5,10,15,20-tetrakis(4-methoxycarbonylphenyl)porphyrin
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; water at 75℃; for 16h; | 98% |
With potassium hydroxide In tetrahydrofuran; ethanol at 70℃; for 24h; | 96.8% |
With potassium hydroxide In tetrahydrofuran; methanol; water for 24h; Reflux; | 96% |
Conditions | Yield |
---|---|
Stage #1: pyrrole; 4-Carboxybenzaldehyde 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; | 75% |
In propionic acid for 2h; Reflux; | 55% |
With propionic acid at 20℃; for 2h; Reflux; | 55% |
Conditions | Yield |
---|---|
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 | 35% |
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; |
pyrrole
4-Carboxybenzaldehyde
propionic acid
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
for 2h; Reflux; | 26% |
Conditions | Yield |
---|---|
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 pH=< 6; |
5,10,15,20-tetrakis(4-cyanophenyl)porphirin
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; methanol |
methyl 4-formylbenzoate
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: propionic acid / 1 h / 80 - 140 °C 2: potassium hydroxide / tetrahydrofuran / 24 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: propionic acid / 1.5 h / 140 °C 2: potassium hydroxide / tetrahydrofuran; water / 48 h / 66 °C View Scheme | |
Multi-step reaction with 2 steps 1: propionic acid / 12 h / Reflux 2: sodium hydroxide / water; tetrahydrofuran; methanol / 12 h / Reflux View Scheme |
Conditions | Yield |
---|---|
In propionic acid for 0.833333h; Reflux; Inert atmosphere; |
pyrrole
propionic acid
methyl 4-formylbenzoate
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
Reflux; |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With water; potassium hydroxide In tetrahydrofuran; methanol at 120℃; for 12h; |
Conditions | Yield |
---|---|
With propionic acid for 1.5h; Reflux; |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With oxalyl dichloride In dichloromethane for 1h; | 100% |
With thionyl chloride for 10h; Substitution; Heating; | 87% |
With thionyl chloride for 2h; Heating; |
O-tert-butyl-L-serine methyl ester hydrochloride
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 18h; Inert atmosphere; | 100% |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With palladium dichloride In N,N-dimethyl-formamide at 155℃; for 0.25h; | 98% |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With thionyl chloride for 1h; Reflux; | 98% |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With sodium hydroxide | 98% |
tetrakis(4-carboxyphenyl)porphyrin
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
Conditions | Yield |
---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 18h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; dimethyl sulfoxide at 20℃; for 50h; Cooling with ice; | 96% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 48h; Reflux; |
water
tetrakis(4-carboxyphenyl)porphyrin
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
at 120℃; for 48h; | 96% |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
In methanol at 20℃; | 94% |
Conditions | Yield |
---|---|
Stage #1: tetrakis(4-carboxyphenyl)porphyrin With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide for 0.5h; Stage #2: histamine With dmap In water; N,N-dimethyl-formamide for 0.333333h; Sonication; | 90% |
zinc(II) acetate dihydrate
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
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 | 90% |
tetrakis(4-carboxyphenyl)porphyrin
zinc(II) chloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 12h; | 90% |
In N,N-dimethyl-formamide at 140℃; for 4h; | |
In N,N-dimethyl-formamide at 175℃; for 0.0833333h; Microwave irradiation; |
1-n-butyl-3-methylimidazolim bromide
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With water; nitric acid; calcium chloride In N,N-dimethyl-formamide at 110℃; for 72h; Autoclave; | 90% |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
Stage #1: cobalt(II) chloride hexahydrate; tetrakis(4-carboxyphenyl)porphyrin In dimethyl sulfoxide for 24h; Reflux; Stage #2: With hydrogenchloride In water | 89% |
In dimethyl sulfoxide for 24h; Reflux; | 80% |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
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; | 88% |
water
tetrakis(4-carboxyphenyl)porphyrin
