15-Bromo-5,10,20-triphenyl-21,22-dihydroporphyrin

Base Information

• Chemical Name: 15-Bromo-5,10,20-triphenyl-21,22-dihydroporphyrin
• CAS No.: 67066-09-5
• Molecular Formula: C38H25BrN4
• Molecular Weight: 617.54
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00469451
• Mol file: 67066-09-5.mol

Synonyms:DTXSID00469451;FT-0698789;5-Bromo-10,15,20-triphenyl-21H,23H-porphine;15-bromo-5,10,20-triphenyl-21,22-dihydroporphyrin

Chemical Property of 15-Bromo-5,10,20-triphenyl-21,22-dihydroporphyrin

Chemical Property:

• PSA: 56.30000
• LogP: 6.17030
• XLogP3: 9.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 616.12626
• Heavy Atom Count: 43
• Complexity: 834

Purity/Quality:

98%min ^*data from raw suppliers

5-Monobromo-10,15,20-triphenylporphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C3C=CC(=C(C4=CC=C(N4)C(=C5C=CC(=N5)C(=C6C=CC2=N6)Br)C7=CC=CC=C7)C8=CC=CC=C8)N3

Technology Process of 15-Bromo-5,10,20-triphenyl-21,22-dihydroporphyrin

There total 12 articles about 15-Bromo-5,10,20-triphenyl-21,22-dihydroporphyrin 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: 99.0%

10,15,20-triphenylporphyrin → 5-bromo-10,15,20-triphenylporphyrin (67066-09-5)

Guidance literature:

With N-Bromosuccinimide; In chloroform; at 0 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201200985

Reference yield: 98.0%

21H,23H-5,10,15-triphenylporphine → 5-bromo-10,20-dihexyl-15-phenylporphyrin (5) (67066-09-5)

Guidance literature:

With N-Bromosuccinimide; In chloroform; at 0 ℃;

DOI:10.1039/b516989e

Reference yield:

5,15-diphenylporphyrin (22112-89-6) → 5-bromo-10,20-dihexyl-15-phenylporphyrin (5) (67066-09-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / NBS / CH₂Cl₂ / 17 h / 0 °C

2: 97 percent / potassium phosphate hydrate; tetrakis(triphenylphosphine)palladium⁽⁰⁾ / dimethylformamide / 10 h / 90 °C

3: 95 percent / NBS / CH₂Cl₂ / 0 °C

With potassium phosphate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide; 2: Suzuki coupling;

DOI:10.1021/ja055648w

upstream raw materials:

5,15-diphenylporphyrin

phenyllithium

di(pyrrol-2-yl)methane

benzaldehyde

Downstream raw materials:

5-(3-bromophenyl)-10,15,20-triphenylporphyrin

Refernces

• 1、 Schissler, Christoph,Schneider, Erik K.,Felker, Benjamin,Weis, Patrick,Nieger, Martin,Kappes, Manfred M.,Br?se, Stefan. "A Synthetic Strategy for Cofacial Porphyrin-Based Homo- and Heterobimetallic Complexes". supporting information. p. 3047 - 3054. Retrieved 2021/01/20.
• 2、 Hayashi, Satoshi,Takamatsu, Rina,Takeda, Shiori,Noji, Masahiro,Takanami, Toshikatsu. "Central zinc metal-controlled regioselective: meso -bromination of zincated β-silylporphyrins - rapid access to meso,β-dual-functionalized porphyrins". supporting information. p. 9791 - 9795. Retrieved 2021/01/05.