, p. 24788 - 24794]
[32]Sun, Weizhi; Liu, Yaojie; Zhang, Haibo; Xian, Mo; Liu, Huizhou [Catalysis Letters, 2015, vol. 145, # 11, p. 1991 - 1999]
[33]Safaei, Elham; Mohebbi, Sajjad [Journal of Materials Chemistry A, 2016, vol. 4, # 10, p. 3933 - 3946]
[34]Rhauderwiek, Timo; Waitschat, Steve; Wuttke, Stefan; Reinsch, Helge; Bein, Thomas; Stock, Norbert [Inorganic Chemistry, 2016, vol. 55, # 11, p. 5312 - 5319]
[35]Rayati, Saeed; Sheybanifard, Zahra; Amini, Mostafa M.; Aliakbari, Azam [Journal of Molecular Catalysis A: Chemical, 2016, vol. 423, p. 105 - 113]
[36]Castro, Kelly A.D.F.; Moura, Nuno M.M.; Fernandes, Ana; Faustino, Maria A.F.; Simões, Mário M.Q.; Cavaleiro, José A.S.; Nakagaki, Shirley; Almeida, Adelaide; Cunha, Ângela; Silvestre, Armando J.D.; Freire, Carmem S.R.; Pinto, Ricardo J.B.; Neves, Maria da Graça P.M.S. [Dyes and Pigments, 2017, vol. 137, p. 265 - 276]
[37]Diaz-Uribe, Carlos E.; Vallejo L., William A.; Miranda, Jarol [Journal of Photochemistry and Photobiology A: Chemistry, 2014, vol. 294, p. 75 - 80]
[38]Li, Zhong; Li, Xue; Chen, Chong; Zhou, Lijin; Guo, Qirui; Yuan, Dashui; Wan, Hui; Ding, Jing; Guan, Guofeng [European Journal of Inorganic Chemistry, 2018, vol. 2018, # 2, p. 194 - 202]
[39]Zhang, Wei; Lu, Jun; Gao, Xiaonan; Li, Ping; Zhang, Wen; Ma, Yu; Wang, Hui; Tang, Bo [Angewandte Chemie - International Edition, 2018, vol. 57, # 18, p. 4891 - 4896][Angew. Chem., 2018, vol. 130, # 18, p. 4985 - 4990,6]
[40]Bagherzadeh, Mojtaba; Mesbahi, Elnaz [Applied Organometallic Chemistry, 2019, vol. 33, # 1]
[41]Sánchez-Muñoz, Esteban; Gárate-Morales, José L.; Sandoval-Lira, Jacinto; Hernández-Pérez, Julio M.; Aguilar-Sánchez, Rocío [Molecules, 2019, vol. 24, # 18]
[42]Shen, Hai-Min; Qi, Bei; Hu, Meng-Yun; Liu, Lei; Ye, Hong-Liang; She, Yuan-Bin [Catalysis Letters, 2020, vol. 150, # 11, p. 3096 - 3111]
[43]Vicente-Escobar, Jonathan Osiris; García-Sánchez, Miguel A.; González; Cipagauta-Díaz; Estrella González [Chemical Papers, 2021, vol. 75, # 9, p. 4501 - 4515] Shokoohi, Saeedeh; Rayati, Saeed [Journal of Porphyrins and Phthalocyanines, 2022, vol. 26, # 1, p. 8 - 18]
[44]Guo, JiaQing; Li, JiaMin; Mu, Manman; Shen, Haochen; Wu, Guang; Yin, Xiaohong [Journal of Solid State Chemistry, 2022, vol. 309]
[45]Asadinamin, Mona; Bernot, Anthony R.; Hanna, Lauren; Marshall, Nicholas; Movsesian, Edgar; Orozco, Miguel; Shenje, Learnmore; Teprovich, Joseph A.; Thomas, Michael B.; Ullrich, Susanne; Ward, Patrick A.; Weeks, Jason A.; Zhao, Yiping [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2022, vol. 278]
[46]Zuo, Weiguo; Yang, Shunbin; Xing, Yajie; Xiao, Xiwen; Fan, Duona; Li, Hengyu; Wang, Guanqun; Qin, Bin; You, Song; Jia, Xian [Dalton Transactions, 2022, vol. 51, # 17, p. 6631 - 6637]

5
[ 7524-50-7 ]
[ 14609-54-2 ]
5,10,15,20-tetrakis([N-(1-methoxycarbonyl-2-phenyl)ethyl]-4-carboxamido phenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 18h;
	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 24h;

Reference： [1]Figueiredo, Telmo L. C.; Johnstone, Robert A. W.; SantAna Sorensen, Alexandra M.P.; Burget, Dominique; Jacques, Patrice [Photochemistry and Photobiology, 1999, vol. 69, # 5, p. 517 - 528]
[2]Yang, Xuejiao; Shen, Yuhe; Liu, Jiayu; Wang, Yuefei; Qi, Wei; Su, Rongxin; He, Zhimin [Langmuir, 2021, vol. 37, # 44, p. 13067 - 13074]

6
[ 22112-83-0 ]
[ 14609-54-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium hydroxide; In tetrahydrofuran; water monomer; at 75℃; for 16h;	General procedure: Tetramethylester (0.593 g, 0.70 mmol) or octaethylesterporphyrin (0.834 g, 0.70 mmol) was dissolved in 100 mL THF in atwo neck round bottom flask. To this, 10 mL of aq. solution of KOH(300 equivalents) was added and refluxed for 16 h at 75 C. Aftercompletion of the reaction, THF was removed using rotary evaporatorand the resulting residue was treated with 2N HCl (150 mL)which resulted green precipitate, filtered and washed with water(50 mL x 5). The protonated porphyrin was neutralized with pyridine(15 mL). Then, the pyridine was removed by rotary evaporationand the resulting residue was washed with water (50 mL x 3)and dried under vacuum. The crude porphyrin was recrystallizedfrom CHCl3 and acetone mixture (3:7, v/v). The yield was found tobe 0.54 g (98%) for the corresponding tetraacid and 0.680 g (100%)for octaacid.
96%	With methanol; water monomer; potassium hydroxide; In tetrahydrofuran; for 24h;Reflux;	The prepared TCPPCOOMe (4.2 g) was stirred in a mixed solvent of tetrahydrofuran (80 mL) and methyl alcohol (80 mL),It was added to 80 ml of a KOH aqueous solution (0.24 mol, 13.5 g). after, The mixture was refluxed for 24 hours, then cooled to room temperature.Before evaporating trahydrofuran and methyl alcohol,The mixture was filtered with filter paper (grade 2, 8 μm).Additional water was added to the resulting water phase. The aqueous solution was filtered again with filter paper. after,The solution was acidified to pH 2 with 1M HCl. The precipitate is washed with water,Collected by centrifugation,TCPP was prepared by vacuum drying (Schlenk line) (4.7 mmol, 3.7 g, yield 96%).
89%	With potassium hydroxide; In tetrahydrofuran; for 24h;Reflux;	TCMPP(0.4g, 0.47mmol), KOH solution(20ml, 5% mass ratio) and THF(70ml) wereadded to a 150ml round-bottom flask and refluxed for 24h. The reaction wasmonitored by thin-layer chromatography (TLC). THF was removed through rotaryevaporator after the reaction was finished, and the mixture was carefully neutralizedwith dilute HCl solution to pH = 2-3. Washed the solid with distilled water for severaltimes and obtained TCPP (0.33g, yield 89%).MS (ESI): m/z = 791.5 [M+H]+, calcd. for C48H30N4O8 : 790.7; 1H NMR ( 400 MHz,DMSO, TMS) δ (ppm) = 8.82 (s, 8H, pyrrole ring), 8.25-8.38(d, 16H, -C6H4), -2.90 (s,2H, pyrrloe NH); IR (KBr) υ (cm-1) = 3635, 3315, 1710, 1605, 1475, 1401, 963

88%	With water monomer; potassium hydroxide; In tetrahydrofuran; methanol; at 100℃; for 12h;	The obtained <strong>[22112-83-0]TPPCOOMe</strong> (0.25 g, 2.9mmol) was added in mixed solvent of MeOH (10 mL) andtetrahydrofuran (THF, 10 mL). Then, a solution of KOH (0.49 g, 8.7 mmol, 10 mL)was introduced. After refluxing and stirring for 12 h at 100 C, THF and MeOH in theresulting solution were evaporated. Then, additional water was added to the resultingaqueous phase. The mixture was heated until solids were completely dissolved. Thehomogeneous solution was acidified with 1 mol/L HCl until no further precipitatedetected. The green solid (0.26g, 88%) was collected by filtration, washed with waterand dried in vacuum.1H NMR (400 MHz, DMSO-d6): δ 8.82 (s, 8H), 8.33 (q, J = 8.3Hz, 16H) (Fig. S3). m/z = 790.6 (Fig. S4).
80%	With hydrogenchloride; In trifluoroacetic acid; at 85℃; for 36h;	H2(<strong>[22112-83-0]TMCPP</strong>) (0.12 mmol) was dissolved in 5 ml of trifluoroacetic acid, then 2.5 mL of HCl (35%)was added to the solution, and the mixture was stirred at 85 C for 36 h. The reaction mixturewas diluted with cold water to give green precipitate, filtered, and washed with water andCH2Cl2 at three times to remove unreacted H2(<strong>[22112-83-0]TMCPP</strong>). The green solid was dissolved in 10 mLpyridine, filtered, and evaporated. After washing with water and CH2Cl2 to afford H2(TCPP) in80% yield as purple powder.H2(TCPP), UV-Vis (DMF) λmax, 422 (a Soret band), 515, 552,592 and 648 (Q bands).1H NMR (500 MHz, CDCl3): δ 13.3 (br, 4H), 8.84 (s, 8H), 8.37 (d, J=8.15 Hz, 8H), 8.33 (d, J=8.15 Hz,8H); 13C NMR (126 MHz, CDCl3) δ 119.78 (Cmeso), 128.35 (ArCmeta), 131.00 (C), 134.89(ArCortho), 145.84 (Cα), 167.90 (C=O). Elemental analysis: calculated for C48H30N4O8: C 72.90, H3.82, N 7.09. Found: C 72.11, H 3.67, N 6.75. High-resolution MS, calcd for C48H30N4O8: 790.2064.Found m/z: 790.0068.
60%	With potassium hydroxide; In tetrahydrofuran; methanol; water monomer; for 12h;Reflux;	The obtained methyl ester (0.75g, 0.885mmol) was stirred in THF/MeOH mixed solvent (50mL, 1:1 v/v), and then a solution of aqueous KOH (2.63g, 46.95mmol in H2O 25mL) was added. The resultant mixture was stirred and refluxed for 12h. After cooling down the solution to room temperature, THF and MeOH removed under reduced pressure. Further water was added to the resulting mixture in order to dissolve the solid by heating. Afterwards, the homogeneous solution was acidified by dropwise addition of 1M HCl until no further precipitate was observed. The crystals were then collected using filtration, washed with water and left to dry in air (or in vacuum) (470mg, 0.594mmol, 60 % yield).
	With water monomer; potassium hydroxide; In tetrahydrofuran; at 85℃; for 12h;	Mix 2 g of the synthesized porphyrin ester, 60 mL of THF, 60 mL of methanol, and a prepared potassium hydroxide (KOH) solution (6.8 g KOH plus 60 mL of water), and condense and reflux the mixture at 85 C for 12 h. After cooling to room temperature, adjust the pH of the product to 6~7 with 1M (mol/L) HCl solution, then wash with a large amount of water by suction, and finally vacuum dry at 90C for 12h to obtain tetrakis(4-carboxyphenyl) Porphyrin (H2TCPP).
	With potassium hydroxide; In tetrahydrofuran; methanol; water monomer; at 80℃; for 12h;	Pyrrole (3.0g, 0.043mol) and methyl p-formylbenzoate (6.9g, 0.042mol) were put into a 250ml Pyrrole (3.0g, 0.043mol), methyl p-formylbenzoate (6.9g, 0.042mol) and propionic acid (100mL) were added into a three-neck flask (250mL). The reaction was conducted at 150C for 12h. After reaction, the reaction mixture was cooled to room temperature, yielding black solid. After filtration, the solid was washed with ethanol and dried in vacuum to obtain purple porphyrin ester precursor. The precursor (1.95g) was dissolved in a mixed solvent (120mL, tetrahydrofuran / methanol=1:1). 60ml 2M KOH aqueous solution was added into the mixed solvent. The mixture was heated at 80Cfor 12h. After cooling to room temperature, the mixture was acidified with 1M HCl solution until no solid was produced. Meso-tetra(4-carboxyphenyl) porphyrin was obtained through washing operation and drying treatment. Meso-tetra(4-carboxyphenyl) porphyrin (violet crystal, 32.3%). 1H NMR (DMSO-d6): δ 2.87 ppm (2H, N-H), δ 8.39 ppm (8H, phenyl), δ 8.45 ppm (8H, phenyl), δ 8.91 ppm (8H, pyrrole).

Reference： [1]Dyes and Pigments,2017,vol. 139,p. 651 - 657
[2]International Journal of Molecular Sciences,2016,vol. 17
[3]Angewandte Chemie - International Edition,2018,vol. 57,p. 14852 - 14856
    Angew. Chem.,2018,vol. 130,p. 15068 - 15072,5
[4]Patent: KR2020/28199,2020,A .Location in patent: Paragraph 0111-0112
[5]Angewandte Chemie - International Edition,2022,vol. 61
    Angew. Chem.,2022,vol. 134
[6]Journal of Medicinal Chemistry,2010,vol. 53,p. 4678 - 4690
[7]Russian Journal of Bioorganic Chemistry,2004,vol. 30,p. 89 - 93
[8]Inorganic Chemistry,2021,vol. 60,p. 3988 - 3995
[9]Synthetic Communications,2015,vol. 45,p. 2730 - 2739
[10]Dalton Transactions,2021,vol. 50,p. 9051 - 9058
[11]Chinese Chemical Letters,2022
[12]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6394 - 6397
[13]Tetrahedron,2021,vol. 90
[14]Chemical Communications,2016,vol. 52,p. 13031 - 13034
[15]Applied Catalysis A: General,2021,vol. 611
[16]Tetrahedron,2007,vol. 63,p. 5006 - 5013
[17]Inorganic Chemistry,2016,vol. 55,p. 5287 - 5296
[18]Chemistry - A European Journal,2000,vol. 6,p. 2456 - 2461
[19]Chemistry - A European Journal,2007,vol. 13,p. 8411 - 8427
[20]Materials Research Bulletin,2013,vol. 48,p. 2614 - 2624
[21]Journal of the American Chemical Society,2015,vol. 137,p. 13440 - 13443
[22]Chemistry - A European Journal,2016,vol. 22,p. 3470 - 3477
[23]Inorganic Chemistry,2016,vol. 55,p. 5320 - 5327
[24]Journal of the American Chemical Society,2016,vol. 138,p. 6636 - 6642
[25]Chemistry of Materials,2016,vol. 28,p. 6698 - 6704
[26]Journal of Materials Chemistry A,2016,vol. 4,p. 16818 - 16823
[27]New Journal of Chemistry,2018,vol. 42,p. 1715 - 1724
[28]Angewandte Chemie - International Edition,2018,vol. 57,p. 3493 - 3498
    Angew. Chem.,2018,vol. 130,p. 3551 - 3556,6
[29]Chemical Science,2018,vol. 9,p. 3152 - 3158
[30]Analytical Chemistry,2018,vol. 90,p. 7056 - 7063
[31]Angewandte Chemie - International Edition,2018,vol. 57,p. 8525 - 8529
    Angew. Chem.,2018,vol. 130,p. 8661 - 8665,5
[32]New Journal of Chemistry,2018,vol. 42,p. 11358 - 11363
[33]Angewandte Chemie - International Edition,2019,vol. 58,p. 5692 - 5696
    Angew. Chem.,2019,vol. 58,p. 5748 - 5752,5
[34]Journal of Materials Chemistry A,2019,vol. 7,p. 11355 - 11361
[35]RSC Advances,2019,vol. 9,p. 37003 - 37008
[36]Journal of Materials Chemistry A,2019,vol. 7,p. 26371 - 26377
[37]Angewandte Chemie - International Edition,2020,vol. 59,p. 5326 - 5331
    Angew. Chem.,2020,vol. 132,p. 5364 - 5369,6
[38]Journal of Materials Chemistry A,2020,vol. 8,p. 6034 - 6040
[39]Chemical Communications,2019,vol. 55,p. 11370 - 11373
[40]Journal of the American Chemical Society,2020,vol. 142,p. 12515 - 12523
[41]Chemical Communications,2020,vol. 56,p. 527 - 530
[42]Patent: CN112245579,2021,A .Location in patent: Paragraph 0053-0054
[43]Theranostics,2021,vol. 11,p. 1937 - 1952
[44]Chemical Communications,2021,vol. 57,p. 4035 - 4038
[45]Chemistry - A European Journal,2021,vol. 27,p. 11102 - 11109
[46]Molecular catalysis,2021,vol. 514
[47]Dalton Transactions,2021,vol. 50,p. 13932 - 13942
[48]Angewandte Chemie - International Edition,2022,vol. 61
    Angew. Chem.,2022,vol. 134

