2562-94-9

Usage

Molecular structure

1H-Benzimidazole, 1-methyl-2-(2-phenylethenyl)is a heterocyclic aromatic compound with a distinctive structure, featuring a benzimidazole ring with a methyl group and a phenylethenyl group attached to it.

Derivative of benzimidazole

The compound is a derivative of benzimidazole, which is a heterocyclic aromatic compound known for its stability and diverse applications.

Unique properties

The presence of a methyl group and a phenylethenyl group on the benzimidazole ring gives 1H-Benzimidazole, 1-methyl-2-(2-phenylethenyl)- unique properties, such as enhanced solubility, stability, and reactivity.

Building block in synthesis

1H-Benzimidazole, 1-methyl-2-(2-phenylethenyl)may be used as a building block in the synthesis of pharmaceutical drugs, agrochemicals, and materials science, due to its versatile chemical structure and properties.

Upstream product

• 1632-83-3 1-Methylbenzimidazole 
• 101349-79-5 2-phenylvinyl iodide 
• 621-82-9 Cinnamic acid 
• 77-78-1 dimethyl sulfate 
• 1456-19-5 2-styryl-1H-benzo[d]imidazole 
• 95-54-5 1,2-diamino-benzene 
• 2876-08-6 1,2-dimethyl-1H-benzimidazole 
• 100-52-7 benzaldehyde 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 110818-55-8 cinnamimidoyl ethyl ether hydrochloride 
• 4760-34-3 N-methyl-1,2-phenylenediamine 

Relevant academic research and scientific papers

Unprecedented salt-promoted direct arylation of acidic sp2 C[sbnd]H bonds under heterogeneous Ni-MOF-74 catalysis: Synthesis of bioactive azole derivatives

Herein, nickel-based metal-organic framework, Ni-MOF-74, was synthesized by a solvothermal method and its properties was characterized by a host of techniques. Ni-MOF-74 exhibited exceptional catalytic activity toward the direct arylation of azoles via C[sbnd]H activation while other Ni-MOFs, nickel-based heterogeneous systems, and homogeneous counter parts displayed lower activity. Optimal conditions involved the use of Li2CO3 or KCl salts in diglyme solvent in 18 h and no additional ligand is required. This is the first and unprecedented report using KCl salt as promoter for arylation of heterocycles. By avoiding the use of strong bases and oxidants, optimized conditions are compatible with wide range of functional groups and heterocycles. Furthermore, by taking advantage of large aperture size of Ni-MOF-74, we are able to utilize optimized conditions to successfully synthesize several bioactive arylated azole derivatives. Previous studies using heterogeneous catalysts to approach these bioactive compounds are not performed in the literature. Leaching tests indicated that homogeneous catalysis via leached active nickel species is unlikely. Thus, the catalyst was facilely separated from the reaction mixture and reused several times without significant degradation of the catalytic reactivity.

Green syntheses of n-alkyl-2-styrylbenzimidazoles

Simple and green methodologies for the syntheses of 2-styrylbenzimidazoles (3a-c) and its N-alkyl derivatives (7a-i) have been developed. o-Phenylenediamine (1) was condensed with cinnamic acids (2a-c) resulting in 2-styrylbenzimidazoles (3a-c) using glycerol as a green and efficient solvent. 3 were also prepared alternatively by the condensation of 2-methylbenzimidazole (4) with benzaldehydes (5a-c) using glycerol as solvent. 2-Styrylbenzimidazoles (3a-c) and 2-methylbenzimidazole (4) were alkylated independently to obtain N-alkyl- 2-styrylbenzimidazole (7a-i) and N-alkyl-2-methylbenzimidazole (6a-c), respectively using DMS/DES/PhCH2Cl applying green methods such as simple physical grinding of reactants in solid phase, treating reactants in PEG-600 as a solvent in solution phase and using microwave irradiation of reactants respectively. Compounds 7a-i could also be prepared, alternatively, by heating 6a-c with 5a-c in glycerol at 180 °C for 3-4 h.

Diheteroarylmethanes. 5. E-Z isomerism of carbanions substituted by 1,3-Azoles: 13C and 15N π-charge/shift relationships as source for mapping charge and ranking the electron-withdrawing power of heterocycles

Previously proposed π-charge/shift relationships have been applied to 13C and 15N shifts of the carbanions of 2-benzylazoles (thiazole, oxazole, and imidazole), their corresponding benzo-fused analogs, and bis(2-azolyl)methanes (azol