Tetraphenylporphyrin

Base Information

• Chemical Name: Tetraphenylporphyrin
• CAS No.: 20998-75-8
• Deprecated CAS: 106051-94-9,15503-35-2,20998-75-8,25323-25-5,87719-36-6,15503-35-2,20998-75-8,25323-25-5,87719-36-6
• Molecular Formula: C₄₄H₃₀N₄
• Molecular Weight: 614.749
• European Community (EC) Number: 213-025-9
• NSC Number: 640184,18506
• UNII: SDB2SH8G5K
• DSSTox Substance ID: DTXSID2061272
• Nikkaji Number: J9.130H
• Wikipedia: Tetraphenylporphyrin
• Metabolomics Workbench ID: 58194
• ChEMBL ID: CHEMBL436524,CHEMBL3039846
• Mol file: 20998-75-8.mol

Synonyms:Tetraphenylporphyrin;917-23-7;5,10,15,20-tetraphenylporphyrin;meso-Tetraphenylporphine;meso-Tetraphenylporphyrin;Tetraphenylporphine;5,10,15,20-Tetraphenyl-21H,23H-porphine;21H,23H-Porphine, 5,10,15,20-tetraphenyl-;5,10,15,20-Tetraphenylporphine;meso-Tetraphenylporphyrine;CHEBI:52279;SDB2SH8G5K;20998-75-8;CHEMBL436524;MFCD00011680;NSC 18506;NSC-18506;NSC640184;NSC 640184;NSC-640184;Porphine, 5,10,15,20-tetraphenyl-;(5Z,10Z,14Z,19Z)-5,10,15,20-tetraphenyl-21,23-dihydroporphyrin;2,7,12,17-tetraphenyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaene;Tetraphenylporphryin;TPP (chelating agent);TPP;UNII-SDB2SH8G5K;meso-Tetra(phenyl)porphine;SCHEMBL30136;MESO-TETRAPHENYLPORPHIN;5,15,20-Tetraphenylporphine;meso-Tetraphenylporphyrin, 97%;CHEMBL3039846;DTXSID2061272;YNHJECZULSZAQK-LWQDQPMZSA-N;YNHJECZULSZAQK-UHFFFAOYSA-N;Porphine,10,15,20-tetraphenyl-;Tetraphenylporphyrin (Chlorin free);BCP21699;NSC18506;STR04536;BDBM50247512;meso-Tetraphenylporphine, low chlorin;STK569350;5,10,15,20-(tetraphenyl)porphyrin;AKOS002375245;21H, 5,10,15,20-tetraphenyl-;5,10,15,20-tetrakis(phenyl)porphyrin;NCI60_013368;SY009714;HY-103656;.alpha.,.gamma.,.delta.-Tetraphenylporphine;CS-0022009;T1359;Porphine, alpha,beta,gamma,delta-tetraphenyl-;5,10,15,20-Tetraphenyl-21H,23H-prophine;F14722;Porphine, 5,10,15,20-tetraphenyl- (VAN);EN300-7405378;5,10,15,20-tetraphenyl-21,23-dihydroporphyrin;.alpha.,.beta.,.gamma.,.delta.-Tetraphenylporphine;5,10,15,20-Tetraphenyl-21H,23H-porphine, 97%;5,10,15,20-TETRAPHENYL-21H,23H-PORPHYRIN;5,10,15,20-Tetraphenyl-21H,23H-porphine, >=99%;meso-Tetraphenylporphyrine pound>>5,10,15,20-tetraphenylporphyrin;meso-Tetraphenylporphyrin, suitable for fluorescence, BioReagent, >=99.0% (HPLC)

Chemical Property of Tetraphenylporphyrin

Chemical Property:

• Melting Point: 300 °C
• PSA: 56.30000
• LogP: 6.86620
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Dichloromethane (Slightly)
• XLogP3: 10.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 614.24704697
• Heavy Atom Count: 48
• Complexity: 851

Purity/Quality:

99% ^*data from raw suppliers

meso-Tetraphenylporphyrin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Porphyrins
• Canonical SMILES: C1=CC=C(C=C1)C2=C3C=CC(=C(C4=NC(=C(C5=CC=C(N5)C(=C6C=CC2=N6)C7=CC=CC=C7)C8=CC=CC=C8)C=C4)C9=CC=CC=C9)N3
• Uses: meso-Tetraphenylporphine is a photosensitizer that is often used to create coordination complexes with metals such as cobalt and rhodium. Cobalt meso-tetraphenylporphrine is used as a hydrogen catalyst. Meso-tetraphenylporphrine compounds are used as inhibitors of microtubule assembly in human cervix carcinoma cells.