7
[ 790655-77-5 ]
[ 14609-54-2 ]
5,10,15,20-tetrakis{4-[(2'-amino-1',4',5',6'-tetrahydropyrimidine)-2-(ethylamino)carbonyl]phenyl}-21H-23H-porphine tetrahydroiodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide Stage #2: 2-(2'-aminoethyl)amine-3',4',5',6'-tetrahydropyrimidine With dmap; triethylamine In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide at 20℃; for 48h;

Reference： [1]Králová, Jarmila; Dvořák, Michal; Král, Vladimír [Journal of Medicinal Chemistry, 2003, vol. 46, # 11, p. 2049 - 2056]

8
[ 159208-86-3 ]
[ 14609-54-2 ]
C₁₄₀H₁₇₈N₁₆O₄₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With pyridine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 72h;

Reference： [1]Finikova, Olga; Galkin, Alexander; Rozhkov, Vladimir; Cordero, Maria; Haegerhaell, Cecilia; Vinogradov, Sergei [Journal of the American Chemical Society, 2003, vol. 125, # 16, p. 4882 - 4893]

9
[ 14609-54-2 ]
[ 796881-89-5 ]
C₁₂₈H₁₄₂N₁₂O₂₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
	With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃;

Reference： [1]Groves, Kevin; Wilson, Andrew J.; Hamilton, Andrew D. [Journal of the American Chemical Society, 2004, vol. 126, # 40, p. 12833 - 12842]
[2]Wilson, Andrew J.; Groves, Kevin; Jain, Rishi K.; Park, Hyung Soon; Hamilton, Andrew D. [Journal of the American Chemical Society, 2003, vol. 125, # 15, p. 4420 - 4421]

10
[ 14609-54-2 ]
[ 194539-82-7 ]
C₁₃₂H₁₉₈N₂₀O₂₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;
23%	With N,N'-dicyclocarbodiimide; benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 18h;

Reference： [1]Location in patent: experimental part Garcia, Guillaume; Sarrazy, Vincent; Sol, Vincent; Morvan, Caroline Le; Granet, Robert; Alves, Sandra; Krausz, Pierre [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 2, p. 767 - 776]
[2]Garcia, Guillaume; Sol, Vincent; Lamarche, Francois; Granet, Robert; Guilloton, Michel; Champavier, Yves; Krausz, Pierre [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 12, p. 3188 - 3192]

11
[ 14609-54-2 ]
[ 879283-71-3 ]
C₁₆₄H₂₅₈N₂₄O₂₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;
41%	With N,N'-dicyclocarbodiimide; benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 18h;

Reference： [1]Location in patent: experimental part Garcia, Guillaume; Sarrazy, Vincent; Sol, Vincent; Morvan, Caroline Le; Granet, Robert; Alves, Sandra; Krausz, Pierre [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 2, p. 767 - 776]
[2]Garcia, Guillaume; Sol, Vincent; Lamarche, Francois; Granet, Robert; Guilloton, Michel; Champavier, Yves; Krausz, Pierre [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 12, p. 3188 - 3192]

12
[ 14609-54-2 ]
C-[8-(tert-butyl-diphenyl-silanyloxymethyl)-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidin-2-yl]-methylamine; hydrochloride [ No CAS ]
C₁₄₈H₁₇₀N₂₀O₈Si₄⁽⁴⁺⁾*4Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridine; dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;

Reference： [1]Kral, Vladimir; Schmidtchen, Franz P.; Lang, Kamil; Berger, Michael [Organic Letters, 2002, vol. 4, # 1, p. 51 - 52]

13
[ 488-43-7 ]
[ 14609-54-2 ]
C₇₂H₈₂N₈O₂₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 20h;
70%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide at 50℃; for 0.5h;

Reference： [1]Kano, Koji; Ishida, Yoshiyuki [Angewandte Chemie - International Edition, 2007, vol. 46, # 5, p. 727 - 730]
[2]Location in patent: scheme or table Ikawa, Yoshiya; Ogawa, Hiroaki; Harada, Hiroyuki; Furuta, Hiroyuki [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 24, p. 6394 - 6397]

14
[ 14609-54-2 ]
5,10,15,20-tetrakis(4-carboxylatophenyl)-21H,23H-porphine tetraammonium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia In methanol	I.9 A mixture of freshly distilled pyrrole and p-carboxyl-benzaldehyde were refluxed in propionic acid for 3 hrs. The precipitated purple crystals were obtained after cooling the mixture, and then it was filtered. The obtained product was of 95 % purity. In order to obtain a more pure product the porphyrin was treated by NaHCO3 and extracted with ethyl acetate and methylene chloride. The organic impurities were transferred into the organic layer whereas the target product as the Na salt was in aq. layer. The further neutralization with HCl to pH<6 led to the formation of crystal acidic porphyrin which was filtered and dried. The green crystals then were treated by 2M ammonia in methanolic solution until the green color changed to the purple one. The title product was crystallized with water-methanol-methylene chloride. Yield 23%.

Reference： [1]Current Patent Assignee: WEIZMANN INSTITUTE OF SCIENCE; TECHNION ISRAEL INSTITUTE OF TECHNOLOGY - US6730666, 2004, B1 Location in patent: Page/Page column 20

15
[ 109-97-7 ]
C₈H₆O₃*H₃N [ No CAS ]
[ 14609-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: pyrrole; C₈H₆O₃*H₃N With propionic acid for 3h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water Stage #3: With hydrogenchloride In water	I.9 A mixture of freshly distilled pyrrole and p-carboxyl-benzaldehyde were refluxed in propionic acid for 3 hrs. The precipitated purple crystals were obtained after cooling the mixture, and then it was filtered. The obtained product was of 95 % purity. In order to obtain a more pure product the porphyrin was treated by NaHCO3 and extracted with ethyl acetate and methylene chloride. The organic impurities were transferred into the organic layer whereas the target product as the Na salt was in aq. layer. The further neutralization with HCl to pH<6 led to the formation of crystal acidic porphyrin which was filtered and dried. The green crystals then were treated by 2M ammonia in methanolic solution until the green color changed to the purple one. The title product was crystallized with water-methanol-methylene chloride. Yield 23%.

Reference： [1]Current Patent Assignee: WEIZMANN INSTITUTE OF SCIENCE; TECHNION ISRAEL INSTITUTE OF TECHNOLOGY - US6730666, 2004, B1 Location in patent: Page/Page column 20

16
[ 14609-54-2 ]
[5,10,15,20-tetrakis(4-methoxycarbonylphenyl)porphyrinato]-Pd(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium dichloride In N,N-dimethyl-formamide at 155℃; for 0.25h;

Reference： [1]Farha, Omar K.; Shultz, Abraham M.; Sarjeant, Amy A.; Nguyen, Sonbinh T.; Hupp, Joseph T. [Journal of the American Chemical Society, 2011, vol. 133, # 15, p. 5652 - 5655]

17
[ 14609-54-2 ]
5,10,15,20-tetrakis(4-HOOC-C₆H₄)porphin iron [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With iron(III) chloride In water at 180℃; for 168h; Autoclave;
	With iron(III) chloride In N,N-dimethyl-formamide for 2h; Reflux;

Reference： [1]Location in patent: experimental part Chen, Wentong; Luo, Zhigang; Chen, Hualong; Kuang, Hanmao; Liu, Dongsheng [Journal of Chemical Research, 2012, vol. 36, # 2, p. 72 - 74]
[2]Location in patent: experimental part Granados-Oliveros, Gilma; Páez-Mozo, Edgar Alberto; Martínez Ortega, Fernando; Piccinato, Marileneturini; Silva, Fausto Neves; Guedes, Carmen Luísa Barbosa; Di Mauro, Eduardo; Costa, Marcello Ferreira Da; Ota, André Tsutomu [Journal of Molecular Catalysis A: Chemical, 2011, vol. 339, # 1-2, p. 79 - 85]

18
[ 14609-54-2 ]
[ 55216-11-0 ]
C₄₈H₃₀N₄O₈*2C₆₃H₁₁₂O₃₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tetrakis(4-carboxyphenyl)porphyrin; 2,3,6-trimethyl-beta-cyclodextrin With sodium hydroxide In water Stage #2: With hydrogenchloride In water
	for 0.333333h; Milling;

Reference： [1]Location in patent: experimental part Tsuchiya, Youichi; Shiraki, Tomohiro; Matsumoto, Takashi; Sugikawa, Kouta; Sada, Kazuki; Yamano, Akihito; Shinkai, Seiji [Chemistry - A European Journal, 2012, vol. 18, # 2, p. 456 - 465]
[2]Ikeda, Atsushi; Hino, Shodai; Mae, Tomoya; Tsuchiya, Yuki; Sugikawa, Kouta; Tsukamoto, Manami; Yasuhara, Kazuma; Shigeto, Hajime; Funabashi, Hisakage; Kuroda, Akio; Akiyama, Motofusa [RSC Advances, 2015, vol. 5, # 127, p. 105279 - 105287]

19
[ 14609-51-9 ]
[ 14609-54-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 4782 - 4787

20
[ 14609-54-2 ]
PCN-222(Zn) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With N-formyldiethylamine; zirconium(IV) chloride; benzoic acid; zinc(II) chloride at 120℃; for 48h;

Reference： [1]Feng, Dawei; Gu, Zhi-Yuan; Li, Jian-Rong; Jiang, Hai-Long; Wei, Zhangwen; Zhou, Hong-Cai [Angewandte Chemie - International Edition, 2012, vol. 51, # 41, p. 10307 - 10310,4][Angewandte Chemie, 2011, vol. 124, # 41, p. 10453 - 10456,4] Feng, Dawei; Gu, Zhi-Yuan; Li, Jian-Rong; Jiang, Hai-Long; Wei, Zhangwen; Zhou, Hong-Cai [Angewandte Chemie - International Edition, 2012, vol. 51, # 41, p. 10307 - 10310][Angew. Chem., 2011, vol. 124, # 41, p. 10453 - 10456,4]

21
[ 14609-54-2 ]
PCN-222 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With N-formyldiethylamine; zirconium(IV) chloride; benzoic acid at 120℃; for 48h;

Reference： [1]Feng, Dawei; Gu, Zhi-Yuan; Li, Jian-Rong; Jiang, Hai-Long; Wei, Zhangwen; Zhou, Hong-Cai [Angewandte Chemie - International Edition, 2012, vol. 51, # 41, p. 10307 - 10310,4][Angewandte Chemie, 2011, vol. 124, # 41, p. 10453 - 10456,4] Feng, Dawei; Gu, Zhi-Yuan; Li, Jian-Rong; Jiang, Hai-Long; Wei, Zhangwen; Zhou, Hong-Cai [Angewandte Chemie - International Edition, 2012, vol. 51, # 41, p. 10307 - 10310][Angew. Chem., 2011, vol. 124, # 41, p. 10453 - 10456,4]

22
[ 14609-54-2 ]
[ 540-51-2 ]
meso-tetrakis<4-<(2-bromoethoxy)carbonyl>phenyl>porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Cooling with ice;

Reference： [1]Zhang, Hui; Liu, Qiang; Li, Jing; Qu, Da-Hui [Organic Letters, 2013, vol. 15, # 2, p. 338 - 341]

23
cobalt(II) chloride hexahydrate [ No CAS ]
[ 14609-54-2 ]
[[meso-tetra(4-carboxyphenyl)porphyrinato]cobalt(III)]Cl·7H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: cobalt(II) chloride hexahydrate; tetrakis(4-carboxyphenyl)porphyrin In dimethyl sulfoxide for 24h; Reflux; Stage #2: With hydrogenchloride In water
80%	In dimethyl sulfoxide for 24h; Reflux;

Reference： [1]Nakazono, Takashi; Parent, Alexander Rene; Sakai, Ken [Chemical Communications, 2013, vol. 49, # 56, p. 6325 - 6327]
[2]Fu, Shao; Liu, Yongdong; Ding, Yong; Du, Xiaoqiang; Song, Fangyuan; Xiang, Rui; Ma, Baochun [Chemical Communications, 2014, vol. 50, # 17, p. 2167 - 2169]

24
[ 919524-44-0 ]
[ 14609-54-2 ]
C₁₀₀H₁₃₈N₈O₂₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 1,3-bis(2-(2-methoxyethoxy)ethoxy)propane-2-amine In N,N-dimethyl-formamide at 20℃; for 48h;	General procedure: Porphyrin compound (0.16mmol) and EDCI (148 mg,0.77 mmol), HOBt (117 mg, 0.77 mmol) were dissolved in40 ml dry DMF. The mixture were cooled to 0 oC and stirredfor 0.5 h before removal of the ice bath. Subsequently, compound3 (283 mg, 0.96 mmol) was added. The reaction wasstirred for 2 d at room temperature. After that, the solventDMF was evaporated under reduced pressure. The solid mixturewas dried under vacuum at 60 oC, and then purified bycolumn chromatography on silica gel to yield pure redproduct.Porphyrin P1:yield 70%. 1H-NMR (300 Hz, CDCl3, 298K): (ppm) 8.85 (s, 8 H), 8.31 (d, J = 7.8 Hz, 8 H), 8.24 (d,J = 7.8 Hz, 8 H), 7.18 (d, J = 8.4 Hz, 4 H), 4.66-4.64 (m, 16H), 3.77-3.75 (m, 16 H), 3.73-3.72 (m, 16 H), 3.61-3.60 (m,32 H), 3.39 (s, 24 H). Anal. Calcd for C100H138N8O28: C,63.21; H, 7.32; N, 5.90. found: C, 63.03; H, 7.65; N, 5.82.m/z [MALDITOF]: 1900.0 (MH+).

