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Product Details of [ 22112-83-0 ]

CAS No. :22112-83-0
Formula : C52H38N4O8
M.W : 846.88
SMILES Code : COC(C1=CC=C(C2=C3C=CC(C(C4=CC=C(C(OC)=O)C=C4)=C5NC(C=C5)=C(C6=CC=C(C(OC)=O)C=C6)C7=NC(C=C7)=C(C8=CC=C(C(OC)=O)C=C8)C9=CC=C2N9)=N3)C=C1)=O
MDL No. :MFCD00218869
InChI Key :NVCZKUSRWBBGAH-UHFFFAOYSA-N
Pubchem ID :135414044

Safety of [ 22112-83-0 ]

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

Application In Synthesis of [ 22112-83-0 ]

* 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 [ 22112-83-0 ]

[ 22112-83-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 109-97-7 ]
  • [ 1571-08-0 ]
  • [ 22112-83-0 ]
YieldReaction ConditionsOperation in experiment
39% With acetic acid; for 4h;Reflux; Meso-tetrakis[4-(methoxycarbonyl)phenyl]porphyrinwas made through modifying A. D. Adler-f. R. Longomethod [35]. First, 2.33mmol of freshly distilled pyrroleand 2.33mmol of p-methoxycarbonylbenzaldehyde wereadded in 200ml acetic acid in a typical reaction. Then, themixture was refluxed for 4h and cooled based on the roomtemperature. The mixture was added to 100ml methanolin an ice bath after cooling. The purple crystals were filtratedand washed through using methanol and hot distilledwater. In addition, column chromatography (Silica gel, ethylacetate/n-hexane = 20:1 as an eluent) was used for purifyingcrude product, which resulted in creating a desiredpurple solid of meso-tetrakis[4-(methoxycarbonyl)phenyl]porphyrin(H2TMCPP) (39%).
37% With acetic acid; for 4h;Reflux; Meso-tetrakis[4-(methoxycarbonyl)phenyl]porphyrin wasmade through modifying of A. D. Adler-F. R. Longo method[25]. Briefly, in a typical reaction, 2.33 mmol of freshly distilledpyrrole and 2.33 mmol of p-methoxycarbonylbenzaldehydewere added into 200 mL acetic acid. The mixturewas refluxed for 4 h and cooled based on the room temperature.After cooling, the mixture was added to 100 ml methanolin an ice bath. The purple crystals were filtrated andwashed with methanol and hot distilled water. Then, crudeproduct was purified by column chromatography (silica gel,ethyl acetate /n-hexane = 20:1 as an eluent), and a desiredpurple solid of meso-tetrakis[4-(methoxycarbonyl)phenyl]porphyrin was obtained (37%).
30% With propionic acid; at 80 - 140℃; for 1h; Methyl 4-formylbenzoate (2.5g, 15.24mmol) and propionic acid (70ml) were added toa 150ml three-necked flask and heated to 80. The freshly distilled pyrrole(1ml,14.41mmol, dissolved in 10ml propionic acid) was added into the flask dropwise andthen the mixture was heated to 140. After refluxing for 1h, the solution was cooled to room tempreture and mathanol(30ml) was added into the flask and put into thefreezer for overnight. The solids were filtered out and then applied to silica gelcolumn using CH2Cl2 as eluent. Meso-tetra(4-methoxycarbonylphenyl)porphyrin(TCMPP) was obtained and the yield was 30%.MS (ESI): m/z = 847.7 [M+H]+, calcd. for C52H38N4O8 : 846.8; 1H NMR ( 400 MHz,CDCl3, TMS) δ (ppm) = 8.92 (s, 8H, pyrrole ring), 8.17-8.25(d, 16H, -C6H4), 4.08(s,12H, -CH3), -2.90 (s, 2H, pyrrloe NH); IR (KBr) υ (cm-1) : 3320, 2947, 2894, 1720,1600, 1555, 1435, 963.
