4857-06-1

Basic information

• Product Name: 2-Chlorobenzimidazole
• Synonyms: 1H-Benzimidazole, 2-chloro-;2-chloro-1h-benzimidazol;Benzimidazole, 2-chloro-;TIMTEC-BB SBB006585;2-CHLORO-1H-BENZIMIDAZOLE;2-CHLORO-1H-BENZOIMIDAZOLE;2-CHLOROBENZIMIDAZOLE;AKOS B028974
• CAS NO: 4857-06-1
• Molecular Formula: C₇H₅ClN₂
• Molecular Weight: 152.58
• EINECS: 225-453-3
• Product Categories: BENZIMIDAZOLE;PHARMACEUTICAL INTERMEDIATES;Imidazol&Benzimidazole;(intermediates of norastemizole hcl);Benzimidazoles;BenzimidazolesHeterocyclic Building Blocks;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 4857-06-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: 207-211 °C(lit.)
• Boiling Point: 250.67°C (rough estimate)
• Flash Point: 182.5 °C
• Appearance: Beige to brown/Crystalline Powder
• Density: 1.2763 (rough estimate)
• Vapor Pressure: 0.000188mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.81±0.10(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Moisture Sensitive
• BRN: 116526
• CAS DataBase Reference: 2-Chlorobenzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorobenzimidazole(4857-06-1)
• EPA Substance Registry System: 2-Chlorobenzimidazole(4857-06-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4857-06-1(Hazardous Substances Data)

Usage

Chemical Properties

BEIGE TO BROWN CRYSTALLINE POWDER

Uses

2-Chlorobenzimidazole is mainly used for the synthesis of medicine and as an intermediate in organic synthesis.

Application

2-Chlorobenzimidazole can be used to synthesize the following: 1-methyl-2-chlorobenzimidazole via reaction with dimethyl sulfate1-ethyl-2-chlorobenzimidazole via reaction with diethyl sulfate1-benzyl-2-chlorobenzimidazole via reaction with benzyl chloride2-chloro-4,5,6,7-tetrabromobenzimidazole via bromination with bromineIt may be used as a building block to synthesize 4-amino-6-benzimidazole-pyrimidines.

General Description

2-Chlorobenzimidazole can be synthesized by reacting benzimidazole-2-one with phosphoryl chloride in the presence of phenol.

InChI:InChI=1/C7H5ClN2/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H,(H,9,10)

Upstream product

• 15108-18-6 2-hydrazinobenzimidazole 
• 40828-54-4 1H-benzimidazole-2-sulfonic acid 
• 1544-75-8 5-fluoro-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 64-17-5 ethanol 
• 159326-43-9 2-chloro-1-<3-(1,1-dioxythietanyl)>benzimidazole 
• 134469-07-1 Benzimidazol-2-thiol 
• 95-54-5 1,2-diamino-benzene 
• 463-73-0 carboxy chlorine 
• 615-16-7 1H-benzimidazol-2-ol 
• 39145-59-0 o-phenylenediamine hydrochloride 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 101953-62-2 2-(4-methyl-1-homopiperazino)-1H-benzimidazole 
• 133797-82-7 1-(1H-benzimidazol-2-yl)-2-methyl-pyrazolium chloride 
• 6488-88-6 2--benzimidazol 
• 84946-20-3 2-chloro-1-(4-fluorobenzyl)-1H-benzimidazole 
• 57260-68-1 2-piperazin-1-yl-1H-benzoimidazole 
• 142356-67-0 5,6-dibromo-2-chloro-1H-benzimidazole 
• 1849-02-1 2-chloro-1-methyl-benzimidazole 
• 264925-29-3 2-chloro-1-[2-[3-(4-hydroxy-2,3,5-trimethylphenoxy)-propyloxy]ethyl]-1H-benzimidazole 
• 388574-68-3 1-(4-bromo-2-fluoro-benzyl)-2-chloro-1H-benzoimidazole 

Relevant articles and documents

Design, Synthesis, Cytotoxicity, and Molecular Docking Studies of New Benzimidazole Hybrids as Possible Anticancer Agents

In the course of efforts to develop new anticancer agents, benzimidazole-based morpholine, thiomorpholine, and piperazine hybrid compounds were designed and synthesized. The structures of the synthesized compounds were confirmed by Proton nuclear magnetic resonance, Carbon-13 NMR, and mass spectroscopy. The title compounds were screened for cytotoxicity against breast and lung cancer cell lines. Compound 6c was found most active against lung cancer cell line with IC50 value of 2.11 μM and compound 10c was found most active against breast cancer cell line with IC50 of 2.23 μM. The molecular docking analysis was also carried out to explore binding pattern of compound with the target protein. All synthesized compounds showed excellent binding affinity toward target protein. Therefore, these findings will be helpful in future drug design of more potent anticancer agents.

Substituted benzimidazoles as modulators of Ras signaling

Benzimidazole compounds that increase the rate of SOS-mediated nucleotide exchange on Ras by binding to a functionally relevant, chemically tractable pocket on the SOS protein, as part of the Ras:SOS:Ras complex.

From Cells to Mice to Target: Characterization of NEU-1053 (SB-443342) and Its Analogues for Treatment of Human African Trypanosomiasis

Human African trypanosomiasis is a neglected tropical disease that is lethal if left untreated. Existing therapeutics have limited efficacy and severe associated toxicities. 2-(2-(((3-((1H-Benzo[d]imidazol-2-yl)amino)propyl)amino)methyl)-4,6-dichloro-1H-indol-1-yl)ethan-1-ol (NEU-1053) has recently been identified from a high-throughput screen of >42,000 compounds as a highly potent and fast-acting trypanocidal agent capable of curing a bloodstream infection of Trypanosoma brucei in mice. We have designed a library of analogues to probe the structure-activity relationship and improve the predicted central nervous system (CNS) exposure of NEU-1053. We report the activity of these inhibitors of T. brucei, the efficacy of NEU-1053 in a murine CNS model of infection, and identification of the target of NEU-1053 via X-ray crystallography.