Reference： [1]Liu, Jinjun; Zhang, Licui; Du, Xiaojuan; Cui, Fengxia; Du, Chunlei; Gao, Baoxiang [Letters in Organic Chemistry, 2013, vol. 10, # 5, p. 342 - 347]

25
[ 1539-42-0 ]
[ 14609-54-2 ]
5,10,15,20-tetra[p-N,N-bis(2-pyridylmethyl)aminophenyl]porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride	Preparation of 5,10,15,20-tetra[p-N,N-di(2-pyridylmethyl)aminophenyl] porphyrinato zinc complex Zn-Porphyrin-4-DPA (2) General procedure: According to the published procedure [23], 5,10,15,20-tetra[p-N,N-di (2-pyridylmethyl)aminophenyl]porphyrin (Porphyrin-4-DPA) was prepared through the hydrolyzation of 5,10,15,20-tetra(4-cyanophenyl)porphyrin followed by the reaction of 5,10,15,20-tetra(4-carboxylphenyl)porphyrin with thionyl chloride and DPA. With the newly prepared Porphyrin-4-DPA (30 g, 0.02 mol) instead of Porphyrin-2-DPA as starting material, utilization of the above described procedure employed to prepare 1 led to the isolation of Zn-Porphyrin-4-DPA (2) in the yield of 76 , 24 g. 1H NMR (CDCl3/Py-d6, 400 Hz) δ 8.71 (s, 8 H), 8.59 (d, 4 H, J=4 Hz), 8.52 (d, 4 H, J=4 Hz), 8.10 (d, 8 H, J=8 Hz), 7.91 (d, 8 H J=8 Hz), 7.69 (t, 8 H, J=16 Hz), 7.49 (d, 4 H, J=8 Hz), 7.32 (d, 4 H J=8 Hz), 7.18 (4 H, obscured by the strong residual CHCl3 signal), 4.97 (s, 16 H); MS (MALDI-TOF): an isotopic cluster peaking at m/z 1580.38, [Calcd. For [M+H]+ 1580.62]; Anal. Calcd for C96H72N16O4Zn: C, 73.02; H, 4.60; N, 14.19. Found: C, 73.05; H, 4.32; N, 14.27.

Reference： [1]Chen, Yuting; Jiang, Jianzhuang [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 116, p. 418 - 423]

26
[ 6066-82-6 ]
[ 14609-54-2 ]
C₆₄H₄₂N₈O₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; dimethyl sulfoxide at 20℃; for 50h; Cooling with ice;
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 48h; Reflux;

Reference： [1]Vega, Daniel L.; Lodge, Patrick; Vivero-Escoto, Juan L. [International Journal of Molecular Sciences, 2016, vol. 17, # 1]
[2]Reanprayoon, Chawanwit; Gasiorowski, Jacek; Sukwattanasinitt, Mongkol; Sariciftci, Niyazi Serdar; Thamyongkit, Patchanita [RSC Advances, 2014, vol. 4, # 6, p. 3045 - 3050]

27
[ 18908-66-2 ]
[ 14609-54-2 ]
C₈₀H₉₄N₄O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 20h;

Reference： [1]Duan, Pengfei; Yanai, Nobuhiro; Kimizuka, Nobuo [Journal of the American Chemical Society, 2013, vol. 135, # 51, p. 19056 - 19059]

28
[ 14609-54-2 ]
[ 22112-83-0 ]
4-(10,15,20-tris(4-(methoxycarbonyl)phenyl)porphyrin-5-yl)benzoic acid [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1864 - 1867

29
[ 14609-54-2 ]
[ 480445-08-7 ]
C₁₉₂H₂₉₀N₈O₁₆ [ No CAS ]
C₁₅₆H₂₂₅N₇O₁₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 13.7% 2: 50%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20℃; for 15h; Inert atmosphere; Darkness;

Reference： [1]Presolski, Stanislav I.; Van Der Weegen, Rob; Wiesfeld, Jan J.; Meijer [Organic Letters, 2014, vol. 16, # 7, p. 1864 - 1867]

30
2-azidoethanamine trifluoroacetic acid salt [ No CAS ]
[ 14609-54-2 ]
C₅₆H₄₆N₂₀O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 4h;

Reference： [1]Clave, Guillaume; Chatelain, Gregory; Filoramo, Arianna; Gasparutto, Didier; Saint-Pierre, Christine; Le Cam, Eric; Pietrement, Olivier; Guerineau, Vincent; Campidelli, Stephane [Organic and Biomolecular Chemistry, 2014, vol. 12, # 17, p. 2778 - 2783] Chatelain; Clavé; Saint-Pierre; Gasparutto; Campidelli [Organic and Biomolecular Chemistry, 2017, vol. 15, # 29, p. 6257 - 6263]

31
gallium(III) trichloride [ No CAS ]
[ 14609-54-2 ]
ClGa(III)(5,10,15,20-tetrakis-(4-carboxyphenyl)porphyrin) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	In N,N-dimethyl-formamide at 100℃; for 0.25h;	Synthesis of gallium 5,10,15,20-tetrakis-(4-carboxyphenyl)porphyrin The metal free 5,10,15,20-tetrakis-(4-carboxyphenyl) porphyrin was synthesized according to literature [11]. The synthesis of ClGa(III)TCPP is as follows: DMF was brought to reflux temperature in a two necked flask while stirring and then H2TCPP (4 g, 5.1 mmol) was added and temperature brought to 100 °C. Then gallium chloride (1 g, 5.6 mmol) was added and heating continued for 15 min. The completion of the reaction was checked using UV/Vis spectrophotometer. The four bands in the Q band region of the metal free H2TCPP collapse into two on metalation. The reaction vessel was then allowed to cool in ice water. Ice cold water (500 mL) was added onto the resulting partially crystalline precipitate, which was then filtered and washed with water then air dried. The product was purified by column chromatography.

Reference： [1]Managa, Muthumuni; Antunes, Edith; Nyokong, Tebello [Polyhedron, 2014, vol. 76, p. 94 - 101]

32
zinc(II) nitrate hexahydrate [ No CAS ]
[ 14609-54-2 ]
C₄₈H₂₄N₄O₈^(6-)*3Zn⁽²⁺⁾*3H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With pyridine In N,N-dimethyl-formamide at 90℃; for 24h; Autoclave;	Synthesis of Zn₂(ZnTCPP)3H₂O, 3 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin (H2TCPP), 1 (0.04 mmol) dissolved in 40 ml of N,N-dimethylformamide (DMF) was mixed with 5 ml of Zn(NO3)26H2O, 2 (0.16 mmol) DMF solution and pyridine (0.16 mmol). The mixture was transferred into a 50 ml Teflon-lined pressure vessel and heated at 90°C for 24 hours and cooled down to room temperature at 3°C/hour. The product was filtered and rinsed with DMF. Purple plate-shaped crystals (Fig. S1a) formulated as Zn2(ZnTCPP)3H2O, 3 were collected (yield 43%). We also found bipyramidal-shaped crystals composed of stacked plates (Fig. S1b) in the same synthetic batch. Elemental analysis : Found (%), C 54.78, H 3.84, N 7.91, Calc. (%) for Zn2(ZnTCPP)3H2O*3DMF, C 54.58, H4.10, N 7.82.

Reference： [1]Makiura, Rie; Usui, Ryo; Pohl, Ehmke; Prassides, Kosmas [Chemistry Letters, 2014, vol. 43, # 7, p. 1161 - 1163]

33
[ 617-84-5 ]
zinc(II) nitrate hexahydrate [ No CAS ]
[ 14609-54-2 ]
[ 608528-49-0 ]
[Zn₂(Zn(tetrakis(4-carboxyphenyl)porphyrin))(bis(5-pyridyl-2-methyl-3-thienyl)cyclopentene)_0.85(N,N-diethylformamide)_1.15](N,N-diethylformamide)_5.15(H₂O)_7.25 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	Stage #1: N-formyldiethylamine; zinc(II) nitrate hexahydrate; tetrakis(4-carboxyphenyl)porphyrin In ethanol for 0.166667h; Sonication; Stage #2: 1,2‐bis(2‐methyl‐5‐(pyridin‐4‐yl)thiophen‐3‐yl)cyclopent‐1‐ene With nitric acid In ethanol at 80℃; for 14h;

Reference： [1]Williams, Derek E.; Rietman, Joseph A.; Maier, Josef M.; Tan, Rui; Greytak, Andrew B.; Smith, Mark D.; Krause, Jeanette A.; Shustova, Natalia B. [Journal of the American Chemical Society, 2014, vol. 136, # 34, p. 11886 - 11889]

34
[ 484-17-3 ]
[ 14609-54-2 ]
meso-tetra-(4-benzoate-9-phenanthryl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In tetrahydrofuran for 120h;	2.2.1. Meso-tetra-(4-benzoate,9-phenanthryl)-porphyrin (TB9FP, 1) TB9FP (1) wassynthesized (scheme 1) by adapting the procedure used by Vargas et al. [16]. The esterification was carried out by passing a stream of dry gaseous HCl through a solution of meso-tetra-(4-carboxyphenyl)porphyrin (TCPP, 201.3 mg, 0.255 mM) and 9-phenanthrol(497.0 mg, 2.56 mM) in THF (50 mL) without heating for five days. The reaction progress was followed by thin-layer chromatography and the crude product was separated and purified by column chromatography (CHCl3/MeOH, 2 : 8). The purple crystals were washed with methanol. Yield: 41% (156.6 mg).FT-IR (KBr, thin film) νmax (cm-1): 3435 (N-H), 3138-2853 (=C-H), 1744 (C=O), 1400(C-N), 1384 (C-O-C), 1116 (C-O-C), 1102 (N-H), 802 (N-H), 617 (=C-H). MS: m/z1293.80 (M + H)+ Phenantrol (cal: 1292.41); 1496.53 (M)+. Analysis, C52H31N2O4 calculated%C 69.065, %H 5.190, %N 1.870; found: %C 69.032, %H 5.236, %N 1.770. 1HNMR (500 MHz, CDCl3, δ, J = Hz): -2.808 (s, 4H, imino protons), 8.824 (s, 8H, pyrrolsprotons), 8.652 (d, J = 7.5, 4H, H3), 8.581 (d, J = 7.5, 4H, H4), 8.450 (d, J = 7.5, 4H, H5),8.361 (d, J = 7.5, 4H, H6), 8.305 (d, J = 7.5, 4H, H7), 7.753 (d, J = 7.5, 4H, H8), 7.681 (t,J = 7.5, 4H, H9), 7.622 (t, J = 7.5, 4H, H10), 7.535 (t, J = 7.5, 4H, H11), 7.496 (t, J = 7.5,4H, H12), 6.972 (s, 4H, H13). 13C NMR (200 MHz, CDCl3), δ = ppm: 166.688 (C=O, C1),152.684 (C-N, C2), 146.721 (C-O, C3), 134.566 (C4), 132.910 (C5), 131.309 (C6),129.879 (C7), 129.583 (C8), 128.003 (C9), 127.287 (C10), 127.160 (C11), 126.911 (C12),126.610 (C13), 126.472 (C14), 126.400 (C15), 124.270 (C16), 122.566 (C17), 122.517(C18), 122.499 (C19), 119.416 (C20), 102.649 (C21). UV-vis (CHCl3), λmax (nm): 420,516, 550, 590, 648.

Reference： [1]Oviedo, Olycen; Zoltan, Tamara; Vargas, Franklin; Inojosa, Marcel; Vivas, Julio C. [Journal of Coordination Chemistry, 2014, vol. 67, # 10, p. 1715 - 1730]

35
[ 14609-54-2 ]
[ 69-89-6 ]
C₄₈H₃₀N₄O₈*C₅H₄N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In aq. buffer;pH 11.21;	General procedure: The titration experiments were carried out according to the proceduredescribed previously [33]. A freshly prepared 2 cm3 solutionof 0.025 mol dm3 TRIS, containing appropriate concentration of thechosen porphyrin (chlorophyll a solution in acetone) was titratedmanually by successive additions of ligands, dissolved as well in0.025 mol dm3 TRIS (10 mM stock solutions of theophylline,theobromine and <strong>[69-89-6]xanthin</strong>e at pH = 8.46, 10.69 and 11.21, respectively,to improve their solubility in water).

Reference： [1]Journal of Molecular Structure,2015,vol. 1081,p. 224 - 232

36
[ 58-55-9 ]
[ 14609-54-2 ]
C₄₈H₃₀N₄O₈*C₇H₈N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In aq. buffer	General procedure: The titration experiments were carried out according to the proceduredescribed previously [33]. A freshly prepared 2 cm3 solutionof 0.025 mol dm3 TRIS, containing appropriate concentration of thechosen porphyrin (chlorophyll a solution in acetone) was titratedmanually by successive additions of ligands, dissolved as well in0.025 mol dm3 TRIS (10 mM stock solutions of theophylline,theobromine and xanthine at pH = 8.46, 10.69 and 11.21, respectively,to improve their solubility in water).

Reference： [1]Makarska-Bialokoz, Magdalena [Journal of Molecular Structure, 2015, vol. 1081, p. 224 - 232]

37
[ 83-67-0 ]
[ 14609-54-2 ]
C₄₈H₃₀N₄O₈*C₇H₈N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In aq. buffer	General procedure: The titration experiments were carried out according to the proceduredescribed previously [33]. A freshly prepared 2 cm3 solutionof 0.025 mol dm3 TRIS, containing appropriate concentration of thechosen porphyrin (chlorophyll a solution in acetone) was titratedmanually by successive additions of ligands, dissolved as well in0.025 mol dm3 TRIS (10 mM stock solutions of theophylline,theobromine and xanthine at pH = 8.46, 10.69 and 11.21, respectively,to improve their solubility in water).

Reference： [1]Makarska-Bialokoz, Magdalena [Journal of Molecular Structure, 2015, vol. 1081, p. 224 - 232]

38
iron(III) chloride hexahydrate [ No CAS ]
[ 14609-54-2 ]
5,10,15,20-tetrakis (4-benzoic acid) porphyrinato iron (III) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide for 2h; Reflux;	2.2.2 Synthesis of TCPPFe and adsorption on SiO₂ The TCPPFe was synthesized as follows: the metal-free porphyrin (0.33mmol) was mixed with iron (III) chloride hexahydrate in 70mL of N,N′-dimethylformamide (DMF) for 2h in reflux system. The DMF was removed by distillation and the TCPPFe was precipitated in water. The precipitate was dissolved in 0.100M NaOH and recrystallized for adding 1.00M HCl. Finally, the TCPPFe was filtered and dried at room temperature. The TCPP and TCPPFe were characterized by UV-vis and EPR spectroscopy. The adsorption of TCPPFe on the SiO2 was performed as follows: TCPPFe was added to a mixture (20mL of absolute ethanol, 3mL of tetraethoxysilane (TEOS) and 0.5mL of distilled water) at pH 3 (adjusted with HNO3), the mixture was refluxed for 24h, the solvent was evaporated and, finally, the solid was dried at room temperature [18].

