[ CAS No. 116206-75-8 ] {[proInfo.proName]}

Name: 116206-75-8|4,4-(10,20-Diphenyl-21H ,23H -porphine-5,15-diyl)bis[benzenamine]|98%
Brand: Ambeed
SKU: A1154799
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2D 3D

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Quality Control of [ 116206-75-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 116206-75-8 ]

SDS Specification

Alternatived Products of [ 116206-75-8 ]

Product Details of [ 116206-75-8 ]

CAS No. :	116206-75-8	MDL No. :
Formula :	C₄₄H₃₂N₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FNUGBWUULHWQCC-UHFFFAOYSA-N
M.W :	644.77	Pubchem ID :	136744721
Synonyms :

Calculated chemistry of [ 116206-75-8 ]

Physicochemical Properties

Num. heavy atoms :	50
Num. arom. heavy atoms :	34
Fraction Csp3 :	0.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	4.0
Molar Refractivity :	212.28
TPSA :	108.34 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.69
Log Po/w (XLOGP3) :	9.05
Log Po/w (WLOGP) :	6.41
Log Po/w (MLOGP) :	3.87
Log Po/w (SILICOS-IT) :	8.69
Consensus Log Po/w :	6.54

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-9.78
Solubility :	0.000000107 mg/ml ; 0.0000000002 mol/l
Class :	Poorly soluble
Log S (Ali) :	-11.22
Solubility :	0.0000000039 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-14.69
Solubility :	0.0 mg/ml ; 0.0 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	7.59

Safety of [ 116206-75-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 116206-75-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 116206-75-8 ]

[ 116206-75-8 ] Synthesis Path-Downstream 1~34

1
[ 917-23-7 ]
[ 116206-75-8 ]
5,10-bis(4-aminophenyl)-15,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; nitric acid; acetic acid; tin(ll) chloride 1.) 5 h, 2.) CHCl₃, reflux, overnight; Multistep reaction;

Reference： [1]Meng; James; Skov [Canadian Journal of Chemistry, 1994, vol. 72, # 9, p. 1894 - 1909]

2
[ 116206-75-8 ]
5,15-bis(4-aminophenyl)-10,20-bis(4-4-sulfonatophenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid for 4h; Heating;

Reference： [1]Meng; James; Skov; Korbelik [Canadian Journal of Chemistry, 1994, vol. 72, # 12, p. 2447 - 2457]

3
[ 917-23-7 ]
[ 116206-75-8 ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: 5,15,10,20-tetraphenylporphyrin With nitric acid In chloroform at 2℃; Stage #2: With hydrogenchloride; tin(ll) chloride
22.1%	Stage #1: 5,15,10,20-tetraphenylporphyrin With trifluoroacetic acid at 20℃; for 0.25h; Stage #2: With sodium nitrite for 0.1h; Further stages;	3.3; 5.3; 6.3 Weigh 5,10-bis(4-nitrophenyl)-15,20-diphenylporphyrin obtained in step (2) with 5,15-bis(4-nitrophenyl)-10,20- Diphenylporphyrin (0.7 g, 1 mmol) was added to a 100 mL Schlenk bottle, and under a argon atmosphere, 30 mL of concentrated hydrochloric acid was added to the flask and stirred for 20 min, then stannous chloride (2.2 g, 10 mmol) was added. The balloon was kept under pressure and reacted at 65 ° C for 2 h. After the reaction, the reaction solution was transferred to 100 mL of ice water to quench the reaction, and added with ammonia to a pH of about 8, with dichloromethane as an extractant, and the organic phase was extracted with a saturated sodium chloride solution, dried over anhydrous sodium sulfate. The solvent was evaporated to dryness, and the crude product was purified eluting with methylene chloride/acetone (50/1: v/v) eluting with silica gel column chromatography to give 5,15-bis(4-aminophenyl)-10,20 - Diphenylporphyrin. The yield was 22.1%.
	Stage #1: 5,15,10,20-tetraphenylporphyrin With nitric acid In dichloromethane Inert atmosphere; Stage #2: With hydrogenchloride; tin(ll) chloride In dichloromethane; water Inert atmosphere;

Multi-step reaction with 2 steps 1: sodium nitrite; trifluoroacetic acid / 0.08 h / 20 °C 2: hydrogenchloride; tin(II) chloride dihdyrate / water / 2 h / 65 °C / Inert atmosphere

Reference： [1]Hayvali; Gündüz; Gündüz; Kiliç; Hökelek [Journal of Molecular Structure, 2000, vol. 525, # 1-3, p. 215 - 226]
[2]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN108715591, 2018, A Location in patent: Paragraph 0080; 0085-0087; 0090-0092; 0122-0124; 0152-0154
[3]Tu, Siyu; Kim, Se Hye; Joseph, Jojo; Modarelli, David A.; Parquette, Jon R. [Journal of the American Chemical Society, 2011, vol. 133, # 47, p. 19125 - 19130]
[4]Xue, Yudong; Tian, Jia; Liu, Zhiyong; Chen, Jianbo; Wu, Mengsi; Shen, Yongjia; Zhang, Weian [Biomacromolecules, 2019, vol. 20, # 7, p. 2796 - 2808]

4
[ 116206-75-8 ]
[ 74-88-4 ]
C₅₀H₄₆N₆⁽²⁺⁾*2I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With diisopropylamine In N,N-dimethyl-formamide at 20℃;
	With diisopropylamine Inert atmosphere;

Reference： [1]Kessel, David; Luguya, Raymond; Vicente, M. Graca H. [Photochemistry and Photobiology, 2003, vol. 78, # 5, p. 431 - 435]
[2]Location in patent: body text Jensen, Timothy J.; Vicente, M. Graca H.; Luguya, Raymond; Norton, Jolanna; Fronczek, Frank R.; Smith, Kevin M. [Journal of Photochemistry and Photobiology B: Biology, 2010, vol. 100, # 2, p. 100 - 111]

