213133-88-1

Basic information

• Product Name: 2-(2-Chlorobenzyl)-1H-benzimidazole
• Synonyms: 2-(2-Chlorobenzyl)-1H-benzimidazole;2-[(2-chlorophenyl)methyl]-1H-benzimidazole
• CAS NO: 213133-88-1
• Molecular Formula: C₁₄H₁₁ClN₂
• Molecular Weight: 242.70354
• Mol File: 213133-88-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2-Chlorobenzyl)-1H-benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Chlorobenzyl)-1H-benzimidazole(213133-88-1)
• EPA Substance Registry System: 2-(2-Chlorobenzyl)-1H-benzimidazole(213133-88-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 213133-88-1(Hazardous Substances Data)

Usage

Chemical class

Benzimidazole

Structural feature

Benzimidazole core substituted with a chlorobenzyl group

Applications

+ Pharmaceuticals (antitumor and antifungal agent)
+ Organic synthesis (building block for complex molecules)
+ Imaging agents (diagnosing diseases such as cancer)

Properties

Unique structure and properties make it interesting for further research and development in various fields.

Upstream product

• 873-31-4 2-chlorophenylacetylene 
• 95-54-5 1,2-diamino-benzene 
• 2444-36-2 2'-chloro-benzeneacetic acid 

Relevant articles and documents

Exploration of 2-benzylbenzimidazole scaffold as novel inhibitor of NF-κB

For finding the novel inhibitor of nuclear factor κB activity, a series of benzimidazole derivatives were rationally designed, synthesized and systematically studied for their in vitro activities against LPS induced NF-κB inhibition in RAW 264.7 cells using the SEAP assay based on the flexible chalcone JSH ((E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4-hydroxy phenyl)prop-2-en-1-one) which was previously reported. Although most of the benzimidazole derivatives showed strong inhibitory activity in low micromolar potency, 2-(4-methoxybenzyl)-1H-benzo[d]imidazole (3m; IC50 = 1.7 μM) and 2-(2-methoxybenzyl)-1H-benzo[d]imidazole (3n; IC50 = 2.4 μM) showed the best inhibition. The structure activity relationship revealed that 2-benzylbenzimidazole scaffold with hydrogen bonding acceptor on phenyl ring appears as a pharmacophore.

One-pot synthesis of functionalized benzimidazoles and 1H-pyrimidines via cascade reactions of o-aminoanilines or naphthalene-1,8-diamine with alkynes and p-tolylsulfonyl azide

A one-pot synthesis of functionalized benzimidazoles and 1H-pyrimidines via the cascade reactions of o-aminoanilines or naphthalene-1,8-diamine with terminal alkynes and p-tolylsulfonyl azide is reported. The protocol is efficient and general. Georg Thiem