Reference： [1]Diaz-Uribe, Carlos E.; Vallejo L., William A.; Miranda, Jarol [Journal of Photochemistry and Photobiology A: Chemistry, 2014, vol. 294, p. 75 - 80]

39
[ 57260-73-8 ]
[ 14609-54-2 ]
5,10,15,20-tetrakis-2-([4-tert-butylbenzamido]ethylcarbamate)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: N-BOC-1,2-diaminoethane With dmap In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;

Reference： [1]Daly; Al-Sabi; Kinsella; Nolan; Dolly [Chemical Communications, 2015, vol. 51, # 6, p. 1066 - 1069]

40
[ 75178-96-0 ]
[ 14609-54-2 ]
5,10,15,20-tetrakis-3-([4-tert-butylbenzamido]propylcarbamate)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: N-Boc-1,3-diaminopropane With dmap In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 1h; Stage #2: N-Boc-1,3-diaminopropane In chloroform at 20℃; for 24h; Inert atmosphere; Darkness;

Reference： [1]Daly; Al-Sabi; Kinsella; Nolan; Dolly [Chemical Communications, 2015, vol. 51, # 6, p. 1066 - 1069]
[2]Li, Zhiliang; Zeman, Charles J.; Valandro, Silvano R.; Bantang, Jose Paolo O.; Schanze, Kirk S. [Journal of the American Chemical Society, 2019, vol. 141, # 32, p. 12610 - 12618]

41
[ 68076-36-8 ]
[ 14609-54-2 ]
5,10,15,20-tetrakis-4-([4-tert-butylbenzamido]butylcarbamate)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 1-amino-4-[(tert-butyloxycarbonyl)amino]butane With dmap In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;

Reference： [1]Daly; Al-Sabi; Kinsella; Nolan; Dolly [Chemical Communications, 2015, vol. 51, # 6, p. 1066 - 1069]

42
[ 26690-80-2 ]
[ 14609-54-2 ]
5,10,15,20-tetrakis-2-([4-tert-butylbenzester]ethylcarbamate)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: 2-(N-tert-butoxycarbonylamino)ethanol In N,N-dimethyl-formamide at 0 - 20℃; for 36.5h; Inert atmosphere;

Reference： [1]Daly; Al-Sabi; Kinsella; Nolan; Dolly [Chemical Communications, 2015, vol. 51, # 6, p. 1066 - 1069]

43
[ 14609-54-2 ]
[ 117499-16-8 ]
5,10,15,20-tetrakis-2-([di-tert-butyl(benzoylazanediyl)]bis((ethane-2,1-diyl)dicarbamate))porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: bis(2-tert-butyloxycarbonylaminoethyl)amine With dmap In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;

Reference： [1]Daly; Al-Sabi; Kinsella; Nolan; Dolly [Chemical Communications, 2015, vol. 51, # 6, p. 1066 - 1069]

44
[ 14609-54-2 ]
[ 108-00-9 ]
meso-tetrakis<4-<<<2-(N,N-dimethylamino)ethyl>amino>carbonyl>phenyl>porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: N,N-dimethylethylenediamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;

Reference： [1]Daly; Al-Sabi; Kinsella; Nolan; Dolly [Chemical Communications, 2015, vol. 51, # 6, p. 1066 - 1069]

45
[ 14609-54-2 ]
[ 109-55-7 ]
meso-tetrakis<4-<<<3-(N,N-dimethylamino)propyl>amino>carbonyl>phenyl>porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: 1-amino-3-(dimethylamino)propane In N,N-dimethyl-formamide at 0 - 20℃; for 0.333333h; Inert atmosphere;

Reference： [1]Daly; Al-Sabi; Kinsella; Nolan; Dolly [Chemical Communications, 2015, vol. 51, # 6, p. 1066 - 1069]

46
aluminium(III) chloride hexahydrate [ No CAS ]
[ 14609-54-2 ]
[Al₂(OH)₂(4,4′,4″,4‴-(porphyrin-5,10,15,20-tetrayl)tetrabenzoate)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water at 160℃; for 0.666667h; Microwave irradiation;
	High pressure;
	In water at 180℃; for 24h; Autoclave;	Preparation of Al-TCPP-Bulk, Al-TCPP-Cara and Al-TCPP-MOL Al-TCPP in the bulk form (hereafter denoted as Al-TCPP-Bulk) and carambola shape (denoted as Al-TCPP-Cara) were hydrothermally synthesized by using AlCl3·6H2O and TCPP as the raw materials at 180 °C in the presence of water (Fig. 1a). In a typical synthesis of Al-TCPP-Bulk, 144 mg AlCl3·6H2O (0.8 mmol) and 60 mg TCPP (0.08 mmol) were added to 30 mL of deionized water, and then the mixture was stirred for 30 minutes. The resulting mixture was transferred to a 100 mL vessel and maintained at 180 °C for 24 h. After cooling naturally to room temperature, the precipitates were centrifuged and washed twice with DMF and acetone. Finally, the resulting powder was placed in vacuum oven at 60 °C for drying overnight. Al-TCPP-Cara was prepared with the same synthesis procedures of Al-TCPP-Bulk except that the volume of DI water was changed to 60 mL. Al-TCPP-MOL (MOL: metal-organic layers) was prepared by the exfoliation of Al-TCPP-Bulk. In a typical synthesis, 10 mg Al-TCPP-Bulk was added into 10 mL ethanol. The mixture was ultrasonicated at a water bath for 1.5 hours. After the ultrasonication, the suspension was centrifuged at 8000 rpm for 8 minutes and the supernatant was dried through rotary evaporation. The powder was collected and then re-dispersed in DI water. Afterwards, the suspension was freeze dried overnight and the resultant Al-TCPP-MOL was obtained.

Reference： [1]Zhao, Yingbo; Kornienko, Nikolay; Liu, Zheng; Zhu, Chenhui; Asahina, Shunsuke; Kuo, Tsung-Rong; Bao, Wei; Xie, Chenlu; Hexemer, Alexander; Terasaki, Osamu; Yang, Peidong; Yaghi, Omar M. [Journal of the American Chemical Society, 2015, vol. 137, # 6, p. 2199 - 2202]
[2]Lions; Tommasino; Chattot; Abeykoon; Guillou; Devic; Demessence; Cardenas; Maillard; Fateeva [Chemical Communications, 2017, vol. 53, # 48, p. 6496 - 6499]
[3]Yu, Hui; Wu, Xiang; Mu, Qiaoqiao; Wei, Zhihe; Gu, Yindong; Yuan, Xuzhou; Lu, Yongtao; Deng, Zhao; Peng, Yang [Chinese Chemical Letters, 2021, vol. 32, # 12, p. 3833 - 3836]

47
[ 557-34-6 ]
[ 14609-54-2 ]
5,10,15,20-tetrakis(4-carboxyphenyl)porphyrinatozinc(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; N,N-dimethyl-formamide for 2h; Reflux;
	In N,N-dimethyl-formamide for 12h; Reflux;	2.1.2 General Procedure of the Synthesis of Metalloporphyrins General procedure: Metalloporphyrins were prepared by refluxing porphyrins (0.33 mmol) with FeCl3, CoCl2, MnCl2, CuCl2, or Zn(OAc)2 (1.82 mmol) in N,N'-dimethylformamide (DMF, 70 mL) for 12 h. DMF was removed by distillation and the metalloporphyrins were precipitated by adding water. The precipitate was dissolved in 0.1 M NaOH solution and recrystallized by adding 1 M HCl solution. Finally, metalloporphyrins were filtered and dried under vacuum.
	In N,N-dimethyl-formamide

Reference： [1]Wang, Huigang; Fu, Ying; Han, Tiehu; Wan, Junmin; Zheng, Xuming [RSC Advances, 2015, vol. 5, # 42, p. 33570 - 33578]
[2]Sun, Weizhi; Liu, Yaojie; Zhang, Haibo; Xian, Mo; Liu, Huizhou [Catalysis Letters, 2015, vol. 145, # 11, p. 1991 - 1999]
[3]Shen, Hai M.; Ye, Hong L.; Wang, Qin; Hu, Meng Y.; Liu, Lei; She, Yuan B. [Journal of Porphyrins and Phthalocyanines, 2021, vol. 25, # 4, p. 314 - 322]

48
manganese(II) chloride tetrahydrate [ No CAS ]
[ 14609-54-2 ]
manganase(II)-5,10,15,20-tetra(4-carboxyphenyl)porphine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: manganese(II) chloride tetrahydrate; tetrakis(4-carboxyphenyl)porphyrin In N,N-dimethyl-formamide for 12h; Reflux; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃; for 72h;	2.2 The Porphyrin Synthesis A solution of H2TCPP 0.42 g (0.50 mmol) and MnCl2-4H2O (0.24 g, 1.00 mmol) in 50 mL of DMF was refluxed for 12 h. After the mixture was cooled to room temperature, 500 mL of H2O was added. The resultant precipitate was filtered and washed with 200 mL of H2O for three times. The obtained solid was dissolved in CHCl3, followed by washing three times with water. The organic layer was dried over anhydrous magnesium sulfate and evaporated to afford quantitative dark green crystals [27]. In the next stage, 0.45 g (0.50 mmol) of the latter product was dissolved in 20 mL of THF. To this, 1.60 g of NaOH in 20 mL of water was added and the solution was stirred at room temperature for 3 days. At the end of this period, THF was removed by rotary evaporation. The crude porphyrin was treated with 20 mL of 2 N HCl solutions, yielding a green precipitate, which was filtered, washed with water, and dried. Protonated porphyrin was neutralized by adding 10 mL of pyridine and subsequently removed by vacuum distillation. Then, purple solid was washed with water and dried under a vacuum. Yield: 0.39 g (88 %).

Reference： [1]Zhang, Weijie; Jiang, Pingping; Wang, Ying; Zhang, Jian; Zhang, Pingbo [Catalysis Letters, 2015, vol. 145, # 2, p. 589 - 595]

49
[ 109-97-7 ]
[ 1571-08-0 ]
[ 14609-54-2 ]

Yield	Reaction Conditions	Operation in experiment
35%	Stage #1: pyrrole; methyl 4-formylbenzoate With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1.5h; Darkness; Stage #2: With chloranil In dichloromethane Stage #3: With sodium hydroxide	2.2 The Porphyrin Synthesis The 5, 10, 15, 20-tetrakis(4-carboxyphenyl)porphyrin (H2-TCPP) was synthesized by the modified Lindsey method[26], involving NaOH hydrolysis of the corresponding intermediate. Thus, 1.22 g (7.46 mmol) of 4-carbomethoxybenzaldehyde and 0.50 g of distilled pyrrole (7.46 mmol) were added to 750 mL of dry CH2Cl2 for 30 min. Then, BF3 etherate (92 uL) was added via syringe, and the reaction mixture was protected from light. After stirring at room temperature for 1 h, 1.37 g (5.62 mmol) of p-chloranil was added in the solid form and the solution was stirred overnight.The solution was concentrated to a small volume using a rotary evaporator. To this solution, silica gel (60-200 mesh) was added and the slurry was evaporated to give a dry black powder, which was loaded on a silica column using CHCl3. First CHCl3 fraction removed anypoly (pyrrole) impurity and the porphyrin was eluted with 2-4 % acetone in CHCl3. It was then further purified by recrystallization from a 1:4 CHCl3/methanol mixture (v/v).Yield: 0.55 g (35 %). 1H NMR (400 MHz, CDCl3) d9.08-8.64 (m, 8H), 8.62-8.37 (m, 8H), 8.39-8.13 (m, 8H),4.34-3.88 (m, 12H), -2.79 (s, 2H).
	Stage #1: pyrrole; methyl 4-formylbenzoate With propionic acid at 160℃; for 12h; Stage #2: With potassium hydroxide In tetrahydrofuran; methanol; water at 80℃; for 12h;
	Stage #1: pyrrole; methyl 4-formylbenzoate With propionic acid at 140℃; for 12h; Stage #2: With potassium hydroxide In tetrahydrofuran; methanol; water at 80℃; for 12h;

	Stage #1: pyrrole; methyl 4-formylbenzoate With propionic acid In dimethyl sulfoxide at 130℃; for 2h; Stage #2: With potassium hydroxide In tetrahydrofuran; methanol at 80℃; for 12h;
2.4 g	Stage #1: pyrrole; methyl 4-formylbenzoate With propionic acid at 140℃; for 15h; Stage #2: With water; potassium hydroxide In tetrahydrofuran; methanol

Reference： [1]Zhang, Weijie; Jiang, Pingping; Wang, Ying; Zhang, Jian; Zhang, Pingbo [Catalysis Letters, 2015, vol. 145, # 2, p. 589 - 595]
[2]Fang, Xinzuo; Jiao, Long; Yu, Shu-Hong; Jiang, Hai-Long [ChemSusChem, 2017, vol. 10, # 15, p. 3019 - 3024]
[3]Wang, Bing; Liu, Shuo; Liu, Lin; Song, Wen-Wei; Zhang, Yue; Wang, Shi-Ming; Han, Zheng-Bo [Journal of Materials Chemistry A, 2021, vol. 9, # 5, p. 2948 - 2958]
[4]Li, Ang; Chen, Siyuan; Yang, Fucheng; Gao, Hongyi; Dong, Cheng; Wang, Ge [Inorganic Chemistry, 2021, vol. 60, # 23, p. 18337 - 18346]
[5]Dang, Nam N.; Dong, Hieu C.; Luu, Loc C.; Nguyen, Hung N.; Nguyen, My V.; Nguyen, Tuyet A. T.; Truong, Vy T. N. [New Journal of Chemistry, 2022, vol. 46, # 2, p. 632 - 641]

50
[ 1571-08-0 ]
[ 14609-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: propionic acid / 1 h / 80 - 140 °C 2: potassium hydroxide / tetrahydrofuran / 24 h / Reflux
	Multi-step reaction with 2 steps 1: propionic acid / 1.5 h / 140 °C 2: potassium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate / 48 h / 66 °C
	Multi-step reaction with 2 steps 1: propionic acid / 12 h / Reflux 2: sodium hydroxide / lithium hydroxide monohydrate; tetrahydrofuran; methanol / 12 h / Reflux

	Multi-step reaction with 2 steps 1: propionic acid / 140 °C 2: potassium hydroxide / tetrahydrofuran; methanol; lithium hydroxide monohydrate / 12 h / Reflux
	Multi-step reaction with 2 steps 1: propionic acid / 12 h / Reflux; Inert atmosphere 2: potassium hydroxide / tetrahydrofuran; methanol; lithium hydroxide monohydrate / 16 h / Reflux
	Multi-step reaction with 2 steps 1: propionic acid / 12 h / 140 °C / Darkness 2: potassium hydroxide / tetrahydrofuran; methanol; lithium hydroxide monohydrate / 12 h / 85 °C
	Multi-step reaction with 2 steps 1: 12 h / Schlenk technique; Inert atmosphere; Reflux 2: potassium hydroxide / tetrahydrofuran; methanol / 12 h / Reflux
	Multi-step reaction with 2 steps 1: propionic acid / 12 h / Reflux; Darkness 2: potassium hydroxide / tetrahydrofuran; methanol; lithium hydroxide monohydrate / 12 h / Reflux
	Multi-step reaction with 2 steps 1: propionic acid / 12 h / 120 °C 2: lithium hydroxide monohydrate; potassium hydroxide / tetrahydrofuran; methanol / 12 h / 120 °C
	Multi-step reaction with 2 steps 1: propionic acid / 12 h / Reflux 2: sodium hydroxide / tetrahydrofuran; methanol / 12 h / Reflux
	Multi-step reaction with 2 steps 1: propionic acid / 10 h / 150 °C / Inert atmosphere 2: potassium hydroxide / tetrahydrofuran; lithium hydroxide monohydrate; methanol / 24 h / 80 °C
	Multi-step reaction with 2 steps 1.1: 80 °C 1.2: 1 h / 140 °C 2.1: hydrogenchloride / trifluoroacetic acid / 36 h / 85 °C
	Multi-step reaction with 2 steps 1: propionic acid / 12 h / Reflux; Darkness 2: potassium hydroxide; methanol; lithium hydroxide monohydrate / tetrahydrofuran / 12 h / Reflux
	Multi-step reaction with 2 steps 1: propionic acid / 12 h / 140 °C / Darkness 2: lithium hydroxide monohydrate; methanol; potassium hydroxide / tetrahydrofuran / 12 h / 80 °C
	Multi-step reaction with 2 steps 1: propionic acid / 12 h / 150 °C 2: potassium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 12 h / 90 °C