23% With propionic acid; at 60℃; for 24.5h; After completely dissolving methyl-4-formylbenzoate (0.086 mol, 14.41 g) in propionic acid (250 mL) at 60C using a 500 mL 2-neck flask,Pyrrole (0.086 mol, 6.09 mL) dissolved in propionic acid (20 mL) was added dropwise over 30 minutes.Thereafter, the mixture was reacted by refluxing for 24 hours. After the reaction, the mixture was cooled to room temperature,Refrigerated for 2 hours. Then, the precipitate was recovered using suction filtration, and the recovered precipitate was ethanol,Washed with ethyl acetate and tetrahydrofuran (THF), respectively. The collected and washed precipitate was dried in an oven (70 C.) for 12 hours, As a pure product (TCPPCOOMe), a purple powder (4.9 mmol, 4.2 g, yield 23%) was obtained.
23% With propionic acid; at 140℃; for 2h;Reflux; Darkness; Pyrrole (0.69 mL, 0.01 mol), methyl p-formylbenzoate (1.64 g, 0.01 mol) and propionic acid (50 mL) were added in a three necked flask (100 mL). The resolutingsolution was refluxed for 2 h at 140 C in darkness. Then, solid powders wereobtained upon drying under vacuum. The final product was purified by columnchromatography to obtain a purple solid (0.48 g, 23%). 1H NMR (400 MHz, CDCl3 ):δ 8.83 (s, 8H), 8.46 (d, J = 10.4 Hz, 8H), 8.30 (d, J = 9.5 Hz, 8H), 4.12 (s, 12H), -2.78(s, 2H) (Fig. S1). m/z = 846.7 (Fig. S2).
21% With propionic acid; for 12h;Reflux; Darkness; pyrrole (3.0mL, 0.043mol) and methyl 4-formylbenzoate (6.9g, 0.042mol) were added to propionic acid (∼120mL) in a 500-mL flask, and the solution was refluxed for 12h in darkness. After that, the reaction mixture was cooled to room temperature and solids were collected by suction filtration and the washed with ethanol and methanol to give purple crystals (2g, 2.36mmol, 21 % yield).
20% With propionic acid; at 150℃; for 12h;Darkness; Methyl 4-formyl benzoate (2.5 g, 15.24mmol) in 25 mL of propionicacid, added pyrrole (1.02 g, 15.24 mmol) slowly in drops and it washeated (150 C) for 12 h (dark) and cooled followed by filtration to obtainedpurple solid which was purified by column chromatography.Yield (650 mg, 20%).1H NMR (CDCl3, 600 MHz), δ (ppm): -2.88 (s, 2H), 4.03 (s, 12H),8.20 (d, 8H), 8.36 (d, 8H), 8.73 (s, 8H) (Fig. S1). ESI-MS: m/z calcd.846.3, found 847.3 [M + H+] (Fig. S2).
With propionic acid;Reflux; General procedure: Porphyrin ligands were synthesized by the method of Alder with some modifications [25]. In a 100 mL of flask with three necks,0.015 mol of corresponding benzaldehyde was dissolved in 30 mL of propionic acid solution. The mixture was heated at reflux temperature with vigorous stirring. Subsequently, 0.015 mol of freshly distilled pyrrole solved in propionic acid solution (5 mL) was slowly added intothe above mixture. After a period of time of reaction, the mixture solution was cooled to room temperature and placed in the refrigerator overnight. Then the purple solid was filtered and washed with hot water and ethanol and dried at 80 C for 8 h. The crude product was purified via column chromatography using neutral alumina (100-200 mesh size) with chloroform or dichloromethane as eluent.
In acetic anhydride; propionic acid; General procedure: meso-5,10,15,20-tetraphenylporphyrins were prepared by following reported procedures24-28 via condensation reactions of the corresponding benzaldehyde with pyrrole in a mixed solvent of propionic acid and acetic anhydride. The amino functional group was obtained by reduction of nitro group using SnCl2/HCl. Carboxyl group was prepared by base-catalysed hydrolysis of ester functionality. A subsequent cobaltmetalation using Co(OAc)2•4H2O as the metal salt in DMF under reflux conditions afforded the desired cobalt complexes.
In a reaction vessel,Pyrrole (1.48 g),Methyl terephthalaldehyde (3.60 g),Chloroform (600 mL) and ethanol (9 mL) were added.There,Boron trifluoride (0.94 g) was added dropwise,The mixture was stirred for 2 hours.To this solution,2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (3.74 g) was added,And the mixture was further stirred for 1 hour.The reaction solution was passed through Celite and silica gel,The filtrate was concentrated to obtain a crude product.This was developed and separated with a silica gel column,The product (5,10,15,20-tetrakis(4-methoxycarbonylphenyl)-21H, 23H-porphyrin, 0.45 g) was obtained.