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
at 120℃; for 48h; | 87% |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
In methanol; acetone for 24h; Inert atmosphere; Reflux; | 86% |
In N,N-dimethyl-formamide for 12h; Reflux; | |
In N,N-dimethyl-formamide at 175℃; for 0.0833333h; Microwave irradiation; |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 5h; Reflux; | 86% |
zinc diacetate
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 5h; Reflux; | 86% |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With pyridine; dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; | 85% |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
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; | 85% |
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 18h; Condensation; | 84% |
cobalt(II) diacetate tetrahydrate
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 2h; Reflux; | 84% |
In N,N-dimethyl-formamide for 1h; Reflux; | 80.7% |
In methanol; dichloromethane Reflux; | |
In N,N-dimethyl-formamide for 2h; Reflux; | |
In N,N-dimethyl-formamide for 12h; Reflux; | 222 mg |
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
Stage #1: zirconium oxide chloride octahydrate; tetrakis(4-carboxyphenyl)porphyrin In N,N-dimethyl-formamide at 130℃; for 15h; Stage #2: In N,N-dimethyl-formamide for 2h; Reflux; | 83% |
tetrakis(4-carboxyphenyl)porphyrin
tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate
Conditions | Yield |
---|---|
Stage #1: tetrakis(4-carboxyphenyl)porphyrin With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate In N,N-dimethyl-formamide at 20℃; for 24h; Cooling with ice; | 83% |
formic acid
water
tetrakis(4-carboxyphenyl)porphyrin
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
at 120℃; for 48h; | 82% |
1,3-di(4-pyridyl)propane
tetrakis(4-carboxyphenyl)porphyrin
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide at 120℃; for 8h; Autoclave; High pressure; | 82% |
Conditions | Yield |
---|---|
In acetone for 24h; Inert atmosphere; Reflux; Schlenk technique; | 82% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 20h; | 81% |
The meso-Tetra(4-carboxyphenyl)porphine with CAS registry number of 14609-54-2 is also known as Benzoicacid, 4,4',4'',4'''-(5,10,15,20-porphinetetrayl)tetra- (8CI). The IUPAC name is 4-[10,15,20-Tris(4-carboxyphenyl)-21,24-dihydroporphyrin-5-yl]benzoic acid. It belongs to product categories of Porphyrins; Synthetic Porphyrins; Analytical Chemistry; Biochemistry; Chelating Reagents; Ligands for Pharmaceutical Research; Magnetic Resonance Imaging (Chelating Reagents); Porphines. In addition, the formula is C48H30N4O8 and the molecular weight is 790.77. When you are using this chemical, do not breathe dust and avoid contact with skin and eyes.
Physical properties about meso-Tetra(4-carboxyphenyl)porphine are: (1)ACD/LogP: 7.54; (2)# of Rule of 5 Violations: 4; (3)#H bond acceptors: 12; (4)#H bond donors: 6; (5)#Freely Rotating Bonds: 8; (6)Polar Surface Area: 206.56Å2; (7)Index of Refraction: 1.734; (8) Molar Refractivity: 216.672 cm3; (9)Molar Volume: 540.517 cm3; (10)Surface Tension: 79.865 dyne/cm; (11)Density: 1.463 g/cm3.
Uses of meso-Tetra(4-carboxyphenyl)porphine: it is used to produce 4,4',4'',4'''-(21H,23H-porphine-5,10,15,20-tetrayl) tetrakis(benzoic acid chloride). The reaction occurs with reagent thionyl chloride and other condition of heating for 10 hours. The yield is about 87%.
You can still convert the following datas into molecular structure:
1.SMILES: OC(=O)c1ccc(cc1)c7c2\C=C/c(n2)c(c3nc(cc3)c(c\4nc(/C=C/4)c(c5ccc(cc5)C(O)=O)c6ccc7n6)c8ccc(cc8)C(O)=O)c9ccc(cc9)C(O)=O
2.InChI: InChI=1/C48H30N4O8/c53-45(54)29-9-1-25(2-10-29)41-33-17-19-35(49-33)42(26-3-11-30(12-4-26)46(55)56)37-21-23-39(51-37)44(28-7-15-32(16-8-28)48(59)60)40-24-22-38(52-40)43(36-20-18-34(41)50-36)27-5-13-31(14-6-27)47(57)58/h1-24,49,52H,(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40-
3.InChIKey: HHDUMDVQUCBCEY-LWQDQPMZBG
4.Std. InChI: InChI=1S/C48H30N4O8/c53-45(54)29-9-1-25(2-10-29)41-33-17-19-35(49-33)42(26-3-11-30(12-4-26)46(55)56)37-21-23-39(51-37)44(28-7-15-32(16-8-28)48(59)60)40-24-22-38(52-40)43(36-20-18-34(41)50-36)27-5-13-31(14-6-27)47(57)58/h1-24,49,52H,(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40-.
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