Reference： [1]Zhang, Xiaoyuan; Zhu, Biaobiao; Zhou, Li; Liu, Ping; Deng, Wenji [Synthetic Communications, 2015, vol. 45, # 23, p. 2730 - 2739]
[2]Zhao, Xin; Yuan, Lin; Zhang, Zeng-Qi; Wang, Yong-Song; Yu, Qiong; Li, Jun [Inorganic Chemistry, 2016, vol. 55, # 11, p. 5287 - 5296]
[3]Yuan, Shuai; Qin, Jun-Sheng; Zou, Lanfang; Chen, Ying-Pin; Wang, Xuan; Zhang, Qiang; Zhou, Hong-Cai [Journal of the American Chemical Society, 2016, vol. 138, # 20, p. 6636 - 6642]
[4]Chen, Yu-Zhen; Jiang, Hai-Long [Chemistry of Materials, 2016, vol. 28, # 18, p. 6698 - 6704]
[5]Usov; Ahrenholtz; Maza; Stratakes; Epley; Kessinger; Zhu; Morris [Journal of Materials Chemistry A, 2016, vol. 4, # 43, p. 16818 - 16823]
[6]Jiao, Long; Wan, Gang; Zhang, Rui; Zhou, Hua; Yu, Shu-Hong; Jiang, Hai-Long [Angewandte Chemie - International Edition, 2018, vol. 57, # 28, p. 8525 - 8529][Angew. Chem., 2018, vol. 130, # 28, p. 8661 - 8665,5]
[7]Zeng, Jin-Yue; Wang, Xiao-Shuang; Qi, Yong-Dan; Yu, Yun; Zeng, Xuan; Zhang, Xian-Zheng [Angewandte Chemie - International Edition, 2019, vol. 58, # 17, p. 5692 - 5696][Angew. Chem., 2019, vol. 58, # 131, p. 5748 - 5752,5]
[8]Cao, Rong; Fang, Zhi-Bin; Gong, Xue-Qing; Jin, Shengye; Liu, Junxue; Liu, Tian-Fu; Liu, Ting-Ting; Wang, Kecheng; Wu, Xin-Ping; Yin, Qi; Zhou, Hong-Cai [Journal of the American Chemical Society, 2020, vol. 142, # 28, p. 12515 - 12523]
[9]Wang, Xun; Yang, Deren; Yang, Haozhou; Zhou, Yue; Zuo, Shouwei [Angewandte Chemie - International Edition, 2020, vol. 59, # 43, p. 18954 - 18959][Angew. Chem., 2020, vol. 132, # 43, p. 19116 - 19121,6]
[10]Wang, Chenyuan; Xiong, Chuxiao; Li, Zhike; Hu, Liefeng; Wei, Jianshuang; Tian, Jian [Chemical Communications, 2021, vol. 57, # 33, p. 4035 - 4038]
[11]Lin, Chenxiang; Han, Chaozheng; Zhang, Haijiao; Gong, Lei; Gao, Ying; Wang, Hailong; Bian, Yongzhong; Li, Renjie; Jiang, Jianzhuang [Inorganic Chemistry, 2021, vol. 60, # 6, p. 3988 - 3995]
[12]Atia, Alaa A.; Kimura, Masanari [Tetrahedron, 2021, vol. 90]
[13]Alexandrov, Eugeny V.; Fang, Zhi-Bin; Huang, Qian-Qian; Li, Yu-Lin; Liu, Tian-Fu; Proserpio, Davide M.; Qin, Wei-Kang; Si, Duan-Hui; Yin, Qi; Zhang, An-An; Zhang, Yuan [Angewandte Chemie - International Edition, 2022, vol. 61, # 6][Angew. Chem., 2022, vol. 134, # 6]
[14]Dasgupta, Jyotishman; Kundu, Arup; Maji, Tapas Kumar; Rahimi, Faruk Ahamed; Samanta, Debabrata; Verma, Parul [Angewandte Chemie - International Edition, 2022, vol. 61, # 16][Angew. Chem., 2022, vol. 134, # 16]
[15]Jiang, Guangmei; Liu, Xingyan; Jian, Huilong; Lu, Peng; Bai, Jinwu; Zhang, Guizhi; Yun, Wen; Li, Siqi; He, Youzhou [Chinese Chemical Letters, 2022, vol. 33, # 6, p. 3049 - 3052]

51
iron(III) chloride [ No CAS ]
[ 14609-54-2 ]
5,10,15,20-tetrakis(4-HOOC-C₆H₄)porphin iron [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide for 12h; Reflux;	2.1.2 General Procedure of the Synthesis of Metalloporphyrins General procedure: Metalloporphyrins were prepared by refluxing porphyrins (0.33 mmol) with FeCl3, CoCl2, MnCl2, CuCl2, or Zn(OAc)2 (1.82 mmol) in N,N'-dimethylformamide (DMF, 70 mL) for 12 h. DMF was removed by distillation and the metalloporphyrins were precipitated by adding water. The precipitate was dissolved in 0.1 M NaOH solution and recrystallized by adding 1 M HCl solution. Finally, metalloporphyrins were filtered and dried under vacuum.

Reference： [1]Sun, Weizhi; Liu, Yaojie; Zhang, Haibo; Xian, Mo; Liu, Huizhou [Catalysis Letters, 2015, vol. 145, # 11, p. 1991 - 1999]

52
[ 14609-54-2 ]
[ 7646-79-9 ]
cobalt(II) 4,4',4'',4'''-(porphyrin-5,10,15,20-tetrayl)tetrabenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide for 12h; Reflux;	2.1.2 General Procedure of the Synthesis of Metalloporphyrins General procedure: Metalloporphyrins were prepared by refluxing porphyrins (0.33 mmol) with FeCl3, CoCl2, MnCl2, CuCl2, or Zn(OAc)2 (1.82 mmol) in N,N'-dimethylformamide (DMF, 70 mL) for 12 h. DMF was removed by distillation and the metalloporphyrins were precipitated by adding water. The precipitate was dissolved in 0.1 M NaOH solution and recrystallized by adding 1 M HCl solution. Finally, metalloporphyrins were filtered and dried under vacuum.
	In N,N-dimethyl-formamide at 175℃; for 0.0833333h; Microwave irradiation;
0.33 g	In N,N-dimethyl-formamide at 160 - 170℃; Inert atmosphere;

Reference： [1]Sun, Weizhi; Liu, Yaojie; Zhang, Haibo; Xian, Mo; Liu, Huizhou [Catalysis Letters, 2015, vol. 145, # 11, p. 1991 - 1999]
[2]Carrasco, Sergio; Martín-Matute, Belén; Sanz-Marco, Amparo [Organometallics, 2019]
[3]Zhou, Yiwei; Xiao, Yunheng; Zhao, Jian [New Journal of Chemistry, 2020, vol. 44, # 37, p. 16062 - 16068]

53
[ 14609-54-2 ]
manganese(ll) chloride [ No CAS ]
manganase(II)-5,10,15,20-tetra(4-carboxyphenyl)porphine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide for 12h; Reflux;	2.1.2 General Procedure of the Synthesis of Metalloporphyrins General procedure: Metalloporphyrins were prepared by refluxing porphyrins (0.33 mmol) with FeCl3, CoCl2, MnCl2, CuCl2, or Zn(OAc)2 (1.82 mmol) in N,N'-dimethylformamide (DMF, 70 mL) for 12 h. DMF was removed by distillation and the metalloporphyrins were precipitated by adding water. The precipitate was dissolved in 0.1 M NaOH solution and recrystallized by adding 1 M HCl solution. Finally, metalloporphyrins were filtered and dried under vacuum.

Reference： [1]Sun, Weizhi; Liu, Yaojie; Zhang, Haibo; Xian, Mo; Liu, Huizhou [Catalysis Letters, 2015, vol. 145, # 11, p. 1991 - 1999]

54
[ 14609-54-2 ]
copper dichloride [ No CAS ]
5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin copper(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In methanol; acetone for 24h; Inert atmosphere; Reflux;	2.1. Synthesis of copper- meso -tetrakis-(4-carboxyphenyl)porphyrin (Cu-TCPP) The synthesis of ligand meso -tetrakis-(4-carboxyphenyl)- porphyrin (TCPP) was achieved by taking terephthaladehydic acid (0.338 g, 2.25 mmol) and dried pyrrole (0.2 mL, 0.193 g, 2.88 mmol) in two neck round bottom flask containing propionic acid (100 mL). The reaction mixture was refluxed in inert atmosphere (N 2 atmosphere) for two hours. After the completion of the reaction, the mixture was cooled to room temperature and the precipitated product was filtered, washed with cold methanol and dried. Subsequently, the product was recrystallized in 1:1 chloroform-acetone mixture and purple coloured crystals were obtained (12% yield). For the preparation of copper- meso -tetrakis- (4-carboxyphenyl)porphyrin (Cu-TCPP) complex, metal salt cupric chloride was dissolved in 5 mL of dry methanol. Dropwise addition of the dissolved salt was then carried out in to the round bottom flask containing solution of 1 mmol of TCPP in dry acetone (45 mL) under nitrogen atmosphere. The final reaction mixture was refluxed for 24 h under N 2 atmosphere. After reaction comple- tion, the solvent was evaporated and impurities were removed by washing the crude product with methanol and acetone. Finally, the dark green coloured solid product was isolated, (Yield: 86%). [33- 37] ( 1 H NMR, 400 MHz, DMSO-d 6 : (ppm) 8.77 (8H, d, -pyrrole proton), 8.30 (8H, d, o -phenyl), 8.25 (8H, d, m, p -phenyl). ( [13] C NMR, 400 MHz, DMSO-d 6 : (ppm) 167.90 (COOH carbon), 145.91, 134.93, 130.98 (phenyl carbons), 119.82 ( meso carbon), 128.38 (pyrrolic carbon). HR-MS (ESI-MS) Calcd: 851.1203(C 48 H 28 N 4 O 8 Cu).
	In N,N-dimethyl-formamide for 12h; Reflux;	2.1.2 General Procedure of the Synthesis of Metalloporphyrins General procedure: Metalloporphyrins were prepared by refluxing porphyrins (0.33 mmol) with FeCl3, CoCl2, MnCl2, CuCl2, or Zn(OAc)2 (1.82 mmol) in N,N'-dimethylformamide (DMF, 70 mL) for 12 h. DMF was removed by distillation and the metalloporphyrins were precipitated by adding water. The precipitate was dissolved in 0.1 M NaOH solution and recrystallized by adding 1 M HCl solution. Finally, metalloporphyrins were filtered and dried under vacuum.
	In N,N-dimethyl-formamide at 175℃; for 0.0833333h; Microwave irradiation;

Reference： [1]Anjali, Kaiprathu; Ganesh, Venkatachalam; Christopher, Jayaraj; Sakthivel, Ayyamperumal [Journal of Organometallic Chemistry, 2020, vol. 929]
[2]Sun, Weizhi; Liu, Yaojie; Zhang, Haibo; Xian, Mo; Liu, Huizhou [Catalysis Letters, 2015, vol. 145, # 11, p. 1991 - 1999]
[3]Carrasco, Sergio; Martín-Matute, Belén; Sanz-Marco, Amparo [Organometallics, 2019]

55
zinc(II) acetate tetrahydrate [ No CAS ]
[ 14609-54-2 ]
5,10,15,20-tetrakis(4-carboxyphenyl)porphyrinatozinc(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In methanol at 20℃;

Reference： [1]Adineh, Maryam; Tahay, Pooya; Ameri, Mohsen; Safari, Nasser; Mohajerani, Ezeddin [RSC Advances, 2016, vol. 6, # 18, p. 14512 - 14521]

56
[ 10025-69-1 ]
[ 14609-54-2 ]
dichloro‑5,10,15,20‑tetrakis(4‑carboxyphenyl)porphyrinato tin(IV) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.6%	In N,N-dimethyl-formamide at 100℃; for 8h;	5,10,15,20-Tetrakis(4-carboxyphenyl)porphyrininato-Zicn(II), (TCPP-Zn(II)) TCPP-Sn(IV) was synthesizedfollowing a similar previously reported procedure(Manke et al. 2014); TCPP (0.5514 mmol) and SnCl2·2H2O(1.3297 mmol) were mixed in DMF (100 mL); this mixturewas left under stirring for 8 h at 100 °C open to the atmosphere.The TCPP-Sn(IV) was purified by means of columnchromatography using alumina as the stationary phase andpetroleum ether:ethyl acetate (10:1) as the mobile phase(rf = 0.60). Yield 0.263 g (52.6%); melting point > 300 °C;UV-Vis (ethyl acetate) λ (nm): 428, 557, 598.
	With pyridine for 6h; Reflux;
	With pyridine at 120℃;	Synthesis of TCPP and SnTCPP Tetrakis-(4-carboxyphenyl) porphyrin (TCPP) was synthesized according to the way they suggested in a paper [27]. For the synthesis of its tin complex, TCPP was dissolved in 100 mL pyridine, and the resulting solution was refluxed with the SnCl2·2H2O salt at 120 °C. The product obtained was washed with water and dried in an oven at 60 °C.

Reference： [1]Espitia-Almeida, Fabián; Díaz-Uribe, Carlos; Vallejo, William; Peña, Orlando; Gómez-Camargo, Doris; Bohórquez, Arnold R. Romero; Zarate, Ximena; Schott, Eduardo [Chemical Papers, 2021, vol. 75, # 9, p. 4817 - 4829]
[2]Zargari; Rahimi; Yousefi [RSC Advances, 2016, vol. 6, # 29, p. 24218 - 24228]
[3]Yaghoubi-berijani, Marzieh; Bahramian, Bahram; Zargari, Solmaz [Research on Chemical Intermediates, 2020, vol. 46, # 1, p. 197 - 213]

57
[ 6147-53-1 ]
[ 14609-54-2 ]
[5,10,15,20-tetrakis(4-carboxyphenyl)porphyrinato]Co(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In N,N-dimethyl-formamide; at 120℃; for 12h;	A mixture of TPP-COOH (0.26 g, 0.32 mmol) and Co(OAc)2·4H2O (0.608 g, 3.2mmol) was refluxed in N,N-dimethylformamide (DMF, 30 mL) for 12 h at 120 C.After cooled to room temperature, the mixture was rinsed with H2O (150 mL) andthen dried with Na2SO4. The purple solid product was obtained (0.21 g, yield 78%).Anal. Calcd. for [M]: 847.1234; Found: 847.1237 (Fig. S5).