5
[ 917-23-7 ]
[ 116206-75-8 ]
5,10-bis(4-aminophenyl)-15,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 43% 2: 21%	Stage #1: 5,15,10,20-tetraphenylporphyrin With trifluoroacetic acid; sodium nitrite at 20℃; for 0.025h; Stage #2: With hydrogenchloride; tin(ll) chloride Further stages.;
	Stage #1: 5,15,10,20-tetraphenylporphyrin With nitric acid In dichloromethane at 0℃; for 3h; Stage #2: With sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 60℃; for 4h; Overall yield = 31 %; Overall yield = 0.63 g;	2.2.2. Synthesis of di(4-aminophenyl)-diphenyl porphyrin [TPP-(NH2)2](TAPP) Synthesized from the corresponding TPP by a literature method [32] (as shown in Scheme 1). The TPP (2.0 g, 3.3 mmol) was added to CH2Cl2 (60 mL) subsequently added nitric acid fuming (5.7 g, 90 mmol), the mixture solution was stirred at 0 °C for 3 h. Then added ammonia liquor and deionized water until the filtrate was neutral (pH=7-8) to obtain purple crystals. The crude product was dried under vacuum (80 °C) for 12 h. The crude compound was purified by silica gel column chromatography with dichloromethane-petroleum ether (1:4 v/v) as eluent to afford the desired dye as purple solid (TNPP). The as-obtained TNPP was reduced into TAPP. Typically, TNPP (0.90 g, 1.3 mmol) and Na2S·9H2O (6.1 g, 25 mmol) were dissolved in 35 mL DMF and then reacted at 60 °C with magnetic stirring. TLC test results were collected, after 4 h the raw material point disappeared and generated amino porphyrin mixture. Then the flask was removed from the oil bath and the mixture was dissolved in the right amount of distilled water. The precipitate was collected and vacuum drying for 24 h, resulting in a bright purple product. The crude compound was purified by silica gel column chromatography using dichloromethane-ethylacetate (200:1 v/v) as eluent to afford a mixture product of cis- and trans-diaminotetraphenylporphyrin as purple solid. It is difficult to separate cis- and trans-diaminotetraphenyl porphyrin by column chromatography, due to the close polarity of the products. Yield: 0.63 g, 31%.1H NMR (400 MHz, CDCl3) δ=8.92 (d, J=3.6 Hz, 4H), 8.82 (d,J=3.2 Hz, 4H), 8.21 (d, J=6.7 Hz, 4H), 7.99 (d, J=7.8 Hz, 4H), 7.74(q, J=6.6 Hz, 6H), 7.05 (d, J=7.8 Hz, 4H), 4.02 (s, 4H), -2.73 (s,2H) (Fig. S2).

Reference： [1]Luguya, Raymond; Jaquinod, Laurent; Fronczek, Frank R.; Vicente, M. Graça H.; Smith, Kevin M. [Tetrahedron, 2004, vol. 60, # 12, p. 2757 - 2763]
[2]Cui, Xu; Li, Yanhui; Li, Yanwei; Qiu, Baoguo; Duan, Qian [Dyes and Pigments, 2019, vol. 164, p. 237 - 243]

6
[ 917-23-7 ]
[ 116206-75-8 ]
[ 116206-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5,15,10,20-tetraphenylporphyrin With nitric acid In chloroform at 20℃; for 4h; Stage #2: With tin(ll) chloride In hydrogenchloride at 60℃; for 1h;
1: 3.4 g 2: 1.6 g	Stage #1: 5,15,10,20-tetraphenylporphyrin With acetic acid; trifluoroacetic acid; trichloroacetic acid at 0℃; for 0.25h; Inert atmosphere; Stage #2: With sodium nitrite at 0℃; for 27h; Inert atmosphere; Further stages;	5,10-bis(4-aminophenyl)-15,20-diphenylporphyrin (2b) and 5,15-bis(4-aminophenyl)-10,20-diphenylporphyrin (2c) A mixture of TPP (5.0 g, 8.13 mmol), trichloroacetic acid (130 g, 813 mmol), trifluoroaceticacid (36 mL, 488 mmol) and acetic acid (46 mL, 813 mmol) was placed into a 1000 mL roundbottomflask. The solution was stirred for 15 min at 0 °C. Sodium nitrite (7.3 g, 106 mmol) wasadded in three equal portions at intervals of 1 h. Then the reaction mixture was stirred for 24 h at0 °C. The reaction was quenched by adding water (200 mL) and extracted with dichloromethane(3 × 150 mL). The organic layer was then concentrated under vacuum to give the crude productof nitration.The nitration crude product was dissolved in concentrated hydrochloric acid (400 mL) and wasstirred for 30 min. Tin(II) dichloride dehydrate (9.9 g, 44 mmol) was added. The mixture washeated to 80 °C for 30 min. Water (200 mL) was poured into the reaction, then cooled to roomtemperature and stand for 24 h. The resulting green precipitate was obtained by filtration. Theprecipitate was dissolved in water (300 mL). The green solution was neutralized with ammonium hydroxide until the color changed to violet. The resulting violet precipitate was obtained byfiltration and washed with water. The product was purified on silica column eluted by themixture of dichloromethane/petroleum ether (1:4) to give the compound 2b (3.4 g, 64% yield)and 2c (1.6 g, 31% yield). The polarity of compound 2b is smaller than compound 2c.
	Stage #1: 5,15,10,20-tetraphenylporphyrin With trifluoroacetic acid; sodium nitrite at 20℃; for 0.025h; Stage #2: With palladium 10% on activated carbon; cyclohexene In N,N-dimethyl-formamide at 130℃; for 0.35h; Inert atmosphere; Microwave irradiation; regioselective reaction;

Stage #1: 5,15,10,20-tetraphenylporphyrin With trifluoroacetic acid; sodium nitrite at 20℃; for 0.0333333h; Stage #2: With hydrogenchloride; tin(ll) chloride In water at 65℃; for 4h; Overall yield = 100 mg;

