255064-10-9

Basic information

• Product Name: 6-BROMO-4-METHYL-1H-BENZOIMIDAZOLE
• Synonyms: 6-BROMO-4-METHYL-1H-BENZOIMIDAZOLE;4-broMo-6-Methyl-1H-benzo[d]iMidazole;6-BroMo-4-Methyl-1H-benzo[d]iMidazole;5-Bromo-7-methyl-1H-benzimidazole;6-bromo-4-methyl-1H-benzimidazole
• CAS NO: 255064-10-9
• Molecular Formula: C₈H₇BrN₂
• Molecular Weight: 211.06
• Product Categories: pharmacetical
• Mol File: 255064-10-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 420.1 °C at 760 mmHg
• Flash Point: 207.9 °C
• Appearance: /
• Density: 1.654 g/cm³
• Vapor Pressure: 7.03E-07mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 6-BROMO-4-METHYL-1H-BENZOIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-4-METHYL-1H-BENZOIMIDAZOLE(255064-10-9)
• EPA Substance Registry System: 6-BROMO-4-METHYL-1H-BENZOIMIDAZOLE(255064-10-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 255064-10-9(Hazardous Substances Data)

Usage

General Description

6-Bromo-4-methyl-1H-benzimidazole is a chemical compound with the molecular formula C8H7BrN2. It is a heterocyclic aromatic compound containing a benzimidazole ring substituted with a bromine atom and a methyl group. This chemical has potential applications in pharmaceutical and agrochemical industries as it exhibits various biological activities. It can be used as a building block in the synthesis of pharmaceuticals, including anti-cancer and anti-inflammatory drugs, as well as fungicides and pesticides. Additionally, it has been researched for its potential as a fluorescent probe in biological imaging and as an inhibitor of protein kinases. Overall, 6-Bromo-4-methyl-1H-benzimidazole is a versatile chemical with wide-ranging applications in various fields.

InChI:InChI=1/C8H7BrN2/c1-5-2-6(9)3-7-8(5)11-4-10-7/h2-4H,1H3,(H,10,11)

Upstream product

• 64-18-6 formic acid 
• 76153-06-5 5-bromo-3-methylbenzene-1,2-diamine 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 4887-83-6 4-methylbenzimidazole 
• 952511-71-6 7-methyl-1H-benzimidazole-5-carbonitrile 
• 398452-96-5 4-methyl-1H-benzo[d]imidazole-6-carboxylic acid 
• 255064-08-5 6-bromo-1H-benzo[d]imidazole-4-carboxylic acid 
• 255064-05-2 6-bromo-7-nitro-1H-benzoimidazole-4-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide 

Relevant articles and documents

FUSED IMIDAZOLE COMPOUNDS

The present invention provides compounds represented by formula (I), pharmaceutically acceptable salts thereof, N-oxides thereof, solvates thereof or prodrugs thereof (wherein the characters are as defined in the description). The compounds represented by formula (I) have affinity and selectivity for the gamma-aminobutyric acid A receptor subunit alpha 5 (GABAA α5) and act as GABAA α5 negative allosteric modulators (GABAA α5 NAM), so that they are useful in the prevention and/or treatment of diseases which are related to the GABAA α5 such as Alzheimer's disease.

Maximizing lipophilic efficiency: The use of Free-Wilson analysis in the design of inhibitors of acetyl-CoA carboxylase

This paper describes the design and synthesis of a novel series of dual inhibitors of acetyl-CoA carboxylase 1 and 2 (ACC1 and ACC2). Key findings include the discovery of an initial lead that was modestly potent and subsequent medicinal chemistry optimization with a focus on lipophilic efficiency (LipE) to balance overall druglike properties. Free-Wilson methodology provided a clear breakdown of the contributions of specific structural elements to the overall LipE, a rationale for prioritization of virtual compounds for synthesis, and a highly successful prediction of the LipE of the resulting analogues. Further preclinical assays, including in vivo malonyl-CoA reduction in both rat liver (ACC1) and rat muscle (ACC2), identified an advanced analogue that progressed to regulatory toxicity studies.

Benzimidazole derivatives. 2. Synthesis and structure-activity relationships of new azabicyclic benzimidazole-4-carboxylic acid derivatives with affinity for serotoninergic 5-HT3 receptors

A new series of azabicyclic benzimidazole-4-carboxamides 2-21 and - carboxylates 22-30 were synthesized and evaluated for binding affinity at serotoninergic 5-HT3 and 5-HT4 receptors in the CNS. Most of the synthesized compounds exhibited high or very high affinity for the 5-HT3 binding site and low to no significant affinity for the 5-HT4 receptor. SAR observations indicated that a halogen atom at the 6-position and a nitro group at the 7-position of the benzimidazole ring is the best substitution pattern for 5-HT3 affinity and 5-HT3/5-HT4 selectivity, as well as no substitution in this ring. (S)-(-)-N-(Quinuclidin-3-yl)benzimidazole-4- carboxamides 2, 8, and 14 bound at central 5-HT3 sites with high affinity (K(i) = 2.6, 0.13, and 1.7 nM, respectively) and excellent selectivity over serotonin 5-HT4 and 5-HT(1A) receptors (K(i) > 1000-10000 nM). Furthermore, these new 5-HT3 receptor ligands were pharmacologically characterized as potent and selective 5-HT3 antagonists in the isolated guinea pig ileum (pA2 = 9.6, 9.9, and 9.1, respectively).