With propionic acid; at 128℃; for 1.5h; a.5,10,15,20-tetrakis(4-carboxymethyl ester)phenylporphyrinSynthesis:First, freshly steamed pyrrole and propionic acid by distillation under reduced pressure. In a 500 ml three-necked flask, 7.5 g (45 mmol) of methyl p-formylbenzoate and 200 mL of propionic acid were added.Magnetically stir and heat to 128 C, dissolve 3.1 mL (45 mmol) of pyrrole in 10 mLPropionic acid, slowly added to the propionic acid solution by drop using a constant pressure dropping funnel (about 10 min),The reaction was about 1.5 h. Stop heating, when the reaction system is cooled to below 80 C,With sufficient agitation, add 200 mL of absolute ethanol.Put it in the refrigerator and cool it overnight, and filter it to obtain a purple-black crude product.The crude product was washed several times with secondary water and absolute ethanol, respectively.Drying at 40 C under vacuum, and then separating the crude product on a silica gel column.After the first green ribbon is removed with dichloromethane as the eluent,Then use dichloromethane: ethyl acetate 2:20 as the eluent,The purple first ribbon was collected and dried to give a bright purple product.
With propionic acid; at 145℃; for 2h;Inert atmosphere; Darkness; General procedure: Tetraphenylporphyrin (TPP), tetrakis(2-chlorophenyl)porphyrin (T(2-Cl)PP), tetrakis(3-chlorophenyl)porphyrin (T(3-Cl)PP), tetrakis(4-chlorophenyl)porphyrin (T(4-Cl)PP), tetrakis(4-fluorophenyl)porphyrin (T(4-F)PP), tetrakis(4-methylphenyl)porphyrin (T(4 CH3)PP), tetrakis(4-methoxyphenyl)porphyrin (T(4 OCH3)PP), tetrakis(naphthalen-2-yl)porphyrin (T(2-Na.)P) and tetrakis(4-methoxycarbonylphenyl)porphyrin (T(4 COOCH3)PP) were synthesizedthrough condensation of the corresponding aromatic aldehydewith freshly distilled pyrrole in propionic acid according to the Adler-Longo method after some modifications (Eq. 1 in Scheme 1) [74-76].In the synthesis process, aromatic aldehyde (100 mmol) was dissolved inpropionic acid (300 mL) with stirring at the room temperature under theatmosphere of nitrogen. Then, the resultant solution was heated torefluxing (145 C), and freshly distilled pyrrole (100 mmol) was addeddropwise. After stirring and refluxing for 2.0 h under the protection oftin foil from ambient light, the resultant reaction mixture was cooled toroom temperature and kept standing at room temperature for 24.0 h.The collected precipitate from suction filtration was suspended inmethanol (200 mL) with stirring at room temperature for 6.0 h andwashed with methanol (2 × 100 mL) successively. At last, silica columnchromatography was employed for further purification using themixture of cyclohexane and dichloromethane as eluent (Vcyclohexane :Vdichloromethane = 6 : 1). All the obtained porphyrins were dried at 75 C for12.0 h under reduced pressure and characterized through FT-IR, 1HNMR, 13C NMR and ESI-MS. Details could be seen in the ElectronicSupplementary Information.
In propionic acid; at 150℃; 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%).
In propionic acid; at 130℃; for 2h;Inert atmosphere; Under N2 atmosphere, dissolve methyl p-formylbenzoate (8.2g) in propionic acid (150mL), turn on the stirring, and add the solution The temperature was raised to 130C, and newly distilled pyrrole (3.4 mL) was added dropwise. After the addition was completed, stirring was continued for 2 hours. It can be observed that the solution gradually changed from colorless to purple-black during the reaction. Then, it was cooled to room temperature, filtered to obtain a black precipitate, washed with methanol (100 mL) three times, filtered, and dried. Purified 5,10,15,20-(4-methyl formate phenyl) porphyrin was obtained by chromatography column method.