Reference： [1]Imaoka, Takane; Tanaka, Reiko; Yamamoto, Kimihisa [Chemistry - A European Journal, 2006, vol. 12, # 28, p. 7328 - 7336]
[2]Meng, Shuai; Xu, Zengping; Hong, Ge; Zhao, Lihui; Zhao, Zhanjuan; Guo, Jianghong; Ji, Haiying; Liu, Tianjun [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 35 - 48]
[3]Almeida, José; Fortunǎ, Maria E.; Pricop, Lucia; Lobiuc, Andrei; Leite, Andreia; Silva, André M.N.; Monteiro, Rodrigo P.; Rangel, Maria; Harabagiu, Valeria; Silva, Ana M.G. [Journal of Porphyrins and Phthalocyanines, 2019, vol. 23, # 9, p. 1001 - 1012]
[4]Sun, Chenxing; Wang, Lu; Xianyu, Banruo; Li, Tianyu; Gao, Shiqian; Xu, Huaping [Biomaterials, 2019, vol. 225]

7
[ 116206-75-8 ]
β-cyclodextrin p-phthaldehyde complex 1:1 [ No CAS ]
polymer, M_n 136858, M_w 428723 (GPC); monomer(s): β-cyclodextrin-terephthalaldehyde complex; 5,5-bis(4-aminophenyl)-10,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With acetic acid; β‐cyclodextrin In N,N-dimethyl-formamide at 20℃; for 48h;

Reference： [1]Liu, Yu; Liang, Peng; Chen, Yong; Zhang, Ying-Ming; Zheng, Jian-Yu; Yue, Hai [Macromolecules, 2005, vol. 38, # 22, p. 9095 - 9099]

8
[ 1656-44-6 ]
[ 116206-75-8 ]
5,15-bis[4-N-(2,4-dinitrobenzene)sulfonamidophenyl]-10,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With pyridine at 20℃; for 18h;

Reference： [1]Location in patent: experimental part Bhaumik, Jayeeta; Weissleder, Ralph; McCarthy, Jason R. [Journal of Organic Chemistry, 2009, vol. 74, # 16, p. 5894 - 5901]

9
5,15-bis(4′-nitrophenyl)-10,20-bisphenylporphyrin [ No CAS ]
[ 116206-75-8 ]

Yield	Reaction Conditions	Operation in experiment
32.27%	Stage #1: 5,15-bis(4′-nitrophenyl)-10,20-bisphenylporphyrin With hydrogenchloride; tin(II) chloride dihdyrate In water at 65℃; for 1.5h; Inert atmosphere; Stage #2: With ammonium hydroxide In water Inert atmosphere;
28%	With hydrogenchloride; tin(II)chloride dihydrate In water at 65℃; for 1.5h;	2.3.3. 5,10-bis(4-aminophenyl)-10,20-diphenylporphyrin (cis-DATPP) and 5,15-bis(4-aminophenyl)-10,20-diphenylporphyrin(trans-DATPP) General procedure: Both cis-DATPP and trans-DATPP were synthesized using the approach formulated by Raymond et al. [30]. Fig. 5 shows the two step reaction scheme for the syntheses of cis-DATPP and trans-DATPP. To a solution of meso-5,10,15,20-tetraphenylporphyrin(200 mg, 0.33 mmol) in trifluoroacetic acid (10 mL) was added sodium nitrite (183 mg, 2.65 mmol). After 90 s of continuous stirringat ambient room temperature, the reaction was poured intowater (100 mL) and extracted with dichloromethane (6 25 mL).The residue obtained was purified as described above and then reduced using tin(II) chloride dihydrate (0.80 g, 3.55 mmol) in concentrated hydrochloric acid (50 mL). The reaction was heated under reflux to 65 °C for 90 min, followed by cooling the solution toambient room temperature, pouring it into ice water and adjusting to pH 8 with concentrated ammonium hydroxide. The aqueousphase was extracted with dichloromethane (5 100 mL), and thecombined organic layer extracts were dried over anhydrous magnesiumsulfate. The organic phase was concentrated in vacuo andthe solutionwas pre-absorbed onto silica gel. Silica gel flash columnchromatography using a gradient mixture of dichloromethane andethyl acetate afforded first trans-DATPP, followed by cis-DATPP.Each regioisomer was recrystallized from methanol, yielding 32% ofcis-DATPP and 28% of trans-DATPP. Fig. 5 shows the reactionscheme for the preparations of cis-DATPP and trans-DATPP. cis-DATPP: 1H NMR (DMSO-d6): d (ppm) 2.83 (s, 2H, internal NH),5.48 (s, 4H, NH2), 6.93 (d, 4H, aminophenyl), 7.69-7.80 (m, 10H,phenyl), 8.08 (d, 4H, aminophenyl), 8.69 (s, 4H, b-H), 8.86 (s, 4H, b- H); ATR-IR (cm1): 3325 (NH), 1510 (NH), 800 (1,4-substitutedphenyl). trans-DATPP: 1H NMR (DMSO-d6): d (ppm) 2.81 (s, 2H,internal NH), 5.52 (s, 4H, NH2), 6.92 (d, 4H, aminophenyl),7.73-7.78 (m, 10H, phenyl), 8.22 (d, 4H, aminophenyl), 8.70 (d, 4H,b-H), 8.87 (d, 4H, b-H). ATR-IR (cm1): 3328 (NH), 1504 (NH), 800(1,4-substituted phenyl).
21.1%	With hydrogenchloride; tin(II) chloride dihdyrate In water at 65℃; for 2h; Inert atmosphere;

