6646-70-4

Basic information

• Product Name: (1-BENZYL-1H-BENZIMIDAZOL-2-YL)METHANOL
• Synonyms: (1-benzyl-1H-benzimidazol-2-yl)methanol(SALTDATA: FREE);(1-Benzyl-1H-benzoimidazol-2-yl)-methanol;[1-(benzyl)benzimidazol-2-yl]methanol;[1-(phenylmethyl)-2-benzimidazolyl]methanol;[1-(phenylmethyl)benzimidazol-2-yl]methanol
• CAS NO: 6646-70-4
• Molecular Formula: C₁₅H₁₄N₂O
• Molecular Weight: 238.29
• Mol File: 6646-70-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 466°C at 760 mmHg
• Flash Point: 235.7°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 1.74E-09mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: (1-BENZYL-1H-BENZIMIDAZOL-2-YL)METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1-BENZYL-1H-BENZIMIDAZOL-2-YL)METHANOL(6646-70-4)
• EPA Substance Registry System: (1-BENZYL-1H-BENZIMIDAZOL-2-YL)METHANOL(6646-70-4)

Safety Data

• Hazardous Substances Data: 6646-70-4(Hazardous Substances Data)

Usage

General Description

(1-Benzyl-1H-benzimidazol-2-yl)methanol is a chemical compound with a molecular structure that consists of a benzene ring connected to a benzimidazole ring and a methanol group. It is commonly used in organic synthesis and medicinal chemistry as a building block for the synthesis of various pharmaceuticals and bioactive compounds. (1-BENZYL-1H-BENZIMIDAZOL-2-YL)METHANOL has potential biological activities, including antiviral, antimicrobial, and anticancer properties, making it a valuable tool in drug discovery and development. Additionally, it has been studied for its potential applications in materials science, such as in the development of novel polymers and functional materials. Overall, (1-benzyl-1H-benzimidazol-2-yl)methanol is a versatile and important chemical compound with a wide range of potential applications in various fields.

InChI:InChI=1/C15H14N2O/c18-11-15-16-13-8-4-5-9-14(13)17(15)10-12-6-2-1-3-7-12/h1-9,18H,10-11H2

Upstream product

• 5822-13-9 N-benzyl-1,2-phenylenediamine 
• 4856-97-7 2-(Hydroxymethyl)benzimidazole 
• 95-54-5 1,2-diamino-benzene 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 5729-06-6 N-benzyl-2-nitroaniline 
• 141-46-8 Glycolaldehyde 
• 449796-13-8 N-acetoxy-2-(acetoxymethyl)benzimidazole 
• 33809-91-5 (1H-benzo[d]imidazol-2-yl)methyl acetate 
• 944061-83-0 C₁₇H₁₆N₂O₂ 

Downstream Products

• 180000-91-3 1-benzyl-1H-benzo[d]imidazole-2-carbaldehyde 
• 189560-87-0 4-((1-benzyl-1H-benzo[d]imidazol-2-yl)methyl)piperazine-1-carbaldehyde 
• 7192-00-9 1-benzyl-2-(chloromethyl)-1H-benzo[d]imidazole 
• 1568975-31-4 benzyl 4-((1-benzyl-1H-benzo[d]imidazol-2-yl)methyl)piperazine-1-carboxylate 
• 1211330-70-9 4-((1-benzyl-1H-benzo[d]imidazol-2-yl)methyl)-N-phenylpiperazine-1-carboxamide 
• 1172525-83-5 (4-((1-benzyl-1H-benzo[d]imidazol-2-yl)methyl)piperazin-1-yl)(phenyl)methanone 
• 1172074-20-2 1-benzyl-2-((4-(phenylsulfonyl)piperazin-1-yl)methyl)-1H-benzo[d]imidazole 
• 189560-86-9 1-benzyl-2-(piperazin-1-ylmethyl)-1H-benzo[d]imidazole 

Relevant articles and documents

Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon

D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.

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.

"All-water" chemistry of tandem N-alkylation-reduction- condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles

A water-assisted tandem N-alkylation-reduction-condensation process has been devised as a new synthetic route for the one-pot synthesis of N-arylmethyl-2-substituted benzimidazoles. Water plays the crucial and indispensable role through hydrogen bond mediated 'electrophile-nucleophile dual activation' in promoting selective N-monobenzylation of o-nitroanilines as an alternative to the transition metal-based chemistry for C-N bond formation (amination) and forms the basis of disposing the substituents on the benzimidazole moiety in regiodefined manner. Water also exerts a beneficial effect in the condensation of N-monobenzylated o-phenylenediamines with aldehydes. The water-assisted C-N bond formation chemistry led to metal/base-free synthesis of N-monobenzylated o-nitroanilines and N-monobenzylated o-phenylenediamines. The indispensable/advantageous role of water in the various stage of the N-alkylation-reduction-condensation process exemplifies an 'all-water' chemistry for the synthesis of N-arylmethyl-2- substituted benzimidazoles.