With propionic acid; for 12h;Reflux; Methyl p-formylbenzoate (6 mmol) was added to propionicacid (26 mL) in a 100-mL three-necked flask that covered with aluminumfoil. Distillated pyrrole (6 mmol) was added dropwise, andthe mixture was refluxed for 12 h. The participate was separatedby filtration and washed with methanol, ethyl acetate and THF.After drying, a purple solid was obtained as the pure product. Inthis study the concentration of the S1 in ethanol was 0.0007 M. (Scheme 2.). IR (KBr) (mmax/cm1): 3422, 3316, 2945, 1723, 1276,1105 cm1, 1H NMR (CDCl3, 300 MHz): d = 8.82 (s, 8H), 8.45 (d,J = 8.4 Hz, 8H), 8.30 (d, J = 8.4 Hz, 8H), 4.12 (s, 12H), 2.80 (s,2H) ppm.

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  • 3
  • tetrakis<4-methoxycarbonyl)phenyl>porphyrinogen [ No CAS ]
  • [ 22112-83-0 ]
  • 4
  • [ 67-56-1 ]
  • [ 14609-54-2 ]
  • [ 22112-83-0 ]
YieldReaction ConditionsOperation 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.
  • 5
  • [ 22112-83-0 ]
  • (meso-Tetra-4-methylcarboxyphenylporphyrin)palladium [ No CAS ]
  • 6
  • [ 22112-83-0 ]
  • [ 14609-54-2 ]
YieldReaction ConditionsOperation 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).

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  • 7
  • [ 109-97-7 ]
  • [ 112-54-9 ]
  • [ 167482-99-7 ]
  • [ 22112-83-0 ]
  • 5,10,15-tris[4-(methoxycarbonyl)phenyl]-20-undecyl-21H,23H-porphine [ No CAS ]
  • 5,10-bis[4-(methoxycarbonyl)phenyl]-15,20-diundecyl-21H,23H-porphine [ No CAS ]
  • 5,15-bis[4-(methoxycarbonyl)phenyl]-10,20-diundecyl-21H,23H-porphine [ No CAS ]
  • 8
  • [ 109-97-7 ]
  • [ 112-54-9 ]
  • [ 1571-08-0 ]
  • [ 22112-83-0 ]
  • 5,10,15-tris[4-(methoxycarbonyl)phenyl]-20-undecyl-21H,23H-porphine [ No CAS ]
  • 5,10-bis[4-(methoxycarbonyl)phenyl]-15,20-diundecyl-21H,23H-porphine [ No CAS ]
  • 5-[4-(methoxycarbonyl)phenyl]-10,15,20-triundecyl-21H,23H-porphine [ No CAS ]
  • 9
  • [ 22112-83-0 ]
  • [5,10,15,20-tetrakis(methyl 4-benzoate)porphyrinato]manganese(III) chloride [ No CAS ]
  • 10
  • 2,5-bis[(4-methoxycarbonylphenyl)(hydroxy)methyl]thiophene [ No CAS ]
  • [ 109-97-7 ]
  • [ 1571-08-0 ]
  • 5,10,15,20-tetra(4-methoxycarbonylphenyl)-21-thiaporphyrin [ No CAS ]
  • C52H36N2O8S2 [ No CAS ]
  • [ 22112-83-0 ]
  • 11
  • 2-[(4-methoxycarbonylphenyl)hydroxymethyl]-5-[(2-allyloxyphenyl)hydroxymethyl]thiophene [ No CAS ]
  • [ 109-97-7 ]
  • [ 1571-08-0 ]
  • 5-(2-allyloxyphenyl)-10,15,20-tri(4-methoxycarbonylphenyl)-21-thiaporphyrin [ No CAS ]
