192316-22-6

Usage

Structure

Bicyclic heterocyclic compound
The compound has a bicyclic structure consisting of a benzene ring fused to an imidazole ring.

Derivative

Benzimidazole
1H-Benzimidazole-2-methanol, alpha-methyl-,(alphaS)-(9CI) is a derivative of the parent compound benzimidazole.

Alpha-methyl group

Presence of a methyl group attached to the alpha carbon of the benzimidazole ring
The alpha-methyl group is a specific structural feature of 1H-Benzimidazole-2-methanol,alpha-methyl-,(alphaS)-(9CI).

Stereoisomer

alphaS
The compound is classified as an alphaS stereoisomer, which refers to the spatial arrangement of the alpha-methyl group in relation to the other atoms in the molecule.

Potential Applications

Pharmaceuticals, agrochemicals, or materials science
As a derivative of benzimidazole, the compound may have applications in various fields, although its specific properties and uses have not been widely documented.

Chirality

The compound exhibits chirality due to the presence of the alphaS stereoisomer designation.

Solubility

Not explicitly mentioned in the material, but as a heterocyclic compound, it may have varying solubility in different solvents (e.g., polar aprotic solvents like DMSO or protic solvents like methanol).

Upstream product

• 79-33-4 L-Lactic acid 
• 95-54-5 1,2-diamino-benzene 
• 108-05-4 vinyl acetate 
• 16414-04-3 1-benzimidazol-2-ylethanol 

Downstream Products

• 130534-57-5 (S)-4-(4-N-morpholinophenyl)-4,5-dihydro-1-methyl-1H,3H-<1,3,5>oxadiazepino<5,6-a>benzimidazole 
• 130534-52-0 (1S)-4-(3-acetylphenyl)-4,5-dihydro-1-methyl-1H,3H-<1,3,5>oxadiazepino<5,6-a>benzimidazole 
• 130534-54-2 (S)-4-(4-chlorophenyl)-4,5-dihydro-1-methyl-1H,3H-<1,3,5>oxadiazepino<5,6-a>benzimidazole 
• 130534-58-6 (S)-4-(4-sulfamidophenyl)-4,5-dihydro-1-methyl-1H,3H-<1,3,5>oxadiazepino<5,6-a>benzimidazole 
• 130534-53-1 (S)-4-(2-ethoxyphenyl)-4,5-dihydro-1-methyl-1H,3H-<1,3,5>oxadiazepino<5,6-a>benzimidazole 
• 130534-55-3 (S)-4-(4-bromophenyl)-4,5-dihydro-1-methyl-1H,3H-<1,3,5>oxadiazepino<5,6-a>benzimidazole 
• 130534-56-4 (S)-4-(4-iodophenyl)-4,5-dihydro-1-methyl-1H,3H-<1,3,5>oxadiazepino<5,6-a>benzimidazole 
• 192316-26-0 (1R,3R)-3-Ethyl-3-methyl-1-phenyl-3H-benzo[4,5]imidazo[1,2-c]oxazole 
• 2849-93-6 2-benzimidazolecarboxylic acid 
• 170031-70-6 2-(2-acetyl-1H-benzimidazol-1-yl)-1-phenylethanone 

Relevant academic research and scientific papers

Achievement of Bulky Homochirality in Zeolitic Imidazolate-Related Frameworks

Before this work, adding chiral C centers into zeolitic imidazolate frameworks (ZIFs) has never been realized. Presented here are the first examples on achieving bulky homochirality in ZIF systems, and three homochiral zeolitic imidazolate-related frameworks with sodalite and dia topologies are successfully synthesized by employing enantiopure imidazolate derivatives. The results open a new blueprint on the synthetic design of homochiral ZIFs for future applications.

Density functional theory molecular modeling, chemical synthesis, and antimicrobial behaviour of selected benzimidazole derivatives

Eco-friendly, one-pot, solvent-free synthesis of biologically active 2-substituted benzimidazoles is presented and discussed herein. Novel N-Mannich bases are synthesized from benzimidazoles, secondary amines and formaldehyde, and their structures are confirmed by 1H nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR), and elemental analysis. All benzimidazole derivatives are evaluated by qualitative and quantitative methods against 9 bacterial strains. The largest microbicide and anti-biofilm effect is observed for the 2-(1-hydroxyethyl)-compounds. Density functional theory (DFT) modeling of the molecular structure and frontier molecular orbitals, i.e. highest occupied molecular orbital and lowest unoccupied molecular orbital (HOMO/LUMO), is accomplished by using the GAMESS 2012 software. Antimicrobial activity is correlated with the electronic parameters (chemical hardness, electronic chemical potential, global electrophilicity index), Mullikan atomic charges and geometric parameters of the benzimidazole compounds. The planarity of the compound, symmetry of the molecule, and the presence of a nucleophilic group, are advantages for a high antimicrobial activity. Finally, we briefly show that further accurate processing of such compounds into thin films and hybrid structures, e.g. by laser ablation matrix-assisted pulsed laser evaporation and/or laser-induced forward transfer, may indeed provide simple and environmental friendly, state-of-the-art solutions for antimicrobial coatings.

Syntheses, Crystal Structures, and Spectral Characterization of Six Novel Benzimidazolyl Substituted Triaryltriazoles

Six new benzimidazolyl substituted triaryltriazoles, 3-(2-pyridyl)-4-(p-R-phenyl)-5-(2-benzimidazolyl)-1,2,4-triazoles (L1: R?=?OCH3; L2: R?=?CH3; L3: R?=?H; L4: R?=?Br; L5: R?=?Cl; L6: R?=?F) were successfully synthesized. Yield of L1–6 is in the range from 61 to 76%. The compounds L1–6 were characterized by UV–vis, FTIR, 1H-NMR, ESI-MS spectra, and elemental analysis. Additionally, the absolute configurations of L1–5 were determined by single crystal X-ray crystallography.

Lipase mediated kinetic resolution of benzimidazolyl ethanols

Enantioselective trans-acylation of the racemic benzimidazolyl ethanols was achieved via enzymatic kinetic resolution. A range of commercially available lipases were screened and Novozyme-435 was established as the optimal catalyst. N-Protection was found to be mandatory for effective transesterification. However, electron-withdrawing substituents reduced the enantioselectivity to some extent when compared to the other substituents.

Carbamate compositions and methods fo rmodulating the activity of the CHK1 enzyme

Described herein are carbamate compounds. Such compounds are capable of modulating the activity of a checkpoint kinase, and described herein are methods for utilizing such modulation to treat cell proliferative disorders. Also described are pharmaceutical

Asymmetric induction using chiral 1,2,4-triazole arad benzimidazole derivatives

Lithiated N-substituted 1,2,4-triazoles 3 and 8 and benzimidazole 11 reacted with (1R)-fenchone to give derivatives 5c, 9 and 12 in good yields as single diastereoisomers, (S)-Lactic acid 16 reacted with o-phenylenediamine 15 to give optically pure (S)-2-