	With tin(II) chloride dihdyrate
	With hydrogenchloride; tin(ll) chloride In water
	With hydrogenchloride; tin(ll) chloride
200 mg	With hydrogenchloride; tin(ll) chloride Inert atmosphere; Schlenk technique;	Synthesis of 4 A solution of dipyrromethane 3 (2 g, 7.48 mmol) and benzaldehyde (0.794 g, 7.48 mmol) in chloroform (750 mL) was degassed by bubbling with nitrogen for 1 h. The reaction vessel was shielded from ambient light. Trifluoroacetic acid (1.04 mL, 7.48 mmol) was then added to one portion. The solution was stirred for 2 h at room temperature under a nitrogen atmosphere. To the reddish black reaction mixture, p-chloranil (2.76 g, 11.2 mmol) was added with overnight stirring. Triethylamine was added and then the reaction mixture was concentrated. Flash column chromatography on silicagel (CH2Cl2) yielded the desired porphyrin from the mixture as the third major band. Reprecipitation with chloroform-methanol afforded a vivid reddish purple solid. SnCl2 (1.5 g, 7.9 mmol) was added to a suspension of the above crude product (550 mg, 0.780 mmol) in concentrated HCl solution (116 mL). The reaction mixture was stirred for 45 min at room temperature and maintained at 95-100 °C for an additional 30 min. After cooling, the reaction was quenched by the slow addition of 25% ammonia. The organic layer was extracted with CHCl3 and washed with water. After standing over anhydrous Na2SO4, the organic extract was concentrated to dryness. Flash column chromatography on silicagel with CH2Cl2-ethyl acetate (30:1) as the eluent and subsequent reprecipitation from CHCl3-CH3OH gave 4 as a deep violet solid (200 mg, 0.283 mmol, 4%). 1H NMR (400 MHz, CDCl3) δ 2.75 (br s,2H), 3.99 (br s, 4H), 7.03 (d, J 8.3 Hz, 4H), 7.74 (m, 6H), 7.98 (d,J 8.3 Hz, 4H), 8.21 (d, J 9.3 Hz, 4H), 8.81 (d, J 4.8 Hz, 4H), 8.92(d, J 4.8 Hz, 4H). MS (FAB+) m/z 645 [M + H]+.

Reference： [1]Lin, Tao; Shang, Xue Song; Adisoejoso, Jinne; Liu, Pei Nian; Lin, Nian [Journal of the American Chemical Society, 2013, vol. 135, # 9, p. 3576 - 3582]
[2]Singto, Sudkanueng; Tantayanon, Supawan; Zoto, Christopher A.; Connors, Robert E. [Journal of Molecular Structure, 2018, vol. 1154, p. 114 - 130]
[3]Xue, Yudong; Tian, Jia; Liu, Zhiyong; Chen, Jianbo; Wu, Mengsi; Shen, Yongjia; Zhang, Weian [Biomacromolecules, 2019, vol. 20, # 7, p. 2796 - 2808]
[4]Location in patent: body text Bhaumik, Jayeeta; Weissleder, Ralph; McCarthy, Jason R. [Journal of Organic Chemistry, 2009, vol. 74, # 16, p. 5894 - 5901]
[5]Location in patent: experimental part Gianferrara, Teresa; Bratsos, Ioannis; Iengo, Elisabetta; Milani, Barbara; Ostric, Adrian; Spagnul, Cinzia; Zangrando, Ennio; Alessio, Enzo [Dalton Transactions, 2009, # 48, p. 10742 - 10756]
[6]Location in patent: body text Jensen, Timothy J.; Vicente, M. Graca H.; Luguya, Raymond; Norton, Jolanna; Fronczek, Frank R.; Smith, Kevin M. [Journal of Photochemistry and Photobiology B: Biology, 2010, vol. 100, # 2, p. 100 - 111]
[7]Lee, Min Hyung; Kim, Jung Won; Lee, Chang Yeon [Journal of Organometallic Chemistry, 2014, vol. 761, p. 20 - 27]

10
[ 116206-75-8 ]
5,15-bis(4-azidophenyl)-15,20-diiphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: trans-5,15-bis(4-aminophenyl)-10,20-diphenylporphyrin With trifluoroacetic acid; sodium nitrite In water at 0℃; Stage #2: With sodium azide In water at 0℃;

Reference： [1]Locos, Oliver B.; Heindl, Claudia C.; Corral, Ariadna; Senge, Mathias O.; Scanlan, Eoin M. [European Journal of Organic Chemistry, 2010, # 6, p. 1026 - 1028]

11
[ 103946-54-9 ]
[ 116206-75-8 ]
5,15-bis[4-(4-methyl-2,2'-pibyridine-4'-carboxyamidyl)phenyl]-10,20-diphenylporphyrin [ No CAS ]

Reference： [1]Dalton Transactions,2009,p. 10742 - 10756

12
[ 1346685-59-3 ]
[ 116206-75-8 ]
C₉₄H₇₆N₁₀O₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	In N,N-dimethyl-formamide at 140℃; for 18h; Inert atmosphere;

Reference： [1]Tu, Siyu; Kim, Se Hye; Joseph, Jojo; Modarelli, David A.; Parquette, Jon R. [Journal of the American Chemical Society, 2011, vol. 133, # 47, p. 19125 - 19130]

13
[ 555-16-8 ]
[ 116206-75-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: trifluoroacetic acid / 0.17 h / Inert atmosphere 2.1: propionic acid / 2.5 h / Reflux 3.1: tin(II) chloride dihdyrate; hydrogenchloride / water / 1.5 h / 65 °C / Inert atmosphere 3.2: pH 8 - 9 / Inert atmosphere

Reference： [1]Lin, Tao; Shang, Xue Song; Adisoejoso, Jinne; Liu, Pei Nian; Lin, Nian [Journal of the American Chemical Society, 2013, vol. 135, # 9, p. 3576 - 3582]

14
[ 143859-77-2 ]
[ 116206-75-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: propionic acid / 2.5 h / Reflux 2.1: tin(II) chloride dihdyrate; hydrogenchloride / water / 1.5 h / 65 °C / Inert atmosphere 2.2: pH 8 - 9 / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: chloroform / 1 h / Inert atmosphere; Schlenk technique 1.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique 1.3: Inert atmosphere; Schlenk technique 2.1: tin(ll) chloride; hydrogenchloride / Inert atmosphere; Schlenk technique

