150613-50-6

Basic information

• Product Name: 2-(CHLOROMETHYL)-1H-BENZO[D]IMIDAZOLE-6-CARBONITRILE
• Synonyms: 2-(CHLOROMETHYL)-1H-BENZO[D]IMIDAZOLE-6-CARBONITRILE;1H-Benzimidazole-5-carbonitrile,2-(chloromethyl)-(9CI);2-(chloroMethyl)-3H-benzo[d]iMidazole-5-carbonitrile;2-Chloromethyl-3H-benzoimidazole-5-carbonitrile
• CAS NO: 150613-50-6
• Molecular Formula: C₉H₆ClN₃
• Molecular Weight: 191.62
• Product Categories: BENZIMIDAZOLE
• Mol File: 150613-50-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly, Heated, Sonicated), Methanol (Slightly)
• CAS DataBase Reference: 2-(CHLOROMETHYL)-1H-BENZO[D]IMIDAZOLE-6-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)-1H-BENZO[D]IMIDAZOLE-6-CARBONITRILE(150613-50-6)
• EPA Substance Registry System: 2-(CHLOROMETHYL)-1H-BENZO[D]IMIDAZOLE-6-CARBONITRILE(150613-50-6)

Safety Data

• Hazardous Substances Data: 150613-50-6(Hazardous Substances Data)

Usage

Description

2-(CHLOROMETHYL)-1H-BENZO[D]IMIDAZOLE-6-CARBONITRILE is an organic compound with the molecular formula C9H6ClN3. It is characterized by its benzimidazole core, which is a fused ring system consisting of a benzene and an imidazole ring. The compound also features a chloromethyl group at the 2nd position and a nitrile group at the 6th position. This structure endows it with unique chemical properties and reactivity, making it a valuable intermediate in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
2-(CHLOROMETHYL)-1H-BENZO[D]IMIDAZOLE-6-CARBONITRILE is used as a synthetic intermediate for the development of novel pharmaceutical compounds. Its unique structure allows for the creation of a wide range of derivatives with potential applications in the treatment of various diseases and medical conditions.
Used in Chemical Synthesis:
2-(CHLOROMETHYL)-1H-BENZO[D]IMIDAZOLE-6-CARBONITRILE is used as a reagent for the synthesis of benzimidazoquinoxaline derivatives under microwave irradiation. This application takes advantage of the compound's reactivity and the efficiency of microwave-assisted synthesis, leading to the production of valuable chemical intermediates for further use in the development of new materials and compounds.

Upstream product

• 237429-61-7 5-cyano-2-hydroxymethylbenzimidazole 
• 17626-40-3 4-cyano-1,2-phenylenediamine 
• 36743-66-5 ethyl chloroacetimidate hydrochloride 

Downstream Products

• 701305-29-5 ethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)-3-(5-cyano-1H-benzimidazol-2-yl)propanoate 

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.

AROMATIC AMIDINE DERIVATIVES AND SALTS THEREOF

An anticoagulant agent which comprises, as an active ingredient, an aromatic amidine derivative represented by the following general formula (1) or a salt thereof: STR1 wherein the group represented by STR2 is a group selected from indolyl, benzofuranyl, benzothienyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, naphthyl, tetrahydronaphthyl and indanyl; X is a single bond, an oxygen atom, a sulfur atom or a carbonyl group; and Y is a saturated or unsaturated 5-or 6-membered heterocyclic moiety or cyclic hydrocarbon moiety optionally having a substituent group, an amino group optionally having a substituent group or an aminoalkyl group optionally having a substituent group.The inventive compound has a high anticoagulant capacity based on its excellent FXa inhibition activity.