Reference： [1]Journal of Materials Chemistry A,2017,vol. 5,p. 6263 - 6276
[2]Dalton Transactions,2018,vol. 47,p. 8801 - 8806
[3]Chinese Chemical Letters,2022
[4]Journal of Materials Chemistry A,2016,vol. 4,p. 3933 - 3946
[5]New Journal of Chemistry,2018,vol. 42,p. 1715 - 1724
[6]Advanced Functional Materials,2019,vol. 29

58
[ 50446-44-1 ]
[ 10026-11-6 ]
[ 14609-54-2 ]
6Zr⁽⁴⁺⁾*2C₂₇H₁₅O₆^(3-)*6O^(2-)*3O₂*C₄₈H₂₄N₄O₈^(6-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6636 - 6642

59
[ 14609-54-2 ]
5,10,15,20-tetrakis(4'-carboxamidophenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With thionyl chloride for 1h; Reflux;	2.4. Synthesis of tetra- and octaamide porphyrins (1 and 2) General procedure: Tetraacid (0.35 g, 0.443 mmol) or octaacid (0.428 g, 0.443 mmol)was taken in a 50 mL RB flask. To this, distilled SOCl2 (2 mL,0.0274 mol) was added dropwise and refluxed for 1 h. Then excessamount of SOCl2 was removed by vacuum distillation. To this, coldNH4OH (6 mL) was added slowly till the precipitate was formed.The precipitate was filtered and washed with water (50 mL 3).The crude porphyrins were recrystallized from CH3OH and acetonemixture (2:8, v/v). Yield was found to be 98% (0.34 g, 0.432 mmol)for 1 and 97% (0.411 g, 0.428 mmol) for 2. 1: UV/Vis (DMSO): λmax (nm) (ε x 103 L mol-1 cm-1) 417(513),515(23.9), 549(5.01), 590(1.66), 647(1.58). 1H NMR in DMSO-d6:δ (ppm) 8.82 (s, 8H, b-pyrrole-H), 8.33 (s, 4H, O-H of imidol), 8.28(s, 16H, meso-phenyl-H), 7.63 (s, 4H, N-H of imidol), 2.98 (s, 2H,N-H). ESI-MS (m/z): found 787.837 [M+H]+, calcd. 787.843. Anal.calcd. for C48H34N8O4: C, 73.27; H, 4.36; N, 14.24%. Found: C, 73.40;H, 4.58; N, 14.17%.

Reference： [1]Yadav, Pinky; Sankar, Muniappan [Dyes and Pigments, 2017, vol. 139, p. 651 - 657]

60
manganese(II) nitrate hydrate [ No CAS ]
[ 64-17-5 ]
[ 14609-54-2 ]
[ 33513-42-7 ]
C₄₈H₂₄N₄O₈^(6-)*3Mn⁽²⁺⁾*4H₂O*(x)C₃H₇NO*(y)C₂H₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,2,4,5-benzenetetracarboxylic acid at 100℃; for 72h; High pressure;	2.2. Synthesis of [Mn3(TCPP)(H2O)4]·nD (1) and [Mn(H4TCPP)(H2O)2]·nD (2) All solvents and chemicals were used as received from reliable commercial sources. The non-metallated meso-tetra(4-carboxyphenyl)porphyrin, manganese(II) nitrate hydrate 99.99%, 1,2,4,5-benzenetetracarboxylic acid (bta) and the solvents N,N-dimethylformamide 99.8% (DMF) and ethanol 96% were purchased from Sigma-Aldrich Co. (0008) meso-tetra(4-carboxyphenyl)porphyrin (7.9mg, 0.01mmol), manganese(II) nitrate hydrate 99.99% (17.6mg, 0.1mmol) and 1,2,4,5-benzenetetracarboxylic acid (25.2mg, 0.1mmol), as crystallization helper (crystals were not obtained without bta used in the synthesis), were dissolved in a mixture of DMF (3mL) and ethanol (1mL) in a small capped vial, sonicated to ensure homogeneity and heated to 100°C for 72h, yielding prismatic and brown crystals of compound 1, washed thoroughly with ethanol and dried in air at room temperature. νmax/cm-1: 3390, (C(sp2)H), 3070 (OH), 1700 (CO). 1600-1400 (CC), 1320 (CO), 1300 (CN), 1000 (MnTCPP). (Fig. S1, Supplementary information). For compound 2 we just had to let fresh synthesized crystals in mother liquid, at ambient conditions (20°C, 1atm). However color and shape of crystals dont change what made difficult distinguish each compound to the naked eye and proportions of each compound.

Reference： [1]Amayuelas, Eder; Fidalgo-Marijuan, Arkaitz; Bazán, Begoña; Urtiaga, Miren Karmele; Barandika, Gotzone; Lezama, Luis; Arriortua, María Isabel [Journal of Solid State Chemistry, 2017, vol. 247, p. 161 - 167]

61
3,5-didodecylaniline [ No CAS ]
[ 14609-54-2 ]
C₁₆₈H₂₄₂N₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Stage #2: 3,5-didodecylaniline In chloroform at 20℃; for 24h; Inert atmosphere; Alkaline conditions;

Reference： [1]van der Weegen, Rob; Teunissen, Abraham J. P.; Meijer [Chemistry - A European Journal, 2017, vol. 23, # 15, p. 3773 - 3783]

62
3,5-bis[(S)-3,7-dimethyloctyloxy]aniline [ No CAS ]
[ 14609-54-2 ]
C₁₅₂H₂₁₀N₈O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Stage #2: 3,5-bis[(S)-3,7-dimethyloctyloxy]aniline In chloroform at 20℃; for 24h; Inert atmosphere; Alkaline conditions;

Reference： [1]van der Weegen, Rob; Teunissen, Abraham J. P.; Meijer [Chemistry - A European Journal, 2017, vol. 23, # 15, p. 3773 - 3783]

63
[ 885111-15-9 ]
[ 14609-54-2 ]
C₂₁₆H₃₃₈N₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Stage #2: 3,4,5-tridodecyl aminobenzene In chloroform at 20℃; for 24h; Inert atmosphere; Alkaline conditions;

Reference： [1]van der Weegen, Rob; Teunissen, Abraham J. P.; Meijer [Chemistry - A European Journal, 2017, vol. 23, # 15, p. 3773 - 3783]

64
[ 17612-91-8 ]
[ 14609-54-2 ]
C₆₄H₅₈N₈O₈S₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one	1 The monomer 1, with its protected thiol groups, was obtained beforehand from the free base 5,10,15,20-tetra(4-carboxyphenyl)porphyrin, by reacting, as shown in FIG. 4, this porphyrin with S-acetylcysteamine hydrochloride in the presence of benzotriazol-1-yl-oxy-tripyrrolidinophosphonium hexafluorophosphate (PyBOP) and of N-ethyl-N,N-diisopropylamine (DIEA) in N-methyl-2-pyrrolidone (NMP), under standard conditions. The S-acetylcysteamine hydrochloride was itself obtained beforehand by reaction between cysteamine and acetyl chloride

Reference： [1]Current Patent Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES - US9597677, 2017, B2 Location in patent: Page/Page column 12

65
[ 14609-54-2 ]
[ 55216-11-0 ]
C₄₈H₃₀N₄O₈*C₆₃H₁₁₂O₃₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In neat (no solvent) for 0.333333h;

Reference： [1]Ikeda, Atsushi; Satake, Shuhei; Mae, Tomoya; Ueda, Masafumi; Sugikawa, Kouta; Shigeto, Hajime; Funabashi, Hisakage; Kuroda, Akio [ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 555 - 559]

66
(S)-tert-butyl 2-(2-amino-4-tert-butoxy-4-oxobutanoyl)hydrazinecarboxylate [ No CAS ]
[ 14609-54-2 ]
tert-butyl 3-[4-(7,12-bis{4-[(-3-(tert-butoxy)-1-{N′-[(tert-butoxy)carbonyl]hydrazinecarbonyl}-3-oxopropyl)-carbamoyl]phenyl}-17-{4-[(3-(tert-butoxy)-1-{N′-[(tertbutoxy)carbonyl]hydrazinecarbonyl}-3-oxopropyl)carbamoyl]-phenyl}-21,22,23,24-tetraazapentacyclo[16.2.1.13,6.18,11.113,16]-tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-2-yl)phenyl]formamido}-3-{N′-[(tert-butoxy)carbonyl]hydrazinecarbonyl}propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 18h; Inert atmosphere;

Reference： [1]Hewitt, Sarah H.; Wilson, Andrew J. [European Journal of Organic Chemistry, 2018, vol. 2018, # 16, p. 1872 - 1879]

67
[ 17114-97-5 ]
[ 14609-54-2 ]
C₈₀H₉₀N₈O₁₆ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 1872 - 1879

68
[ 201002-47-3 ]
[ 14609-54-2 ]
Fmoc-D-Lys-Por [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		General procedure: A 20 mL glass vial was charged with mTCPP (0.08 g, 0.1 mmol) and dissolved in 1 mL ofanhydrous dimethylformamide (DMF), and the suspension was sonicated. To this suspension, a DMFsolution of HBTU (0.152 g, 0.4 mmol) was added dropwise, followed by an addition of 5% DIPEA.The resulting solution was sonicated for 1 h at room temperature. Then, DMF solution containingFmoc-D-Lys-OH.HCl (0.324 g, 0.8 mmol or Fmoc-Lys-OH (0.294, 0.8 mmol) was added dropwise to theabove reaction mixture, and sonication was continued for another 45 min. The resulting mixture wasneutralized with 10% citric acid and the crude compound was collected. The compound was purified using silica column with methylene chloride/methanol/30% NH4OH (70:15:2.5, v/v) as a mobilephase. After evaporating the solvent, a dark violet Fmoc-protected compound was obtained whichwas dried in vacuum. The obtained yields were 52% (0.1131 g) and 55% (0.12 g) for Fmoc-D-Lys-Porand Fmoc-L-Lys-Por, respectively. NMR data: Fmoc-D-Lys-Por: 1H-NMR (500 MHz, d6-DMSO): -delta -3.03 (br, s, 2H, NH-pyrrole),1.18-1.83 (m, 24H, gammaLys, deltaLys, betaLys), 3.29-3.75 (m, 8H, epsilonLys), 3.86-4.19 (m, 4H, CH-Fmoc), 4.20-4.33(m, 12H, CH2-Fmoc and alphaLys), 7.07 (s, 4H, -CH-NH-COO-, amide), 7.26-7.39 (M, 16H, Ar), 7.67-7.89(m, 16H, Ar), 8.15-8.29 (m, 16H, Ar), 8.69 (s, 8H, Ar), 8.87 (s, 4H, -CO-NH-CH2-, amide). 13C-NMR(75 MHz, dmso): delta 174.10, 166.04, 155.63, 143.92, 143.75, 143.54, 143.48, 142.56, 140.58, 139.36,137.38, 134.17, 133.93, 128.90, 127.47, 127.26, 126.96, 125.78, 125.19, 121.35, 119.98, 119.29, 109.74,65.49, 55.01, 46.81, 31.45, 28.83, 22.94, 22.68. HR-MS (ESI): m/z 1096.4487 (calculated for [M + H]2+1096.4365). Fmoc-L-Lys-Por: 1H-NMR (500 MHz, d6-DMSO): -delta -3.02 (br, s, 2H, NH-pyrrole),1.18-1.82 (m, 24H, gammaLys, deltaLys, betaLys), 3.29-3.42 (m, 8H, epsilonLys), 3.73-3.84 (m, 4H, CH-Fmoc), 4.19-4.34(m, 12H, CH2-Fmoc and alphaLys), 7.01 (s, 4H, -CH-NH-COO-, amide), 7.26-7.29 (M, 16H, Ar), 7.67-7.86(m, 16H, Ar), 8.17-8.43 (m, 16H, Ar), 8.70 (s, 8H, Ar), 8.87 (s, 4H, -CO-NH-CH2-, amide). 13C-NMR(75 MHz, dmso): delta 174.15, 166.05, 155.57, 143.94, 143.77, 143.56, 143.12, 142.53, 140.59, 139.34, 137.38,134.22, 133.97, 128.89, 127.48, 127.26, 126.97, 125.77, 125.19, 121.31, 119.95, 119.30, 109.73, 65.40, 55.14,46.71, 31.74, 29.07, 22.91, 22.53. HR-MS (ESI): m/z 1096.45251 (calculated for [M + H]2+ 1096.4365).

Reference： [1]Molecules,2018,vol. 23

69
[ 105047-45-8 ]
[ 14609-54-2 ]
Fmoc-L-Lys-Por [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: tetrakis(4-carboxyphenyl)porphyrin With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Sonication; Stage #2: Fmoc-Lys-OH In N,N-dimethyl-formamide for 0.75h; Sonication;	General procedure for the synthesis of lysine-conjugated photosensitizers: Fmoc-D-Lys-Por and Fmoc-L-Lys-Por: General procedure: A 20 mL glass vial was charged with mTCPP (0.08 g, 0.1 mmol) and dissolved in 1 mL ofanhydrous dimethylformamide (DMF), and the suspension was sonicated. To this suspension, a DMFsolution of HBTU (0.152 g, 0.4 mmol) was added dropwise, followed by an addition of 5% DIPEA.The resulting solution was sonicated for 1 h at room temperature. Then, DMF solution containingFmoc-D-Lys-OH.HCl (0.324 g, 0.8 mmol or Fmoc-Lys-OH (0.294, 0.8 mmol) was added dropwise to theabove reaction mixture, and sonication was continued for another 45 min. The resulting mixture wasneutralized with 10% citric acid and the crude compound was collected. The compound was purified using silica column with methylene chloride/methanol/30% NH4OH (70:15:2.5, v/v) as a mobilephase. After evaporating the solvent, a dark violet Fmoc-protected compound was obtained whichwas dried in vacuum. The obtained yields were 52% (0.1131 g) and 55% (0.12 g) for Fmoc-D-Lys-Porand Fmoc-L-Lys-Por, respectively. NMR data: Fmoc-D-Lys-Por: 1H-NMR (500 MHz, d6-DMSO): -δ -3.03 (br, s, 2H, NH-pyrrole),1.18-1.83 (m, 24H, γLys, δLys, βLys), 3.29-3.75 (m, 8H, εLys), 3.86-4.19 (m, 4H, CH-Fmoc), 4.20-4.33(m, 12H, CH2-Fmoc and αLys), 7.07 (s, 4H, -CH-NH-COO-, amide), 7.26-7.39 (M, 16H, Ar), 7.67-7.89(m, 16H, Ar), 8.15-8.29 (m, 16H, Ar), 8.69 (s, 8H, Ar), 8.87 (s, 4H, -CO-NH-CH2-, amide). 13C-NMR(75 MHz, dmso): δ 174.10, 166.04, 155.63, 143.92, 143.75, 143.54, 143.48, 142.56, 140.58, 139.36,137.38, 134.17, 133.93, 128.90, 127.47, 127.26, 126.96, 125.78, 125.19, 121.35, 119.98, 119.29, 109.74,65.49, 55.01, 46.81, 31.45, 28.83, 22.94, 22.68. HR-MS (ESI): m/z 1096.4487 (calculated for [M + H]2+1096.4365). Fmoc-L-Lys-Por: 1H-NMR (500 MHz, d6-DMSO): -δ -3.02 (br, s, 2H, NH-pyrrole),1.18-1.82 (m, 24H, γLys, δLys, βLys), 3.29-3.42 (m, 8H, εLys), 3.73-3.84 (m, 4H, CH-Fmoc), 4.19-4.34(m, 12H, CH2-Fmoc and αLys), 7.01 (s, 4H, -CH-NH-COO-, amide), 7.26-7.29 (M, 16H, Ar), 7.67-7.86(m, 16H, Ar), 8.17-8.43 (m, 16H, Ar), 8.70 (s, 8H, Ar), 8.87 (s, 4H, -CO-NH-CH2-, amide). 13C-NMR(75 MHz, dmso): δ 174.15, 166.05, 155.57, 143.94, 143.77, 143.56, 143.12, 142.53, 140.59, 139.34, 137.38,134.22, 133.97, 128.89, 127.48, 127.26, 126.97, 125.77, 125.19, 121.31, 119.95, 119.30, 109.73, 65.40, 55.14,46.71, 31.74, 29.07, 22.91, 22.53. HR-MS (ESI): m/z 1096.45251 (calculated for [M + H]2+ 1096.4365).