Reference： [1]Lin, Tao; Shang, Xue Song; Adisoejoso, Jinne; Liu, Pei Nian; Lin, Nian [Journal of the American Chemical Society, 2013, vol. 135, # 9, p. 3576 - 3582]
[2]Lee, Min Hyung; Kim, Jung Won; Lee, Chang Yeon [Journal of Organometallic Chemistry, 2014, vol. 761, p. 20 - 27]

15
[ 116206-75-8 ]
5,15-bis-(4-bromophenyl)-10,20-diphenyl-porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: trans-5,15-bis(4-aminophenyl)-10,20-diphenylporphyrin With sulfuric acid; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: With hydrogen bromide; copper(I) bromide In water for 2h;

Reference： [1]Lin, Tao; Shang, Xue Song; Adisoejoso, Jinne; Liu, Pei Nian; Lin, Nian [Journal of the American Chemical Society, 2013, vol. 135, # 9, p. 3576 - 3582]

16
[ 116206-75-8 ]
[ 407-25-0 ]
C₄₈H₃₀F₆N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In chloroform at 20℃; for 0.333333h; Inert atmosphere; Schlenk technique;	Synthesis of 5 A portion of 4 (200 mg, 0.283 mol), triethylamine (0.1 mL,0.849 mmol), and trifluoroacetic anhydride (178 mg, 0.849 mmol) were stirred in chloroform (20 mL) at room temperature for 20 min. TLC analysis indicated total consumption of the starting material. The reaction mixture was quenched with water and extracted with chloroform, and extracts were dried (Na2SO4). The solvent was removed by evaporation at reduced pressure and the crude product was purified by flash column chromatography on silica gel withhexane-ethyl acetate (2:1) as the eluent to give 213 mg (90%) of the desired compound. 1H NMR (400 MHz, CDCl3) d 2.74 (br s, 2H),7.76 (m, 6H), 7.97 (d, J 8.3 Hz, 4H), 8.18 (d, J 6.2 Hz, 4H), 8.24 (d,J 8.3 Hz, 4H), 8.29 (s, 2H), 8.80 (d, J 4.8 Hz, 4H), 8.85 (d,J 4.8 Hz, 4H). MS (FAB) m/z 837 [M + H]+.

Reference： [1]Lee, Min Hyung; Kim, Jung Won; Lee, Chang Yeon [Journal of Organometallic Chemistry, 2014, vol. 761, p. 20 - 27]

17
[ 100-52-7 ]
[ 116206-75-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: chloroform / 1 h / Inert atmosphere; Schlenk technique 1.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique 1.3: Inert atmosphere; Schlenk technique 2.1: tin(ll) chloride; hydrogenchloride / Inert atmosphere; Schlenk technique

Reference： [1]Lee, Min Hyung; Kim, Jung Won; Lee, Chang Yeon [Journal of Organometallic Chemistry, 2014, vol. 761, p. 20 - 27]

18
[ 917-23-7 ]
[ 67605-64-5 ]
[ 116206-75-8 ]
[ 116206-76-9 ]

Yield	Reaction Conditions	Operation in experiment
629 mg	Stage #1: 5,15,10,20-tetraphenylporphyrin With nitric acid In dichloromethane Stage #2: With sodium sulfide In N,N-dimethyl-formamide

Reference： [1]Yang, Yang; Li, Yanhui; Qiu, Nannan; Cui, Guihua; Satoh, Toshifumi; Duan, Qian [Chemistry - An Asian Journal, 2014, vol. 9, # 5, p. 1379 - 1387]

19
[ 116206-75-8 ]
C₁₉H₃₄N₂O₈ [ No CAS ]
5-(4-((S)-2,6-bis-tert-butoxycarbonylaminohexanamido)phenyl)-15-(4-aminophenyl)-10,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
128.9 mg	In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	4.2.1. General procedure for the synthesis of Boc-protected lysinemodifiedporphyrin conjugates 3a-i General procedure: BOC-Lys(BOC)-OH (1.00 equiv, 0.80 mmol) was placed into athree necked round-bottom flask. THF (15 mL)was added under theprotection of nitrogen. The mixture was cooled to -17° C. Triethylamine(1.05 equiv,117.1 μL, 0.84 mmol) and ethyl chloroformate(1.02 equiv, 77.7 μL, 0.816 mmol) were added dropwise. After theaddition was complete, the solution was stirred for 1 h while thetemperature was maintained at -17 °C. The reaction mixture wasfiltered, and the filtrate was added into the solution of aminophenyl porphyrin (0.22-1.00 equiv) in THF. Then, the reactionmixturewas stirred for 24 h at room temperature and monitored byTLC. As the reaction was completed, the reaction mixture wasevaporated in a vacuum and purified by column chromatography togive the title compound. The lysine-modified porphyrin conjugateswith different numbers of lysine molecules were synthesized bymerely tuning the ratio of the starting materials.

Reference： [1]Meng, Shuai; Xu, Zengping; Hong, Ge; Zhao, Lihui; Zhao, Zhanjuan; Guo, Jianghong; Ji, Haiying; Liu, Tianjun [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 35 - 48]

20
[ 116206-75-8 ]
C₁₉H₃₄N₂O₈ [ No CAS ]
5,15-di(4-((S)-2,6-bis-tert-butoxycarbonylaminohexanamido)phenyl)-10,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
241.9 mg	In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	4.2.1. General procedure for the synthesis of Boc-protected lysinemodifiedporphyrin conjugates 3a-i General procedure: BOC-Lys(BOC)-OH (1.00 equiv, 0.80 mmol) was placed into athree necked round-bottom flask. THF (15 mL)was added under theprotection of nitrogen. The mixture was cooled to -17° C. Triethylamine(1.05 equiv,117.1 μL, 0.84 mmol) and ethyl chloroformate(1.02 equiv, 77.7 μL, 0.816 mmol) were added dropwise. After theaddition was complete, the solution was stirred for 1 h while thetemperature was maintained at -17 °C. The reaction mixture wasfiltered, and the filtrate was added into the solution of aminophenyl porphyrin (0.22-1.00 equiv) in THF. Then, the reactionmixturewas stirred for 24 h at room temperature and monitored byTLC. As the reaction was completed, the reaction mixture wasevaporated in a vacuum and purified by column chromatography togive the title compound. The lysine-modified porphyrin conjugateswith different numbers of lysine molecules were synthesized bymerely tuning the ratio of the starting materials.

