10394-36-2

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole,5-chloro-1-methyl-(9CI) is used as a pharmaceutical compound for its potential antimicrobial, antiviral, and anticancer properties. Benzimidazole derivatives have been shown to exhibit these biological activities, making them valuable in the development of new drugs and therapies.
Used in Organic Synthesis:
1H-Benzimidazole,5-chloro-1-methyl-(9CI) is used as a building block in the synthesis of other complex organic molecules. Its unique structure and functional groups make it a versatile component in the creation of various organic compounds for different applications.
Safety and Handling:
Proper handling and storage of 1H-Benzimidazole,5-chloro-1-methyl-(9CI) are essential to ensure safety and prevent any hazardous situations. As with any chemical compound, it is important to follow appropriate safety protocols and guidelines to minimize risks associated with its use.

InChI:InChI=1/C8H7ClN2/c1-11-5-10-7-4-6(9)2-3-8(7)11/h2-5H,1H3

Upstream product

• 17815-99-5 (4-Chloro-2-nitro-phenyl)-dimethyl-amine 
• 7647-01-0 hydrogenchloride 
• 4887-82-5 6-chloro-benzoimidazole 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 89-63-4 4-Chloro-2-nitroaniline 
• 124-38-9 carbon dioxide 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 4887-82-5 5-chloro-1H-benzimidazole 

Downstream Products

• 82040-20-8 [4-Chloro-2-(4-phenyl-imidazol-1-yl)-phenyl]-methyl-amine 
• 82040-11-7 6-Chloro-3-methyl-1-(2-oxo-2-phenyl-ethyl)-3H-benzoimidazol-1-ium; bromide 

Relevant academic research and scientific papers

Endogenous X-C=O species enable catalyst-free formylation prerequisite for CO2reductive upgrading

CO2, the main component of greenhouse gas, is currently developed as a promising surrogate of carbon feedstock. Among various conversion routes, CO2undergoing catalytic reduction can furnish hydrogen/energy carriers and value-added chemicals, while specific metal-containing catalysts or organocatalysts are often prerequisite for smooth proceeding of the involved reaction processes. In this work, both formic acid and N-containing benzoheterocyclic compounds (including various benzimidazoles, benzothiazole, and benzoxazole) along with silanols could be synthesized with high yields (>90%) from catalyst-free reductive upgrading of CO2under mild conditions (50 °C). The endogenous X-CO species, derived from the N-methyl-substituted amide-based solvent [Me2N-C(O)-R], especially PolarClean, and O-formyl group [O-C(O)-H] of in situ formed silyl formate, were found to play a prominent promotional role in the activation of the used hydrosilane for reductive CO2insertion, as demonstrated by density functional theory (DFT) calculations and isotopic labeling experiments. Moreover, reaction mechanisms and condition-based sensitivity assessment were also delineated.

Direct, Regioselective N-Alkylation of 1,3-Azoles

Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.

Supercritical methanol as solvent and carbon source in the catalytic conversion of 1,2-diaminobenzenes and 2-nitroanilines to benzimidazoles

Benzimidazoles and N-methylbenzimidazoles were synthesized by simply heating 1,2-diaminobenzenes in supercritical methanol over copper-doped porous metal oxides. These catalysts were derived from synthetic hydrotalcites that only contain earth-abundant starting materials. The carbon equivalents needed for the construction of the benzimidazole core originated from the solvent itself, which is known to undergo reforming to hydrogen and carbon monoxide through the formation of a formaldehyde intermediate. A variety of 1,2-diaminobenzenes were converted to the corresponding mixtures of benzimidazoles and N-methylated analogues in good yields. Interestingly, the more challenging, but readily available 2-nitroanilines, which require an additional reduction step prior to cyclization, could also be successfully converted to benzimidazoles in high selectivity. Furthermore, various other alcohols were applied besides methanol, to obtain 2-alkyl- and 1,2-dialkylbenzimidazoles. Preliminary mechanistic insights into the origins of N-alkylation as well as the reactivity of the nitro derivatives are discussed.

Hydroheteroarylation of alkynes under mild nickel catalysis

Nickel complexes having a bulky tri(sec-alkyl)phosphine ligand catalyze hydroheteroarylation of alkynes at 35 °C. Selective activation of an Ar-H bond over an Ar-CN bond of N-protected 3-cyanoindoles is achieved by a proper choice of ligand and/or an N-protecting group. The catalysis is applicable to a diverse range of heteroarenes to afford cis-hydroheteroarylation products in highly chemo- and stereoselective manners. Excellent regioselectivity is observed with unsymmetrical alkynes to give the corresponding heteroaryl-substituted ethenes having a larger substituent trans to an aryl group. Copyright