20443-38-3

Basic information

• Product Name: 5-Chloro-2-chloromethyl-1H-benzoimidazole
• Synonyms: 5-Chloro-2-chloromethyl-1H-benzoimidazole;5-Chloro-2-(chloromethyl)-1H-benzimidazole;5-Chloro-2-(chloromethyl)-1H-benzo[d]imidazole;6-CHLORO-2-(CHLOROMETHYL)-1H-BENZIMIDAZOLE;1H-BenziMidazole, 6-chloro-2-(chloroMethyl)-;5-Chloro-2-chloromethylbenzimidazole
• CAS NO: 20443-38-3
• Molecular Formula: C₈H₆Cl₂N₂
• Molecular Weight: 201.05
• EINECS: 604-604-1
• Mol File: 20443-38-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: 140 °C
• Boiling Point: 404.6 °C at 760 mmHg
• Flash Point: 230.9 °C
• Appearance: /
• Density: 1.492g/cm³
• Vapor Pressure: 2.19E-06mmHg at 25°C
• Refractive Index: 1.686
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.78±0.10(Predicted)
• CAS DataBase Reference: 5-Chloro-2-chloromethyl-1H-benzoimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-chloromethyl-1H-benzoimidazole(20443-38-3)
• EPA Substance Registry System: 5-Chloro-2-chloromethyl-1H-benzoimidazole(20443-38-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 20443-38-3(Hazardous Substances Data)

Usage

General Description

"5-Chloro-2-chloromethyl-1H-benzoimidazole" is a chemical compound that belongs to the benzoimidazole family. It is a derivative of benzoimidazole with a chlorine atom at the 5th position and a chloromethyl group at the 2nd position. 5-Chloro-2-chloromethyl-1H-benzoimidazole is used in various industrial and pharmaceutical applications, mainly as an intermediate in the synthesis of other chemicals. It has also been studied for its potential biological activities, including its antifungal and antibacterial properties. However, it is important to handle this compound with care, as it may pose hazards to human health and the environment.

InChI:InChI=1/C8H6Cl2N2/c9-4-8-11-6-2-1-5(10)3-7(6)12-8/h1-3H,4H2,(H,11,12)

Upstream product

• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 79-11-8 chloroacetic acid 
• 6953-65-7 (5-chloro-1H-benzo [d]imidazol-2-yl)methanol 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 79-04-9 chloroacetyl chloride 
• 39811-06-8 (5-chloro-1⁽³⁾H-benzimidazol-2-yl)-methanol; hydrochloride 
• 89-63-4 4-Chloro-2-nitroaniline 

Downstream Products

• 95891-99-9 N-<(2,4-dinitrophenyl)thio>-2-benzyl-6-chlorobenzimidazole 
• 91709-08-9 N-<(2,4-dinitrophenyl)thio>-2-benzyl-5-chlorobenzimidazole 
• 1535200-63-5 2-(((5-chloro-1H-benzo[d]imidazol-2-yl)methyl)thio)-6-phenylpyrimidin-4-ol 
• 1535200-45-3 2-(((5-chloro-1H-benzo[d]imidazol-2-yl)methyl)thio)-6-phenyl-N-(p-tolyl)pyrimidin-4-amine 
• 1535200-46-4 2-(((5-chloro-1H-benzo[d]imidazol-2-yl)methyl)thio)-N-(4-methoxyphenyl)-6-phenylpyrimidin-4-amine 
• 1535200-48-6 2-(((5-chloro-1H-benzo[d]imidazol-2-yl)methyl)thio)-N-(4-fluorophenyl)-6-phenylpyrimidin-4-amine 
• 1535200-50-0 2-(((5-chloro-1H-benzo[d]imidazol-2-yl)methyl)thio)-N-(4-chlorophenyl)-6-phenylpyrimidin-4-amine 
• 1535200-52-2 2-(((5-chloro-1H-benzo[d]imidazol-2-yl)methyl)thio)-6-phenyl-N-(3-(trifluoromethyl)phenyl)pyrimidin-4-amine 
• 1622873-83-9 2-(((5-chloro-1H-benzo[d]imidazol-2-yl)methyl)thio)-N-(2-methoxyphenyl)-6-phenylpyrimidin-4-amine 
• 1622873-84-0 ethyl 4-((2-(((5-chloro-1H-benzo[d]imidazol-2-yl)methyl)thio)-6-phenylpyrimidin-4-yl)amino)benzoate 
• 1535200-64-6 5-chloro-2-(((4-chloro-6-phenylpyrimidin-2-yl)thio)methyl)-1H-benzo[d]imidazole 
• 1380517-51-0 C₂₄H₁₆ClN₇OS 
• 1380517-57-6 C₂₅H₁₇BrClN₇OS 
• 1380517-53-2 C₂₅H₁₈ClN₇OS 

Relevant articles and documents

Synthesis of Benzimidazole-Fused Medium-Sized N,S-Heterocycles via Palladium-Catalyzed Cyclizations

The synthesis of unprecedented benzimidazole-fused thiazocines, thiazonines, and thiazecines having an exocyclic double bond is reported. The process proceeds through an 8-, 9-, or 10-exo-dig cyclocarbopalladation followed by reduction. The scope and limitations were established and showed the importance of the precursor structure for the success of the reaction. A competition between the exo-dig and the endo-dig cyclization was observed for two substrates bearing an N-homopropargyl chain, the endo-cyclization leading to rarely encountered 10- and 11-membered N,S-heterocycles with a trans-endocyclic double bond. X-ray structures of three products were obtained by co-crystallization with fumaric acid and show the twisted structures of these molecules.

Synthesis and antinociceptive activity of meperidine-like benzimidazole derivatives

(Graph presented) A series of novel benzimidazole derivatives have been prepared and characterized by IR, 1H-NMR spectroscopic data and elemental analysis. All the final compounds were screened for their antinociceptive activities with tail flick test. Among the synthesized compounds 3a, 4a, 4c, 8a, 9a exhibited significant antinociceptive activity. Compound 9a was found to have the highest antinociceptive activity at both 60 minutes and 120 minutes. Additionally, compounds 3a, 4a, 8a and 9a showed naloxone-reversible antinociceptive activity.

Discovery of membrane active benzimidazole quinolones-based topoisomerase inhibitors as potential DNA-binding antimicrobial agents

A series of novel benzimidazole quinolones as potential antimicrobial agents were designed and synthesized. Most of the prepared compounds exhibited good or even stronger antimicrobial activities in comparison with reference drugs. The most potent compound 15m was membrane active and did not trigger the development of resistance in bacteria. It not only inhibited the formation of biofilms but also disrupted the established Staphylococcus aureus and Escherichia coli biofilms. It was able to inhibit the relaxation activity of E. coli topoisomerase IV at 10 μM concentration. Moreover, this compound also showed low toxicity against mammalian cells. Molecular modeling and experimental investigation of compound 15m with DNA suggested that this compound could effectively bind with DNA to form a steady 15m-DNA complex which might further block DNA replication to exert the powerful bioactivities.