Reference： [1]Meng, Shuai; Xu, Zengping; Hong, Ge; Zhao, Lihui; Zhao, Zhanjuan; Guo, Jianghong; Ji, Haiying; Liu, Tianjun [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 35 - 48]

21
[ 116206-75-8 ]
C₁₉H₃₄N₂O₈ [ No CAS ]
5-(4-((S)-2,6-diaminohexanamido)phenyl)-15-(4-aminophenyl)-10,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

Reference： [1]Meng, Shuai; Xu, Zengping; Hong, Ge; Zhao, Lihui; Zhao, Zhanjuan; Guo, Jianghong; Ji, Haiying; Liu, Tianjun [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 35 - 48]

22
[ 100-52-7 ]
[ 143859-77-2 ]
[ 116206-75-8 ]

Yield	Reaction Conditions	Operation in experiment
6%	Stage #1: benzaldehyde; 2,2'-[(4-nitrophenyl)methylene]bis(1H-pyrrole) With chloranil; propionic acid at 120℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride; tin(ll) chloride In water at 65℃; for 15h; Inert atmosphere;

Reference： [1]Ding, Zheng-Dong; Wang, Yu-Xia; Xi, Sai-Fei; Li, Yunxing; Li, Zaijun; Ren, Xuehong; Gu, Zhi-Guo [Chemistry - A European Journal, 2016, vol. 22, # 47, p. 17029 - 17036]

23
[ 100-52-7 ]
[ 116206-75-8 ]
C₅₈H₄₀N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With trifluoroacetic acid In methanol for 10h; Inert atmosphere; Heating;

Reference： [1]Ding, Zheng-Dong; Wang, Yu-Xia; Xi, Sai-Fei; Li, Yunxing; Li, Zaijun; Ren, Xuehong; Gu, Zhi-Guo [Chemistry - A European Journal, 2016, vol. 22, # 47, p. 17029 - 17036]

24
zinc acetylacetonate dihydrate [ No CAS ]
[ 116206-75-8 ]
zinc(II) 5,15-bis(4-aminophenyl)-10,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In tetrahydrofuran for 4h; Reflux;	2.3.4. Zinc(II) 5,10-bis(4-aminophenyl)-10,20-diphenylporphyrin(cis-ZnDATPP) and zinc(II) 5,15-bis(4-aminophenyl)-10,20-diphenylporphyrin (trans-ZnDATPP) General procedure: Both cis-ZnDATPP and trans-ZnDATPP were synthesized according to Anannarukan et al. [31]. Fig. 6 shows the reaction scheme for the syntheses of cis-ZnDATPP and trans-ZnDATPP. There spective free base DATPP regioisomer was used as the starting compound for the synthesis of the zinc metalated derivative. A solution composed of cis-DATPP or trans-DATPP (638 mg,0.99 mmol) and zinc acetylacetonate dihydrate (1.28 g, 4.53 mmol)in tetrahydrofuran (190 mL) was heated under reflux for 4 h. The product mixture was concentrated in vacuo and the resulting precipitate was recrystallized from methanol to afford violet crystals.cis-ZnDATPP: Yield: 0.56 g, 80%. Melting point >300 °C. 1H NMR(DMSO-d6): d (ppm) 5.53 (s, 4H, NH2), 6.93 (d, 4H, aminophenyl), 7.68-7.85 (m, 10H, phenyl), 8.13 (d, 4H, aminophenyl), 8.69 (s, 4H,b-H), 8.86 (s, 4H, b-H). ATR-IR (cm1): 1610, 1481, 1339, 1175, 993,795. trans-ZnDATPP: Yield: 0.66 g, 85%. Melting point >300 °C. 1HNMR (DMSO-d6): d (ppm) 5.52 (s, 4H, NH2), 6.93 (d, 4H, aminophenyl),7.68-7.79 (m,10H, phenyl), 8.17 (d, 4H, aminophenyl), 8.70(d, 4H, b-H), 8.87 (d, 4H, b-H). ATR-IR (cm1): 1596, 1489, 1178, 992,795. Similar to the NMR and IR spectral data of ZnTPP, the signals atd ~ 2.8 ppm (representing the internal N-H protons) disappear, as well as the absorption band at ~3330 cm1 in the IR spectrum,indicative to porphyrin metalation.

Reference： [1]Singto, Sudkanueng; Tantayanon, Supawan; Zoto, Christopher A.; Connors, Robert E. [Journal of Molecular Structure, 2018, vol. 1154, p. 114 - 130]

25
[ 116206-75-8 ]
C₄₄H₃₆N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With pyridine; potassium carbonate; toluene-4-sulfonic acid hydrazide at 20 - 105℃; for 32h; Inert atmosphere;	3.4 Under anhydrous nitrogen, anhydrous potassium carbonate (1.1 g, 8 mmol) and 5,15-bis(4-aminophenyl)-10,20-diphenylporphyrin (0.51 g, obtained in step (3), 0.8 mmol), dissolved in 40 mL of anhydrous pyridine. Then p-toluenesulfonylhydrazide (1.5 g, 8 mmol) was added and refluxed at 105 ° C for 24 h. After the reaction was cooled, p-toluenesulfonylhydrazide (1.5 g, 8 mmol) was added under nitrogen atmosphere. After reacting for 8 h at room temperature, ethyl acetate/water (2:1, 300 mL) was added and refluxed for 1 h. The mixture was washed three times with 2 mol/L hydrochloric acid, 68% phosphoric acid solution, water, and saturated sodium hydrogen carbonate solution, and the solution was dried over anhydrous sodium sulfate and then evaporated to remove solvent. The obtained crude solid was subjected to silica gel column chromatography, using dichloromethane/hexane (2:1, v/v) as eluent. After vacuum drying, Compound 3 was obtained, which was a porphyrin sensitizer compound 3 which was absorbed by near-infrared light. The yield was 75%.

