1-Phenylbenzimidazole-2-carboxaldehyde

Base Information

• Chemical Name: 1-Phenylbenzimidazole-2-carboxaldehyde
• CAS No.: 6646-67-9
• Molecular Formula: C₁₄H₁₀N₂O
• Molecular Weight: 222.246
• DSSTox Substance ID: DTXSID301266141
• Nikkaji Number: J2.719.240H
• Mol file: 6646-67-9.mol

Synonyms:1-phenylbenzimidazole-2-carboxaldehyde;6646-67-9;SCHEMBL2086648;HJGHFDBOLBJAHJ-UHFFFAOYSA-N;DTXSID301266141;AKOS013084003;1-phenyl-1h-benzimidazole-2-carboxaldehyde

Chemical Property of 1-Phenylbenzimidazole-2-carboxaldehyde

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 222.079312947
• Heavy Atom Count: 17
• Complexity: 275

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C3=CC=CC=C3N=C2C=O

Technology Process of 1-Phenylbenzimidazole-2-carboxaldehyde

There total 5 articles about 1-Phenylbenzimidazole-2-carboxaldehyde 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: 59.0%

1-phenyl-1H-benzoimidazole (2622-60-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 1-phenyl-1H-benzo[d]imidazole-2-carbaldehyde (6646-67-9)

Guidance literature:

1-phenyl-1H-benzoimidazole; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; Inert atmosphere;

N,N-dimethyl-formamide; In diethyl ether; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1039/b820257e

Reference yield:

2-methyl-1-phenyl-1H-benzimidazole (1484-39-5) → 1-phenyl-1H-benzo[d]imidazole-2-carbaldehyde (6646-67-9)

Guidance literature:

With selenium(IV) oxide; In 1,4-dioxane; chloroform; ethyl acetate;

Reference yield:

iodobenzene (591-50-4) → 1-phenyl-1H-benzo[d]imidazole-2-carbaldehyde (6646-67-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 48 h / 120 °C / Inert atmosphere

2.1: n-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

With copper(l) iodide; n-butyllithium; caesium carbonate; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2018.08.018

upstream raw materials:

2-methyl-1-phenyl-1H-benzimidazole

1-phenyl-1H-benzoimidazole

N,N-dimethyl-formamide

benzoimidazole