14625-40-2

Basic information

• Product Name: 2-(CHLOROMETHYL)-6-METHOXY-1H-BENZO[D]IMIDAZOLE
• Synonyms: 2-(CHLOROMETHYL)-6-METHOXY-1H-BENZO[D]IMIDAZOLE;1H-Benzimidazole,2-(chloromethyl)-5-methoxy-(9CI)
• CAS NO: 14625-40-2
• Molecular Formula: C₉H₉ClN₂O
• Molecular Weight: 196.63
• Product Categories: BENZIMIDAZOLE
• Mol File: 14625-40-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 405.4±25.0 °C(Predicted)
• Appearance: /
• Density: 1.339±0.06 g/cm3(Predicted)
• PKA: 11.92±0.10(Predicted)
• CAS DataBase Reference: 2-(CHLOROMETHYL)-6-METHOXY-1H-BENZO[D]IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)-6-METHOXY-1H-BENZO[D]IMIDAZOLE(14625-40-2)
• EPA Substance Registry System: 2-(CHLOROMETHYL)-6-METHOXY-1H-BENZO[D]IMIDAZOLE(14625-40-2)

Safety Data

• Hazardous Substances Data: 14625-40-2(Hazardous Substances Data)

Usage

General Description

2-(Chloromethyl)-6-methoxy-1H-benzo[d]imidazole is a chemical compound with the molecular formula C9H9ClN2O. It is a benzimidazole derivative with a chloromethyl group and a methoxy group attached to the benzene ring. 2-(CHLOROMETHYL)-6-METHOXY-1H-BENZO[D]IMIDAZOLE has potential applications in pharmaceutical and agrochemical industries due to its unique chemical structure and properties. It can be used as a building block in the synthesis of various biologically active molecules and as a precursor in the production of fungicides and pesticides. Additionally, its benzimidazole core has been found to exhibit important pharmacological activities, making it a subject of interest in drug discovery and development. Overall, 2-(Chloromethyl)-6-methoxy-1H-benzo[d]imidazole is a versatile chemical with potential applications in multiple fields and industries.

Upstream product

• 102-51-2 4-methoxy-1,2-phenylenediamine 
• 20033-99-2 (5-methoxy-1H-benzimidazole-2-yl)-methanol 
• 79-11-8 chloroacetic acid 

Downstream Products

• 1310689-28-1 2-[4-(4-⁽¹⁸⁾F-fluorobenzyl)piperidin-1-ylmethyl]benzimidazol-5-ol 
• 1310689-27-0 2-[4-(4-⁽¹⁸⁾F-fluorobenzyl)piperidin-1-yl]methyl-5-methoxybenzimidazole 
• 1310689-26-9 [1-(5-methoxybenzimidazol)-2-ylmethylpiperidin-4-yl]-(4-⁽¹⁸⁾F-fluorophenyl)methanone 
• 685841-35-4 2-(4-benzylpiperidin-1-ylmethyl)benzimidazol-5-ol 
• 685841-45-6 2-[4-(4-fluorobenzyl)piperidin-1-ylmethyl]benzimidazol-5-ol 
• 1310689-21-4 [1-(5-methoxybenzimidazol-2-ylmethyl)piperidin-4-yl]-(4-nitrophenyl)methanone 
• 1310689-33-8 2-[4-(4-fluorobenzyl)piperidin-1-yl]methyl-5-methoxybenzimidazole 
• 1310689-22-5 [1-(5-methoxybenzimidazol)-2-ylmethylpiperidin-4-yl]-(4-fluorophenyl)methanone 
• 685841-33-2 C₂₁H₂₅N₃O 
• 1310689-18-9 2-fluoro-5-[1-(5-methoxybenzimidazol-2-ylmethyl)piperidin-4-ylmethyl]-benzaldehyde 
• 1310689-19-0 2-(4-(3-[1,3-dithian-2-yl]-4-nitrobenzyl)piperidin-1-ylmethyl)-5-methoxybenzimidazole 

Relevant articles and documents

Synthesis and evaluation of selected benzimidazole derivatives as potential antimicrobial agents

A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds have some common features; three possess 5-halo substituents; two are derivatives of (S)-2-ethanaminebenzimidazole; and the others are derivatives of one 2-(chloromethyl)-1Hbenzo[ d]imidazole and (1H-benzo[d]imidazol-2-yl)methanethiol. The results from the antifungal screening were also very interesting: 23 compounds exhibited potent fungicidal activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives could be considered promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications.

Discovery of 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (ABT-724), a dopaminergic agent with a novel mode of action for the potential treatment of erectile dysfunction

A new class of agents with potential utility for the treatment of erectile dysfunction has been discovered, guided by the hypothesis that selective D 4 agonists are erectogenic but devoid of the side effects typically associated with dopaminergic agents. The lead agent 2-(4-pyridin-2-ylpiperazin- 1-ylmethyl)-1H-benzimidazole (1, ABT-724) was discovered by optimization of a series of benzimidazole arylpiperazines. This highly selective D4 agonist was found to be very potent and efficacious in vivo, eliciting penile erections in rats at a dose of 0.03 μmol/kg, with a positive response rate of 77% erectile incidence. Even at high doses, it was devoid of side effects in animal models of central nervous system behaviors, emesis, or nausea. The structure-activity relationship of the parent benzimidazole series leading to 1 is described, with the detailed in vitro and in vivo profiles described. Distinctive structural features were discovered that are associated with D 4 selective agonism in this series of analogues.