Reference： [1]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN108715591, 2018, A Location in patent: Paragraph 0080; 0093; 0094; 0095

26
[ 116206-75-8 ]
zinc 5,15-bis(4-propynylaniline)-10,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 80 °C / Inert atmosphere 2: dichloromethane; methanol / 6 h / 20 °C

Reference： [1]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN108715591, 2018, A

27
[ 116206-75-8 ]
[ 106-96-7 ]
5,15-bis(4-propynylaniline)-10,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;	5.4; 6.4 Under anhydrous nitrogen, anhydrous potassium carbonate (221 mg, 1.6 mmol) and 5,15-bis(4-aminophenyl)-10,20-diphenylporphyrin (100 mg, 0.16) obtained in the step (3). Methyl) is dissolved in 20 mL of DMF and fully dissolved. Subsequently, 2 mL of a solution of bromopropyne (190 mg, 1.6 mmol) in DMF was added, and the mixture was reacted at 80 ° C for 24 h. After cooling, the organic phase is extracted by using a saturated sodium chloride solution as dichloromethane as an extractant, and the solvent is evaporated to remove the solvent. The methylene chloride is used as an eluent to silica gel column chromatography to obtain 5,15-di(4-propynyl). Aniline)-10,20-diphenylporphyrin. The yield was 91%.

Reference： [1]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN108715591, 2018, A Location in patent: Paragraph 0125; 0126; 0127; 0155; 0156; 0157

28
[ 1656-44-6 ]
[ 116206-75-8 ]
C₅₀H₃₄N₈O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.7%	With pyridine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;

Reference： [1]Xue, Yudong; Tian, Jia; Liu, Zhiyong; Chen, Jianbo; Wu, Mengsi; Shen, Yongjia; Zhang, Weian [Biomacromolecules, 2019, vol. 20, # 7, p. 2796 - 2808]

29
[ 4480-83-5 ]
[ 116206-75-8 ]
5,15-bis[4-(N-glycolic acid amino)phenyl]-10,20-diphenylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In N,N-dimethyl-formamide at 20℃; for 18h;	2.1.2. Preparation of 5,15- bis [4-(N-glycolic acid-amino)phenyl]-10,20-diphenylporphyrin 2(opp) 5,15-bis(4-aminophenyl)-10,20-diphenylporphyrin (30.0 mg; 0.046 mmol) was dissolved in dry DMF (2 mL) and diglycolic anhydride(15.7 mg; 0.138 mmol) was added and stirred at roomtemperature for 18 h. Chloroform was added (15 mL), followed bythe addition of hexane until precipitation occurs. The solid waswashed with water and dried under vacuum affording the titlecompound (30.0 mg; 0.034 mmol; 76%). 1H NMR (300 MHz,DMSO-d6) δ ppm: 10.55 (bs, 2H, -NHOCH2-), 8.90 (d, 4H, J 4.6 Hz,H-3,7,13,17), 8.84 (d, 4H, J 4.6 Hz, H-2,8,12,18) 8.25e8.12 (m, 12H,Ho-Ar Ho,m-Arp), 7.86e7.85 (m, 6H, Hm,p-Ar), 4.36 (s, 4H,-NHOCH2-), 4.33 (s, 4H, -CH2COOH), 2.91 (s, 2H, NH). HRMS (ESITOF)for C52H40N6O8Na: calculated m/z 899.2805, found 899.2803[M+Na]+.

Reference： [1]Monteiro, Carlos J.P.; Jesus, Patricia; Davies, Matthew L.; Ferreira; Arnaut, Luis G.; Gallardo, Iluminada; Pereira, Mariette M.; Serpa, Carlos [Journal of Molecular Structure, 2019, vol. 1196, p. 444 - 454]

30
[ 623-27-8 ]
[ 64-19-7 ]
[ 116206-75-8 ]
C₉₈H₆₆N₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20.53%	With N,N-dimethyl acetamide at 150℃; for 72h; Inert atmosphere;	4 Fourth, the reaction of diaminophenylporphyrin with terephthalaldehyde to obtain a chain porphyrin polymer is as follows In a 50 mL round bottom flask,Add 48.5mg (0.07mmol) of p-diaminophenyl porphyrin trans-TPP-(NH2) 2 and 9.45 mg (0.07 mmol) of terephthalaldehyde,Soaked in 4.0 mL of N,N-dimethylacetamide (DMAc),And add 0.25ml glacial acetic acid, magnetic stirring,The reaction was refluxed at 150 ° C for 72 h under N2 protection.After the reaction is over, cool to room temperature.Filtered, the solid was washed repeatedly with tetrahydrofuran.Drying in a vacuum oven gave 11.9 mg of crude product.The yield was 20.53%

Reference： [1]Current Patent Assignee: CHANGCHUN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN110317205, 2019, A Location in patent: Paragraph 0030-0032