Technology Process of Tetraphenylporphyrin

There total 217 articles about Tetraphenylporphyrin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

5,15-dibromo-10,20-diphenylporphyrin (1057140-05-2,151256-86-9) + phenylboronic acid (98-80-6) → 5,15,10,20-tetraphenylporphyrin (917-23-7,20998-75-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 3h;

DOI:10.1016/S0040-4039(01)01582-9

Reference yield: 85.5%

5-(2,6-N-dinitrophenyl)-10,15,20-trisphenylporphyrin → 5,15,10,20-tetraphenylporphyrin (917-23-7,20998-75-8)

Guidance literature:

5-(2,6-N-dinitrophenyl)-10,15,20-trisphenylporphyrin; With hydrogenchloride; tin(ll) chloride; In water; at 0 - 20 ℃; for 12h;

With ammonia; In water; pH=10;

Reference yield: 65.0%

benzaldehyde (100-52-7) + 5-phenyldipyrromethane (107798-98-1) → 5,15,10,20-tetraphenylporphyrin (917-23-7,20998-75-8)

Guidance literature:

benzaldehyde; 5-phenyldipyrromethane; With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 0.5h;

With selenium(IV) oxide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2011.01.044

upstream raw materials:

pyrrole

benzaldehyde

pyridine-4-carbaldehyde

p-benzyloxybenzaldehyde

Downstream raw materials:

(5Z,10Z,14Z,19Z)-5,10,15,20-Tetraphenyl-porphyrin; compound with 4-nitro-phenol

N-methyl-5,10,15,20-tetraphenylporphyrin

zinc tetraphenylporphyrin

Refernces

• 1、 Nefedov,Pavlov. "Unusual properties of tetraphenylporphyrin copper complex". . p. 449 - 451. Retrieved 2009.
• 2、 Baldwin, Jack E.,Crossley, Maxwell J.,DeBernardis, John. "EFFICIENT PERIPHERAL FUNCTIONALIZATION OF PORPHYRINS". . p. 685 - 692. Retrieved 1982.
• 3、 Rothemund. "-". . p. 2912,2913. Retrieved 1939.
• 4、 Lindsey, Jonathan S.,MacCrum, Kristy A.,Tyhonas, John S.,Chuang, Yao-Yuan. "Investigation of a Synthesis of meso-Porphyrins Employing High Concentration Conditions and an Electron Transport Chain for Aerobic Oxidation". . p. 579 - 587. Retrieved 1994.
• 5、 Senge, Mathias O,Runge, Steffen,Speck, Marcus,Ruhlandt-Senge, Karin. "Identification of stable porphomethenes and porphodimethenes from the reaction of sterically hindered aldehydes with pyrrole". . p. 8927 - 8932. Retrieved 2000.
• 6、 Paolesse, Roberto,Tagliatesta, Pietro,Boschi, Tristano. "Synthesis of unsymmetrical porphyrin dimers containing β-octaalkyl and meso-tetraphenylporphyrin subunits". . p. 2637 - 2640. Retrieved 1996.
• 7、 Rothemund,Menotti. "-". . p. 267. Retrieved 1941.
• 8、 Marrese, Carl A.,Carrano, Carl J.. "Redox Chemistry of Dichlorophosphorus(V)tetraphenylporphine: Isolation and Characterization of a Stable Porphyrin 'Anion' Radical and Possible Evidence for Internal Electron Transfer.". . p. 1279 - 1280. Retrieved 1982.
• 9、 Likhonina,Krest’yaninov,Morshnev,Kritskii,Kudayarova,Berezin. "Interaction between meso-Phenyl-Substituted Porphirinioids and Carboxylic Acids, and a Thermal Analysis of Their Cationic Salts". . p. 110 - 118. Retrieved 2020.
• 10、 Zhao, Tianxiang,Zhang, Jianbin,Yang, Xiaoxia,Xu, Qiuxia,Lan, Gongjia. "Synthesis and structural characterizations of MESO-tetraphenyl porphyrin". . p. 3050 - 3052. Retrieved 2014.