  • [ 22112-83-0 ]
  • 12
  • [ 22112-83-0 ]
  • [ 2904-62-3 ]
  • C59H41Cl2N5O9 [ No CAS ]
  • C66H44Cl4N6O10 [ No CAS ]
  • C66H44Cl4N6O10 [ No CAS ]
  • 13
  • [ 22112-83-0 ]
  • C52H36N4O8(2-)*Pt(2+) [ No CAS ]
  • 15
  • [ 22112-78-3 ]
  • [ 22112-83-0 ]
  • C100H72CeN8O12 [ No CAS ]
  • 16
  • [ 22112-83-0 ]
  • C78H60N6O15 [ No CAS ]
  • 17
  • [ 22112-83-0 ]
  • 5,10,15,20-tetrakis(4-carboxyphenyl)porphirinatozinc acetate [ No CAS ]
  • 18
  • [ 1571-08-0 ]
  • air [ No CAS ]
  • [ 22112-83-0 ]
  • 20
  • [ 22112-83-0 ]
  • [ 85857-14-3 ]
  • 21
  • [ 22112-83-0 ]
  • rhodium(III) 5,10,15,20-tetrakis(para-methoxycarbonylphenyl)porphyrin chloride [ No CAS ]
  • 22
  • [ 22112-83-0 ]
  • triruthenium dodecarbonyl [ No CAS ]
  • ruthenium(II) 5,10,15,20-tetrakis(para-methoxycarbonylphenyl)porphyrin chloride [ No CAS ]
  • 23
  • [ 22112-83-0 ]
  • 2,3,12,13-tetrabromo-5,10,15,20-tetrakis(4-methoxycarbonylphenyl)porphyrin [ No CAS ]
  • 24
  • di(rhodium)tetracarbonyl dichloride [ No CAS ]
  • [ 22112-83-0 ]
  • rhodium(III) 5,10,15,20-tetrakis(4-carboxyphenyl)porphine tetramethyl ester carbonyl chloride [ No CAS ]
  • 25
  • [ 22112-83-0 ]
  • meso-tetrakis(4-carboxyphenyl)porphyrinato aluminum(III) hydroxide [ No CAS ]
  • 26
  • [ 109-97-7 ]
  • [ 1312997-06-0 ]
  • [ 1571-08-0 ]
  • C52H37N3O9 [ No CAS ]
  • [ 22112-83-0 ]
YieldReaction ConditionsOperation in experiment
7% Methyl 4-[hydroxyl(5-{hydroxyl[3-(methoxycarbonyl)phenyl] methyl}furan-2-yl)methyl]benzoate (3, 396 mg, 1 mmol), methyl 4-formylbenzoate (328 mg, 2 mmol), and pyrrole (206 μL, 3 mmol) were dissolved in CH2Cl2 (100 mL) under nitrogen. BF3·Et2 (48%) (30 μL 0.1 mmol) was added and the reaction mixture stirred at room temperature for 1 h, followed by oxidation with DDQ (227 mg, 1 mmol) in air for an additional 1 h resulting in a mixture of two porphyrins, desired oxaporphyrin 6 and N4-porphyrin. Chromatographic separation of the crude mixture in a same way as that of oxaporphyrin 4 gives oxaporphyrin 6 as a solid product (66 mg, 7% yield). Mp>300 C; 1H NMR (300 MHz, CDCl3) δ=9.17 (s, 2H), 8.86 (s, 2H), 8.58 (d, J=4.8 Hz, 2H), 8.51 (d, J=4.8 Hz, 2H), 8.48-8.42 (m, 8H), 8.28-8.24 (m, 8H) 4.11 (s, 12H); IR (KBr, cm-1): 3438, 2924, 2852, 1723, 1607, 1434, 1278, 1112, 1018, 810; λmax (CH2Cl2) [nm (log )]: 421 (5.50), 509 (4.63), 541 (4.51), 620 (4.36), 669 (4.40); HRMS-ESI calcd for C52H37N3O9 ([M+H]+): 848.2608, found 848.2584.
