180000-91-3

Basic information

• Product Name: 1-BENZYL-1H-BENZOIMIDAZOLE-2-CARBALDEHYDE
• Synonyms: 1-(PHENYLMETHYL)-1H-BENZIMIDAZOLE-2-CARBOXALDEHYDE;1-BENZYL-1H-BENZOIMIDAZOLE-2-CARBALDEHYDE;1-BENZYL-1H-BENZIMIDAZOLE-2-CARBALDEHYDE;1-(benzyl)benzimidazole-2-carbaldehyde;1-(phenylmethyl)-2-benzimidazolecarboxaldehyde;1-(phenylmethyl)benzimidazole-2-carbaldehyde;1-benzyl-1H-benzo[d]imidazole-2-carbaldehyde
• CAS NO: 180000-91-3
• Molecular Formula: C15H12N2O
• Molecular Weight: 236.27
• Mol File: 180000-91-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 450.8 °C at 760 mmHg
• Flash Point: 226.4 °C
• Appearance: /
• Density: 1.17 g/cm³
• Vapor Pressure: 2.56E-08mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: 1-BENZYL-1H-BENZOIMIDAZOLE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYL-1H-BENZOIMIDAZOLE-2-CARBALDEHYDE(180000-91-3)
• EPA Substance Registry System: 1-BENZYL-1H-BENZOIMIDAZOLE-2-CARBALDEHYDE(180000-91-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 180000-91-3(Hazardous Substances Data)

Usage

General Description

1-BENZYL-1H-BENZOIMIDAZOLE-2-CARBALDEHYDE is a chemical compound with a molecular formula C15H12N2O. It is an aldehyde derivative of benzimidazole and is used in the synthesis of various pharmaceuticals and organic compounds. This chemical possesses an aromatic benzene ring attached to a benzimidazole ring, with a benzyl group and a carbonyl group in its structure. It is commonly utilized as a reagent in organic chemistry reactions, and its versatile properties make it a valuable building block in the production of biologically active compounds and pharmaceuticals.

InChI:InChI=1/C15H12N2O/c18-11-15-16-13-8-4-5-9-14(13)17(15)10-12-6-2-1-3-7-12/h1-9,11H,10H2

Upstream product

• 4981-92-4 1-benzylbenzimidazole 
• 68-12-2 N,N-dimethyl-formamide 
• 51-17-2 benzoimidazole 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 95-54-5 1,2-diamino-benzene 
• 6646-70-4 (1-benzyl-1H-benzo[d]imidazol-2-yl)methanol 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 5805-83-4 1-benzyl-2-methylbenzimidazole 

Downstream Products

• 1456686-53-5 (E)-3-(1-benzyl-1H-benzimidazol-2-yl)-2-cyanoprop-2-ene-thioamide 
• 62209-30-7 1-benzyl-2-hydroxyiminomethylbenzimidazole 
• 312631-73-5 1-benzyl-2-iodo-1H-benzo[d]imidazole 

Relevant articles and documents

Metal-free oxidative decarbonylative halogenation of fused imidazoles

An efficient strategy has been developed for the deformylative halogenation of carbaldehyde imidazo-fused heterocycles in the presence of TBHP controlled by temperature. A convenient and sequential functionalization (C8 to C3) portrays the synthetic utility of the current method.N-Heterocycle benzamide products were also observedviathe ring opening of imidazopyridines through the cleavage of C-C bond at high temperatures. Features of this method include temperature-controlled excellent regioselectivity, mild conditions and functional group tolerance.

Design, synthesis and biological evaluation of benzimidazole-rhodanine conjugates as potent topoisomerase II inhibitors

In this study, a series of benzimidazole-rhodanine conjugates were designed, synthesized and investigated for their topoisomerase II (Topo II) inhibitory and cytotoxic activities. The results from Topo II-mediated pBR322 DNA relaxation and cleavage assays showed that the synthesized compounds might act as Topo II catalytic inhibitors. Certain compounds displayed potent Topo II inhibition at 10 μM. The cytotoxic activities of these compounds against HeLa, A549, Raji, PC-3, MDA-MB-201, and HL-60 cancer cell lines were evaluated. The results indicated that these compounds exhibited strong antiproliferative activity. A good relationship was observed between the Topo II inhibitory potency and the cytotoxicity of these compounds. The structure-activity relationship revealed that the electronic effects, the phenyl group, and the rhodanine moiety were particularly important for the Topo II inhibitory potency and cytotoxicity.

Mechanochemical and conformational study of N-heterocyclic carbonyl-oxime transformations

New mechanochemical pathways for the transformation of six N-heterocyclic carbonyl compounds into oximes using hydroxylamine hydrochloride were explored. Reactions were performed first without any base since the heterocyclic moieties (imidazole, benzimidazole, pyridine and quinuclidine) have an intrinsic basic nitrogen atom. This green, solvent free method was suitable for all compounds (up to quantitative yields) except for N-benzyl substituted imidazole and benzimidazole-2-carbaldehyde. For the slower reacting aldehydes, reactions with liquid assisted grinding and addition of sodium hydroxide were performed as well. Conformational analysis and quantum-chemical calculations revealed steric and electronic reasons for the lower reactivity of N-benzyl substituted derivatives.