Reference： [1]Chitgupi, Upendra; Lovell, Jonathan F.; Rajendiran, Venugopal [Molecules, 2018, vol. 23, # 4]

70
[ 1633-05-2 ]
[ 14609-54-2 ]
[ 33513-42-7 ]
2C₄₈H₂₆N₄O₈^(4-)*4Sr⁽²⁺⁾*8C₃H₇NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With hydrogenchloride In water at 100℃; for 72.5h; Autoclave; High pressure;	2.2 Synthesis of [Sr₄(TCPP)₂(DMF)₈]_n (1) H4TCPP (0.020g, 0.025mmol) and SrCO3 (0.008g, 0.05mmol) were dissolved in 5mL DMF and 0.5mL 3M HCl and stirred for 30min. Then the mixture was sealed in a 25mL Teflon-lined stainless steel reactor, which was put into an oven at 100°C and left undisturbed for 3days. Subsequently, after being cooled to room temperature, purple cuboid-shaped crystals suitable for X-ray diffraction analysis were obtained by filtration with the yield of 0.019g, 61% (based on L ligand). Anal. calcd for C30H27SrN4O6: C 57.45, H 4.34, N 8.93. Found: C 57.39, H 4.38, N 8.85. IR/cm-1 (KBr): 1658, 1591, 1541, 1392, 1095, 964, 835, 727.

Reference： [1]Hou, Yuxia; Liu, Lu; Zhang, Zuhong; Sun, Junshan; Zhang, Yuping; Jiang, Jianzhuang [Inorganic Chemistry Communications, 2018, vol. 95, p. 36 - 39]

71
[ 14609-54-2 ]
[ 33513-42-7 ]
barium(II) chloride [ No CAS ]
2C₄₈H₂₆N₄O₈^(4-)*4Ba⁽²⁺⁾*8C₃H₇NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With hydrogenchloride In water at 120℃; for 72.5h; Autoclave; High pressure;	2.3 Synthesis of [Ba₄(TCPP)₂(DMF)₈]_n (2) The mixture of BaCl2 (0.021g, 0.1mmol), H4TCPP (0.034g, 0.05mmol), DMF(5mL), and 3M HCl (1mL) was magnetic stirred for 30min, which was then sealed in 25mL Teflon-lined stainless steel autoclave. Then the autoclave was heated to 120°C in an oven and left undisturbed for 3days. Purple slice-shaped crystals suitable for X-ray diffraction analysis were obtained by filtration with the yield of 0.036g, 54%. Anal. calcd for C30H27BaN4O6: C 53.23, H 4.02, N 8.27. Found: C 53.19, H 4.13, N 8.21. IR/cm-1 (KBr): 1660, 1585, 1541, 1402, 1099, 968, 840, 783.

Reference： [1]Hou, Yuxia; Liu, Lu; Zhang, Zuhong; Sun, Junshan; Zhang, Yuping; Jiang, Jianzhuang [Inorganic Chemistry Communications, 2018, vol. 95, p. 36 - 39]

72
[ 14609-54-2 ]
[ 62-53-3 ]
C₇₂H₅₀N₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 48h;	General Procedure for Synthesis of New Porphyrin Derivatives a-f General procedure: A 25 mL round bottom flask was equipped with TCPP(100 mg, 0.126 mmol), DCC (120 mg, 0.57 mmol) andDIPEA (80 mg, 62 mmol) dissolved in THF. The whole mixturewas stirred on magnetic stirrer at room temperaturefollowed by addition of corresponding amine or hydrazide.TLC technique was used to monitor the progress of reaction.The stirring of reaction mixture was allowed until thecompletion of reaction i.e. up to 48 h. After that, the reactionmixture was extracted in ethyl acetate followed bytreatment of saturated NaHCO3 and diluted HCl solutionto expel out unreacted quantity of TCPP and amine or hydrazide,respectively. The ethyl acetate layer was dried overFig. 1 Representative structure of TCPP anhydrous Na2SO4 and evaporated to yield dark brown coloredcorresponding new porphyrin derivatives shown inFig. 2a-f. The synthetic route for proposed new porphyrinderivatives illustrates in Scheme 1. The spectral purity andformation of compounds were confirmed by analytical techniquesviz. IR, 1H NMR and mass analysis

Reference： [1]Mahajan, Prasad G.; Dige, Nilam C.; Vanjare, Balasaheb D.; Phull, Abdul Rehman; Kim, Song Ja; Hong, Seong-Karp; Lee, Ki Hwan [Journal of Fluorescence, 2018, vol. 28, # 4, p. 871 - 882]

73
[ 141-43-5 ]
[ 14609-54-2 ]
C₅₆H₅₀N₈O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 48h;	General Procedure for Synthesis of New Porphyrin Derivatives a-f General procedure: A 25 mL round bottom flask was equipped with TCPP(100 mg, 0.126 mmol), DCC (120 mg, 0.57 mmol) andDIPEA (80 mg, 62 mmol) dissolved in THF. The whole mixturewas stirred on magnetic stirrer at room temperaturefollowed by addition of corresponding amine or hydrazide.TLC technique was used to monitor the progress of reaction.The stirring of reaction mixture was allowed until thecompletion of reaction i.e. up to 48 h. After that, the reactionmixture was extracted in ethyl acetate followed bytreatment of saturated NaHCO3 and diluted HCl solutionto expel out unreacted quantity of TCPP and amine or hydrazide,respectively. The ethyl acetate layer was dried overFig. 1 Representative structure of TCPP anhydrous Na2SO4 and evaporated to yield dark brown coloredcorresponding new porphyrin derivatives shown inFig. 2a-f. The synthetic route for proposed new porphyrinderivatives illustrates in Scheme 1. The spectral purity andformation of compounds were confirmed by analytical techniquesviz. IR, 1H NMR and mass analysis

Reference： [1]Mahajan, Prasad G.; Dige, Nilam C.; Vanjare, Balasaheb D.; Phull, Abdul Rehman; Kim, Song Ja; Hong, Seong-Karp; Lee, Ki Hwan [Journal of Fluorescence, 2018, vol. 28, # 4, p. 871 - 882]

74
[ 504-29-0 ]
[ 14609-54-2 ]
C₆₈H₄₆N₁₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 48h;	General Procedure for Synthesis of New Porphyrin Derivatives a-f General procedure: A 25 mL round bottom flask was equipped with TCPP(100 mg, 0.126 mmol), DCC (120 mg, 0.57 mmol) andDIPEA (80 mg, 62 mmol) dissolved in THF. The whole mixturewas stirred on magnetic stirrer at room temperaturefollowed by addition of corresponding amine or hydrazide.TLC technique was used to monitor the progress of reaction.The stirring of reaction mixture was allowed until thecompletion of reaction i.e. up to 48 h. After that, the reactionmixture was extracted in ethyl acetate followed bytreatment of saturated NaHCO3 and diluted HCl solutionto expel out unreacted quantity of TCPP and amine or hydrazide,respectively. The ethyl acetate layer was dried overFig. 1 Representative structure of TCPP anhydrous Na2SO4 and evaporated to yield dark brown coloredcorresponding new porphyrin derivatives shown inFig. 2a-f. The synthetic route for proposed new porphyrinderivatives illustrates in Scheme 1. The spectral purity andformation of compounds were confirmed by analytical techniquesviz. IR, 1H NMR and mass analysis

Reference： [1]Mahajan, Prasad G.; Dige, Nilam C.; Vanjare, Balasaheb D.; Phull, Abdul Rehman; Kim, Song Ja; Hong, Seong-Karp; Lee, Ki Hwan [Journal of Fluorescence, 2018, vol. 28, # 4, p. 871 - 882]

75
[ 613-94-5 ]
[ 14609-54-2 ]
C₇₆H₅₄N₁₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 48h;	General Procedure for Synthesis of New Porphyrin Derivatives a-f General procedure: A 25 mL round bottom flask was equipped with TCPP(100 mg, 0.126 mmol), DCC (120 mg, 0.57 mmol) andDIPEA (80 mg, 62 mmol) dissolved in THF. The whole mixturewas stirred on magnetic stirrer at room temperaturefollowed by addition of corresponding amine or hydrazide.TLC technique was used to monitor the progress of reaction.The stirring of reaction mixture was allowed until thecompletion of reaction i.e. up to 48 h. After that, the reactionmixture was extracted in ethyl acetate followed bytreatment of saturated NaHCO3 and diluted HCl solutionto expel out unreacted quantity of TCPP and amine or hydrazide,respectively. The ethyl acetate layer was dried overFig. 1 Representative structure of TCPP anhydrous Na2SO4 and evaporated to yield dark brown coloredcorresponding new porphyrin derivatives shown inFig. 2a-f. The synthetic route for proposed new porphyrinderivatives illustrates in Scheme 1. The spectral purity andformation of compounds were confirmed by analytical techniquesviz. IR, 1H NMR and mass analysis

Reference： [1]Mahajan, Prasad G.; Dige, Nilam C.; Vanjare, Balasaheb D.; Phull, Abdul Rehman; Kim, Song Ja; Hong, Seong-Karp; Lee, Ki Hwan [Journal of Fluorescence, 2018, vol. 28, # 4, p. 871 - 882]

76
[ 1068-57-1 ]
[ 14609-54-2 ]
C₅₆H₄₆N₁₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 48h;	General Procedure for Synthesis of New Porphyrin Derivatives a-f General procedure: A 25 mL round bottom flask was equipped with TCPP(100 mg, 0.126 mmol), DCC (120 mg, 0.57 mmol) andDIPEA (80 mg, 62 mmol) dissolved in THF. The whole mixturewas stirred on magnetic stirrer at room temperaturefollowed by addition of corresponding amine or hydrazide.TLC technique was used to monitor the progress of reaction.The stirring of reaction mixture was allowed until thecompletion of reaction i.e. up to 48 h. After that, the reactionmixture was extracted in ethyl acetate followed bytreatment of saturated NaHCO3 and diluted HCl solutionto expel out unreacted quantity of TCPP and amine or hydrazide,respectively. The ethyl acetate layer was dried overFig. 1 Representative structure of TCPP anhydrous Na2SO4 and evaporated to yield dark brown coloredcorresponding new porphyrin derivatives shown inFig. 2a-f. The synthetic route for proposed new porphyrinderivatives illustrates in Scheme 1. The spectral purity andformation of compounds were confirmed by analytical techniquesviz. IR, 1H NMR and mass analysis

Reference： [1]Mahajan, Prasad G.; Dige, Nilam C.; Vanjare, Balasaheb D.; Phull, Abdul Rehman; Kim, Song Ja; Hong, Seong-Karp; Lee, Ki Hwan [Journal of Fluorescence, 2018, vol. 28, # 4, p. 871 - 882]

77
[ 30065-27-1 ]
[ 14609-54-2 ]
C₈₄H₆₂N₂₀O₈S₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 48.0h;	General procedure: A 25 mL round bottom flask was equipped with TCPP(100 mg, 0.126 mmol), DCC (120 mg, 0.57 mmol) andDIPEA (80 mg, 62 mmol) dissolved in THF. The whole mixturewas stirred on magnetic stirrer at room temperaturefollowed by addition of corresponding amine or hydrazide.TLC technique was used to monitor the progress of reaction.The stirring of reaction mixture was allowed until thecompletion of reaction i.e. up to 48 h. After that, the reactionmixture was extracted in ethyl acetate followed bytreatment of saturated NaHCO3 and diluted HCl solutionto expel out unreacted quantity of TCPP and amine or hydrazide,respectively. The ethyl acetate layer was dried overFig. 1 Representative structure of TCPP anhydrous Na2SO4 and evaporated to yield dark brown coloredcorresponding new porphyrin derivatives shown inFig. 2a-f. The synthetic route for proposed new porphyrinderivatives illustrates in Scheme 1. The spectral purity andformation of compounds were confirmed by analytical techniquesviz. IR, 1H NMR and mass analysis

Reference： [1]Journal of Fluorescence,2018,vol. 28,p. 871 - 882

78
[ 14609-54-2 ]
iron(II) chloride [ No CAS ]
iron(III) meso-tetra(4-carboxyphenyl)porphine chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide at 150℃; for 1h;	2.3 General Procedure of the Synthesisof Metalloporphyrins (Scheme 2) General procedure: Metalloporphyrins were synthesized according to aknown procedure described in the literature. Porphyrins(0.33 mmol) were dissolved in 100 mL of dimethylformamide(DMF), FeCl2,CoCl2,or MnCl2(1.9 mmol) was addedand the reaction was refluxed for 1 h at 150 °C. The reactionmixture was cooled to room temperature and quenched with6 M HCl solution (40 mL). The precipitate was filtered andwashed with 3 M HCl solution and then dried under vacuum.

Reference： [1]Yu, Zongjiang; Zhai, Guoqing; Xian, Mo; Lu, Ming; Wang, Pengcheng; Jiang, Tao; Xu, Chao; Sun, Weizhi [Catalysis Letters, 2018, vol. 148, # 9, p. 2636 - 2642]

79
[ 109-97-7 ]
[ 623-27-8 ]
[ 14609-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	In propionic acid for 0.833333h; Reflux; Inert atmosphere;	2.2 General Procedure of the Synthesisof Porphyrins (Scheme 1) General procedure: Porphyrins were synthesized by the modified typicalAdler reaction. The benzaldehyde or substituted benzaldehyde(40 mmol) was heated to reflux with propionic acid(300 mL), and pyrrole (40 mmol) was added drop-wise for30 min under N2atmosphere. The reaction continued toreflux for 20 min. The temperature was brought to 90 °C andthe dark precipitates were filtered. The residue was washedwith hot DCM (35 °C) and deionized water and dried undervacuum to obtain the crystal of porphyrins.