  • 27
  • [ 109-97-7 ]
  • [ 171824-87-6 ]
  • [ 1571-08-0 ]
  • C50H37N3O5 [ No CAS ]
  • [ 22112-83-0 ]
YieldReaction ConditionsOperation in experiment
9% Furan-2,5-diylbis(p-tolylmethanol) (1, 308 mg, 1 mmol), methyl 4-formylbenzoate (328 mg, 2 mmol), and pyrrole (206 μL, 3.0 mmol) were dissolved in CH2Cl2 (100 mL) under nitrogen. BF3·Et2 (48%) (30 μL, 0.1 mmol) was added and the reaction mixture stirred at room temperature for 1 h, followed by oxidation with DDQ (227 mg, 1 mmol) in air for an additional 1 h resulting in a mixture of two porphyrins, desired oxaporphyrin 7 and N4-porphyrin. Chromatographic separation of the crude mixture in a same way as that of oxaporphyrion 4 gives oxaporphyrin 7 as a solid product (68 mg, 9% yield). Mp>300 C; 1H NMR (300 MHz, CDCl3) δ=9.28 (s, 2H), 8.84 (s, 2H), 8.64 (d, J=4.5 Hz, 2H), 8.60 (d, J=4.2 Hz 2H), 8.46 (d, J=8.1 Hz, 4H), 8.30 (d, J=7.8 Hz, 4H), 8.10 (d, J=7.2 Hz, 4H), 7.59 (d, J=7.8 Hz, 4H), 4.13 (s, 6H), 2.73 (s, 6H); IR (KBr, cm-1): 3438, 2924, 2852, 1723, 1607, 1434, 1275, 1109, 1021, 964, 804, 708; λmax (CH2Cl2) [nm (log )]: 421 (5.48), 508 (4.47), 541 (4.08), 592 (3.86), 674 (4.00); HRMS-ESI calcd for C50H37N3O5 ([M+H]+): 760.2811, found 760.2838.
  • 28
  • [ 1571-08-0 ]
  • C52H37N3O9 [ No CAS ]
  • [ 22112-83-0 ]
  • 29
  • [ 22112-83-0 ]
  • 5,10,15,20-tetra-p-methoxyphenylporphyrinatogold(III) chloride [ No CAS ]
  • 30
  • [ 22112-83-0 ]
  • 5,10,15,20-tetra(sodium benzoate-4-yl)porphyrinato gold(III) chloride [ No CAS ]
  • 31
  • [ 22112-83-0 ]
  • copper(II) 5,10,15,20-tetrakis(4-methoxycarbonylphenyl)porphyrinato [ No CAS ]
  • 32
  • [ 22112-83-0 ]
  • tetra methyl 4,4′,4″,4″′-(2,3,7,8,12,13,17,18-octabromoporphyrin-5,10,15,20-tetrayl)tetrabenzoate [ No CAS ]
  • 33
  • [ 109-97-7 ]
  • [ 802294-64-0 ]
  • [ 1571-08-0 ]
  • [ 22112-83-0 ]
YieldReaction ConditionsOperation in experiment
40% p-Methoxycarbonyl benzaldehyde (1.312 g, 8 mmol) was added to 100 mL of propionic acid,and then stirred at 80 C in the three-neck round flask. Pyrrole (0.56 mL, 8 mmol) was added tothe mixture through 15 min before the temperature increased to 140 C. After 1 h , thereaction mixture was cooled to room temperature under the air atmosphere. The reactionsolution was filtered, and washed with hot water and methanol to remove adsorbed acid.Purple crystal was obtained in 40 % after purification by thin-layer chromatography with silicagel-coated glass plates using methylene chloride as eluentH2(TMCPP), UV-Vis (DMF) λmax, 419 (a Soret band), 517, 550,591 and 647 (Q bands).1H NMR (500 MHz, CDCl3): δ 8.85 (s, 8H), 8.43 (d, J=10.25 Hz, 8H), 8.27 (d, J=10.25 Hz, 8H), 4.00(s, 12H), -2.83 (s, 2H); 13C NMR (126 MHz, CDCl3) δ 52.46 (CO2CH3), 119.38 (Cmeso), 127.97(ArCmeta), 129.76 (C), 134.50 (ArCortho), 146.59 (Cα), 167.21 (C=O). Elemental analysis:calculated for C52H38N4O8: C 73.82, H 4.52, N 6.62. Found: C 73.25, H 4.25, N 6.55. HighresolutionMS, calcd for C52H38N4O8: 846.2690. Found m/z: 846.2801.
  • 34
  • [ 22112-83-0 ]
  • [5,10,15,20-tetrakis(4-(methoxycarbonyl)phenyl)porphirinato]iron(III) chloride [ No CAS ]
  • 35
  • [ 22112-83-0 ]
  • [5,10,15,20-tetrakis(4-methoxycarbonylphenyl)porphyrinato]-Co(II) [ No CAS ]
 

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