7665-66-9

Usage

Benzimidazole derivative

This indicates that the compound is derived from the benzimidazole structure, which is a core structure found in many biologically active compounds.

Propyl substituent on nitrogen atom

A propyl group (a three-carbon alkyl chain) is attached to one of the nitrogen atoms in the benzimidazole ring, giving 1H-Benzimidazole,1-propyl-(9CI) its unique chemical structure.

Wide range of biological activities

Benzimidazoles are known for their diverse biological activities, which include antiviral, antifungal, and anticancer properties.

Potential pharmaceutical applications

Due to its unique chemical structure and potential biological activities, 1H-Benzimidazole, 1-propyl(9CI) may have applications in pharmaceutical research and drug development.

Need for further research

To fully understand the potential uses and properties of 1H-Benzimidazole, 1-propyl(9CI), additional studies and research are required.

InChI:InChI=1/C10H12N2/c1-2-7-12-8-11-9-5-3-4-6-10(9)12/h3-6,8H,2,7H2,1H3

Upstream product

• 796974-12-4 methyl 4-(1H-benzimidazol-1-yl)butanoate 
• 436091-31-5 4-(1-H-benzimidazol-1-yl)butanoic acid 
• 51-17-2 benzoimidazole 
• 100-46-9 benzylamine 
• 19018-22-5 1-allylbenzimidazole 
• 201230-82-2 carbon monoxide 
• 223928-08-3 1-<3-(phenylselanyl)propyl>-1H-benzimidazole 
• 108410-42-0 1-ethyl-3-propyl-benzimidazolium; iodide 

Relevant academic research and scientific papers

Catalytic Oxidative Coupling of Primary Amines under Air: A Flexible Route to Benzimidazole Derivatives

Benzimidazoles are of fundamental importance in chemistry and biology, and the development of efficient, environmentally benign methods for their preparation remains a key challenge for organic chemists. In a biomimetic approach inspired by copper amine oxidases, we disclose herein the scope and factors influencing the success of the cooperative action of CuBr2 as electron-transfer mediator and a topaquinone-like substrate-selective catalyst in the oxidative cyclocondensation of primary amines with o-aminoanilines. This one-pot atom-economic multistep process, which works under green conditions with ambient air as the terminal oxidant, low loadings of catalyst, and equimolar amounts of commercially available amine substrates, is particularly suitable for the preparation of 1,2-disubstituted benzimidazoles. Furthermore, it allows the functionalization of nonactivated primary aliphatic amines, which are known to be challenging substrates for non-enzymatic catalytic aerobic systems.

Development of a Benzimidazole-Derived Bidentate P,N-Ligand for Enantioselective Iridium-Catalyzed Hydrogenations

The development of a novel benzimidazole-derived bidentate P,N-ligand and its application in Ir-catalyzed hydrogenation is described. The ligand backbone was obtained through a one-pot tandem hydroformylation-cyclization sequence and the enantiomers of the generated alcohol were separated by chiral HPLC. By comparing the experimentally obtained CD spectra of the enantiomers with the simulated spectra generated from time-dependent DFT calculations, the absolute configuration could be obtained. The chiral alcohols could further be isolated on a larger scale after transesterification by using Candida Antarctica lipase B (Novozym 435) and could subsequently be converted into the corresponding chiral P,N-ligand by reaction with ClPPh2. The coordination properties of the racemic P,N-ligand were investigated and the molecular structure of the RhI complex [(P,N)Rh(CO)Cl] was determined by X-ray crystal structure analysis. The corresponding chiral cationic IrI complex was used as catalyst for the enantioselective hydrogenation of prochiral N-phenyl-(1-phenylethylidene)amine and trans-α-methylstilbene. For the N-aryl-substituted imine, enantiomeric excesses of only 10 % were obtained, whereas the unfunctionalized olefin could be hydrogenated with enantiomeric excesses of up to 90 %. Interestingly, the modular synthetic access to the P,N-hybrid system described here allows facile modification of the ligand structure, which should extend the scope of such novel P,N-ligands for asymmetric catalytic conversions to a large extent in the future.

Barton esters for initiator-free radical cyclisation with heteroaromatic substitution

S-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate (HOTT) facilitates the first examples of efficient radical cyclisation with (hetero)aromatic substitution via Barton ester intermediates. Cyclopropyl and alkyl radicals allow acces

Radical cyclisation onto imidazoles and benzimidazoles

New synthetic methodology has been developed for the synthesis of [1,2- a]fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(ω-alkyl) radicals are generated using Bu3SnH from N-(ω-phenylselanyl)alkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used at the leaving groups in the homolytic substitutions.