31
[ 917-23-7 ]
C₄₅H₃₃N₅ [ No CAS ]
[ 116206-75-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5,15,10,20-tetraphenylporphyrin With nitric acid In dichloromethane for 3h; Cooling with ice; Stage #2: With sodium sulfide In N,N-dimethyl-formamide at 60℃; for 6h; Overall yield = 49.61 percent; Overall yield = 408 mg;	3 Third, the reduction of dinitrophenyl porphyrin to diaminophenyl porphyrin by Na2S is as follows A mixture of dinitrophenylporphyrin (900 mg, 1.28 mmol) was dissolved in 35 mL of DMF.Add Na2S (6.14g, 25.53mmol),Reacted in a 60C oil bath for 6h,Then pour the reaction into 200 mL of water while hot.Place in a 0C refrigerator and let it stand overnight, then vacuum filter to obtain purple crystals.The above mixture was separated by column chromatography (dichloromethane: ethyl acetate (V/V) = 200:1) to give the p-diaminophenyl porphyrin trans-TPP-(NH2) 2 and the ortho-dinitrophenyl group. PorphyrinCi s-TPP-(NH2) 2, Yield: 408 mg, 49.61%.Tetraphenylporphyrin (2 g, 3.25 mmol) was dissolved in 60 mL of dichloromethane.Adding fuming nitric acid (5.39 g, 81.25 mmol), and reacting in an ice water bath for 3 h,TLC (Thin layer chromatography) tracking,Then add ammonia and excess nitric acid until the solution just changes from green to purple.Add water to the solution to neutrality, and remove the solvent by rotary evaporation.Drying in an oven at 60 ° C for 48 h to obtain a nitration mixture (mononitrophenylporphyrin,Ortho-dinitrophenyl porphyrin, para-dinitrophenyl porphyrin, a small amount of trinitrophenyl porphyrin), the above mixed product was subjected to column chromatography (dichloromethane: petroleum ether (V/V) = 1:4),The dinitrophenyl porphyrin ribbon was collected.Since the polarities of the two isomers of dinitrophenylporphyrin are very close,It is difficult to completely separate by column chromatography.Thus collecting 40.32%

Reference： [1]Current Patent Assignee: CHANGCHUN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN110317205, 2019, A Location in patent: Paragraph 0023-0026; 0027-0029

32
[ 7422-52-8 ]
[ 116206-75-8 ]
C₅₇H₆₄N₆O₄Si₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2%	With isopropyl alcohol In toluene at 90℃; for 72h;

Reference： [1]Almeida, José; Fortunǎ, Maria E.; Pricop, Lucia; Lobiuc, Andrei; Leite, Andreia; Silva, André M.N.; Monteiro, Rodrigo P.; Rangel, Maria; Harabagiu, Valeria; Silva, Ana M.G. [Journal of Porphyrins and Phthalocyanines, 2019, vol. 23, # 9, p. 1001 - 1012]

33
[ 116206-75-8 ]
(2R,2'R)-N,N’-((10,20-diphenylporphyrin-5,15-diyl)bis(4,1-phenylene))bis(2-aminopropanamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide / dichloromethane / 1 h / 20 °C 2: hydrogenchloride / dichloromethane / 2 h / 20 °C

Reference： [1]Liang, Xu; Najeeb-Uz-Zaman Haider, Syed; Zhu, Weihua [Dyes and Pigments, 2020, vol. 181]

34
Boc-(R)-Ala [ No CAS ]
[ 116206-75-8 ]
C₆₀H₅₈N₈O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h;	2.1. Synthesis of (R)-2-amino-N-(4-(10,15,20-triphenylporphyrin-5-yl)phenyl)-propanamide (L1) General procedure: Porphyrin having one chiral center (L1) was synthesized via N,N0 -dicyclohexylcarbodiimide (DCC) assisted coupling of chiral amino acidwith H2TAPP [22]. A 50 mL RBF was loaded with a mixture of H2TAPP(0.158 mmol, 100 mg), tert-butoxycarbonyl (BOC) protected L-Alanine(0.316 mmol, 60 mg, 2eq) and DCC (0.79 mmol, 163 mg, 5 eq). Poured25 mL freshly distilled CH2Cl2 to the above reaction mixture and stirredat rt for 30 min. Reaction progress was cautiously monitored by TLCanalysis. Dichloromethane was dried on rotavapor and removed excess followed by eluting with a mixed solvent system (eluent: CH2Cl2, 100 toMeOH:CH2Cl2, 2:98 v/v) to retrieve BOC-protected amino porphyrin(Ll-BOC). The deprotection of amine moiety of L1-BOC was carried outwith 3 N HCl in CH2Cl2. L1-BOC obtained from above reaction wastransferred to a 100 mL RBF and added 40 mL of 3 N hydrochloric acid(37%) solution. Stirred this greenish reaction mixture at rt for 2 h.Neutralized (pH 7-9) with NH3H2O and poured the reaction contentsinto a beaker containing 50 mL of CH2Cl2 and 100 mL of DI water.Separated the organic layer by solvent extraction and washed with DIwater (50 mL 3) followed by brine extraction. The collected organiclayer was dehydrated over Na2SO4, filtered and dried over rotavapor.Purified the desired compound L1 (Scheme 1) on neutral-SiO2 columnby eluting with mixed solvent system (MeOH/CH2Cl2, 1:49 v/v), followedby eluting with more polar (MeOH/CH2Cl2, 1:19 v/v) of the samemixed solvent system. Removed the solvent over rotavapor and storedproduct for further use. Chiral compound L1 was collected in 81% (90mg) Yield.

Reference： [1]Liang, Xu; Najeeb-Uz-Zaman Haider, Syed; Zhu, Weihua [Dyes and Pigments, 2020, vol. 181]

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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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 116206-75-8 ] {[proInfo.proName]}

Quality Control of [ 116206-75-8 ]

Related Doc. of [ 116206-75-8 ]

Product Details of [ 116206-75-8 ]

Calculated chemistry of [ 116206-75-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 116206-75-8 ]

[ 116206-75-8 ] Synthesis Path-Downstream 1~34

Related Parent Nucleus of [ 116206-75-8 ]

Aromatic Heterocycles

Precautionary Statements-General

Prevention

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Storage

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Physical hazards

Health hazards

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[ 116206-75-8 ]