Reference： [1]Yu, Zongjiang; Zhai, Guoqing; Xian, Mo; Lu, Ming; Wang, Pengcheng; Jiang, Tao; Xu, Chao; Sun, Weizhi [Catalysis Letters, 2018, vol. 148, # 9, p. 2636 - 2642]

80
copper(II) nitrate [ No CAS ]
[ 14609-54-2 ]
C₄₈H₃₀N₄O₈*2Cu⁽²⁺⁾*4NO₃^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With polyvinylpyrrolidone (PVP) In N,N-dimethyl-formamide at 80℃; for 24h;

Reference： [1]Li, Bo; Wang, Xiaoya; Chen, Lei; Zhou, Yanling; Dang, Wentao; Chang, Jiang; Wu, Chengtie [Theranostics, 2018, vol. 8, # 15, p. 4086 - 4096]

81
[ 5970-45-6 ]
[ 14609-54-2 ]
zinc 5,10,15,20-tetrakis (4-carboxyphenyl)porphyrin tetrasodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: zinc(II) acetate dihydrate; tetrakis(4-carboxyphenyl)porphyrin In N,N-dimethyl-formamide for 0.75h; Reflux; Stage #2: With sodium hydroxide In N,N-dimethyl-formamide

Reference： [1]Chakraborty, Ritobrita; Sahoo, Sumit; Halder, Nyancy; Rath, Harapriya; Chattopadhyay, Krishnananda [ACS Chemical Neuroscience, 2019, vol. 10, # 1, p. 573 - 587]

82
iron(III) chloride [ No CAS ]
[ 14609-54-2 ]
4,4′,4″,4‴-(iron(III)porphine-5,10,15,20-tetrayl)-tetrakis(benzoic acid) chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide at 150℃; for 2h;	General procedure: Metalloporphyrins (MTCPPs) were prepared by refluxing TCPP with metal sources (copper(II) chloride dihydrate, zinc(II) acetate dihydrate, iron(III) chloride, manganese(II) acetate) in dimethylformamide (DMF) at 150°C for 2 h. DMF was removed, and MTCPPs were precipitated by adding water. The precipitate was dissolved in NaOH solution and reprecipitated by adding HCl solution. MTCPP were obtained after dissolved in ethanol and evaporated [6].

Reference： [1]Chanhom, Padtaraporn; Charoenlap, Nisanart; Manipuntee, Chonnavee; Insin, Numpon [Journal of Magnetism and Magnetic Materials, 2019, vol. 475, p. 602 - 610]

83
copper(II) choride dihydrate [ No CAS ]
[ 14609-54-2 ]
5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin copper(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide at 150℃; for 2h;	General procedure: Metalloporphyrins (MTCPPs) were prepared by refluxing TCPP with metal sources (copper(II) chloride dihydrate, zinc(II) acetate dihydrate, iron(III) chloride, manganese(II) acetate) in dimethylformamide (DMF) at 150°C for 2 h. DMF was removed, and MTCPPs were precipitated by adding water. The precipitate was dissolved in NaOH solution and reprecipitated by adding HCl solution. MTCPP were obtained after dissolved in ethanol and evaporated [6].
	In N,N-dimethyl-formamide for 6h; Reflux;
	In N,N-dimethyl-formamide for 6h; Reflux;

Reference： [1]Chanhom, Padtaraporn; Charoenlap, Nisanart; Manipuntee, Chonnavee; Insin, Numpon [Journal of Magnetism and Magnetic Materials, 2019, vol. 475, p. 602 - 610]
[2]Ding, Yong; Dong, Congzhao; Dong, Yinjuan; Hu, Qiyu; Ma, Baochun; Sun, Wanjun; Xu, Chunjiang [Journal of Materials Chemistry A, 2020, vol. 8, # 7, p. 4062 - 4072]
[3]Elsner, Martin; Fischer, Roland A.; Hou, Shujin; Li, Weijin; Mukherjee, Soumya; Zhou, Zhenyu [Angewandte Chemie - International Edition, 2021, vol. 60, # 37, p. 20551 - 20557][Angew. Chem., 2021, vol. 133, # 37, p. 20714 - 20721]

84
[ 5970-45-6 ]
[ 14609-54-2 ]
5,10,15,20-tetrakis(4-carboxyphenyl)porphyrinatozinc(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	In water for 0.5h; Sonication;	4.4. General Synthesis of Metalloporphyrins under Ultrasound A mixture of the porphyrin (50 mg), the metal salt (1 equivalent) and 1 mL of wateror NaOH (2 M) aqueous solution were placed in a glass container (microwave reactorglass vial-10 mL) and placed into the ultrasound bath (Bandelin Sonorex RK100H) ensuringthat all the reaction solution is below the level of the water at the ultrasound bath(ca. 1 cm depth). The reaction was followed by UV-Vis at each 10 min. Once complete, thereaction was neutralized with HCl (1 M) solution. The hydrophobic porphyrins werepurified through liquid-liquid extraction using ethyl acetate, the organic phase was driedwith Na2SO4 anhydride and the solvent removed through evaporation. Water-solubleporphyrins were purified through exclusion chromatography (Sephadex G-10) usingwater as eluent, followed by water evaporation.
	In N,N-dimethyl-formamide at 150℃; for 2h;	General procedure: Metalloporphyrins (MTCPPs) were prepared by refluxing TCPP with metal sources (copper(II) chloride dihydrate, zinc(II) acetate dihydrate, iron(III) chloride, manganese(II) acetate) in dimethylformamide (DMF) at 150°C for 2 h. DMF was removed, and MTCPPs were precipitated by adding water. The precipitate was dissolved in NaOH solution and reprecipitated by adding HCl solution. MTCPP were obtained after dissolved in ethanol and evaporated [6].
	In N,N-dimethyl-formamide for 4h; Reflux;

	In methanol; dichloromethane at 65℃; for 2h; Darkness;	General Procedure for Zn Porphyrin Synthesis Zn-5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin (Zn-TCA4PP): 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin (50 mg, 0.074 mmol) was reacted with an excess of Zn(OAc)2·2H2O (15 mg, 0.11 mmol) in CH2Cl2:CH3OH (20 mL, 10:1) at 65 °C for 2 h in a dark environment. The reaction mixture was rinsed with Milli-Q. The product was purified by silica gel column chromatography with CHCl3:(CH2)4O (20:1) as mobile phase. Purity was confirmed with TLC, 1H NMR, and MALDI-TOF mass spectrometry.
	Stage #1: zinc(II) acetate dihydrate; tetrakis(4-carboxyphenyl)porphyrin In N,N-dimethyl-formamide at 100℃; for 48h; Stage #2: With potassium hydroxide In tetrahydrofuran; methanol; water for 12h; Reflux;

Reference： [1]Gomes, Carla; Peixoto, Mariana; Pineiro, Marta [Molecules, 2021, vol. 26, # 21]
[2]Chanhom, Padtaraporn; Charoenlap, Nisanart; Manipuntee, Chonnavee; Insin, Numpon [Journal of Magnetism and Magnetic Materials, 2019, vol. 475, p. 602 - 610]
[3]Zhang, Liwen; Shi, Xiaobing; Zhang, Zhiheng; Kuchel, Rhiannon P; Namivandi-Zangeneh, Rashin; Corrigan, Nathaniel; Jung, Kenward; Liang, Kang; Boyer, Cyrille [Angewandte Chemie - International Edition, 2021, vol. 60, # 10, p. 5489 - 5496][Angew. Chem., 2021, vol. 133, # 10, p. 5549 - 5556,8]
[4]Gillen, Jonathan H.; Kaushal, Meesha; Kwiatkowski, Carly O.; Middleton, Camilla; Shibu, Abhishek; Walter, Michael G. [Molecules, 2022, vol. 27, # 1]
[5]Alexandrov, Eugeny V.; Fang, Zhi-Bin; Huang, Qian-Qian; Li, Yu-Lin; Liu, Tian-Fu; Proserpio, Davide M.; Qin, Wei-Kang; Si, Duan-Hui; Yin, Qi; Zhang, An-An; Zhang, Yuan [Angewandte Chemie - International Edition, 2022, vol. 61, # 6][Angew. Chem., 2022, vol. 134, # 6]

85
manganese(II) acetate [ No CAS ]
[ 14609-54-2 ]
manganase(II)-5,10,15,20-tetra(4-carboxyphenyl)porphine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide at 150℃; for 2h;	General procedure: Metalloporphyrins (MTCPPs) were prepared by refluxing TCPP with metal sources (copper(II) chloride dihydrate, zinc(II) acetate dihydrate, iron(III) chloride, manganese(II) acetate) in dimethylformamide (DMF) at 150°C for 2 h. DMF was removed, and MTCPPs were precipitated by adding water. The precipitate was dissolved in NaOH solution and reprecipitated by adding HCl solution. MTCPP were obtained after dissolved in ethanol and evaporated [6].
	In N,N-dimethyl-formamide

Reference： [1]Chanhom, Padtaraporn; Charoenlap, Nisanart; Manipuntee, Chonnavee; Insin, Numpon [Journal of Magnetism and Magnetic Materials, 2019, vol. 475, p. 602 - 610]
[2]Shen, Hai M.; Ye, Hong L.; Wang, Qin; Hu, Meng Y.; Liu, Lei; She, Yuan B. [Journal of Porphyrins and Phthalocyanines, 2021, vol. 25, # 4, p. 314 - 322]

86
uranyl nirate hexahydrate [ No CAS ]
[ 14609-54-2 ]
[(CH₃)₄N]₄[(UO₂)₄(tetrakis(4-carboxyphenyl)porphyrin)₃] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In water; N,N-dimethyl-formamide; trifluoroacetic acid at 120℃; for 12h; Autoclave; High pressure;

Reference： [1]Shao, Lang; Yue, Guozong; Li, Yingru; Chu, Mingfu; Zhai, Fuwan; Wang, Yanlong; Wang, Shuao [Dalton Transactions, 2019, vol. 48, # 5, p. 1595 - 1598]

87
zinc(II) nitrate hexahydrate [ No CAS ]
uranyl nirate hexahydrate [ No CAS ]
[ 14609-54-2 ]
[(CH₃)₄N]₄[(UO₂)₄(Zn(tetrakis(4-carboxyphenyl)porphyrin))₃] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In water; N,N-dimethyl-formamide; trifluoroacetic acid at 120℃; for 12h; Autoclave; High pressure;

Reference： [1]Shao, Lang; Yue, Guozong; Li, Yingru; Chu, Mingfu; Zhai, Fuwan; Wang, Yanlong; Wang, Shuao [Dalton Transactions, 2019, vol. 48, # 5, p. 1595 - 1598]

88
[ 14609-54-2 ]
[ 7646-85-7 ]
5,10,15,20-tetrakis(4-carboxyphenyl)porphyrinatozinc(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In N,N-dimethyl-formamide for 12h;	3.1.2. Synthesis of 1b The ligand meso-tetra(4-carboxyphenyl)porphyrin, TCPP, was synthesized by a reportedprocedure [undefined]. A sample of 0.1 g (0.126 mmol) of TCPP and 0.07 g (0.514 mmol)of zinc chloride (ZnCl2) was warmed in 100 mL DMF for 12 h in a round bottom flaskand the solution was cooled to room temperature. To the reaction mixture, 120 mL ofdeionized water was added and allowed to stand overnight. Then conc. HCl wasadded to obtain precipitate of ZnTCPP; the solid residue was then washed and driedunder vacuum [undefined]. The yield of the compound was 90%. Molecular formula:C48H28N4O8Zn; UV/Vis (in MeOH) max, λnm(ε): 425(98000), 558(5900), 596(2700),mol1dm3cm1; IR analysis gives characteristic peaks at 535, 797, 866, 990, 1100, 1287, 1431, 1597, 1686, 2540 and 3436 cm1. 1H NMR (400 MHz, CD3OD, 298 K): (δ, ppm) 8.8(s, 8H, b-pyrrolic protons); 8.4 (s, 8H, phenylic protons); 8.2 (s, 8 H, phenylic protons).The molecular ion peak was at m/z: 852.1 (852.1).
80.4%	In N,N-dimethyl-formamide at 100℃; for 7h;	5,10,15,20-Tetrakis(4-carboxyphenyl)porphyrininato-Zicn(II), (TCPP-Zn(II)) TCPP-Zn(II) was preparedby mixing TCPP (0.5859 mmol) and ZnCl2(1.4673 mmol)in DMF (80 mL); the mixture was allowed to stir for 7 h at100 °C open to the atmosphere (Manke et al. 2014). TheTCPP-Zn(II) was purified by means of column chromatographyusing alumina as stationary phase and petroleumether:ethyl acetate (5:1) as the mobile phase (rf = 0.81).Yield 0.402 g (80.4%), melting point > 300 °C; UV-Vis(ethyl acetate) λ (nm): 422, 554, 592.
	In N,N-dimethyl-formamide at 140℃; for 4h;

	In N,N-dimethyl-formamide at 175℃; for 0.0833333h; Microwave irradiation;
	In N,N-dimethyl-formamide for 6h; Reflux;

Reference： [1]Borah, Karishma Devi; Bhuyan, Jagannath [Journal of Coordination Chemistry, 2019, vol. 72, # 13, p. 2251 - 2260]
[2]Espitia-Almeida, Fabián; Díaz-Uribe, Carlos; Vallejo, William; Peña, Orlando; Gómez-Camargo, Doris; Bohórquez, Arnold R. Romero; Zarate, Ximena; Schott, Eduardo [Chemical Papers, 2021, vol. 75, # 9, p. 4817 - 4829]
[3]Ning, Xingming; Lu, Bingzhang; Zhang, Zhen; Du, Peiyao; Ren, Hongxia; Shan, Duoliang; Chen, Jing; Gao, Yunjing; Lu, Xiaoquan [Angewandte Chemie - International Edition, 2019, vol. 58, # 47, p. 16800 - 16805][Angew. Chem., 2019, vol. 131, # 47, p. 16956 - 16961,6]
[4]Carrasco, Sergio; Martín-Matute, Belén; Sanz-Marco, Amparo [Organometallics, 2019]
[5]Elsner, Martin; Fischer, Roland A.; Hou, Shujin; Li, Weijin; Mukherjee, Soumya; Zhou, Zhenyu [Angewandte Chemie - International Edition, 2021, vol. 60, # 37, p. 20551 - 20557][Angew. Chem., 2021, vol. 133, # 37, p. 20714 - 20721]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	14609-54-2	MDL No. :	MFCD00064860
Formula :	C₄₈H₃₀N₄O₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HHDUMDVQUCBCEY-UHFFFAOYSA-N
M.W :	790.77	Pubchem ID :	86278368
Synonyms :	TCPP	Chemical Name :	4,4,4,4-(Porphine-5,10,15,20-tetrayl)tetrakis(benzoic acid)

Num. heavy atoms :	60
Num. arom. heavy atoms :	34
Fraction Csp3 :	0.0
Num. rotatable bonds :	8
Num. H-bond acceptors :	10.0
Num. H-bond donors :	6.0
Molar Refractivity :	231.31
TPSA :	205.5 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.08 cm/s

Log Po/w (iLOGP) :	3.76
Log Po/w (XLOGP3) :	8.51
Log Po/w (WLOGP) :	6.03
Log Po/w (MLOGP) :	3.41
Log Po/w (SILICOS-IT) :	8.05
Consensus Log Po/w :	5.95

[ CAS No. 14609-54-2 ] {[proInfo.proName]}

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Medicinal Chemistry

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[ 14609-54-2 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

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Inquiry

Lipinski :	3.0
Ghose :	None
Veber :	1.0
Egan :	2.0
Muegge :	5.0
Bioavailability Score :	0.11

Log S (ESOL) :	-10.0
Solubility :	0.0000000799 mg/ml ; 0.0000000001 mol/l
Class :	Poorly soluble
Log S (Ali) :	-12.7
Solubility :	0.0000000002 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-12.68
Solubility :	0.0000000002 mg/ml ; 0.0 mol/l
Class :	Insoluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	7.86

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
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Prevention
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling