1964-77-8

Basic information

• Product Name: 5-BROMO-2-METHYL-1H-BENZIMIDAZOLE
• Synonyms: 5-BROMO-2-METHYL-1H-BENZIMIDAZOLE;5-BROMO-2-METHYL-1H-BENZO[D]IMIDAZOLE;5-BROMO-2-METHYLBENZIMIDAZOLE;5-BROMO-2-METHYL-1H-BENZ(D)IMIDAZOLE;5-Bromo-2-methylbenzoimidazole;1H-BenziMidazole, 6-broMo-2-Methyl-;5-broMo-2-Methyl-1H-1,3-benzodiazole;5-Bromo-2-methyl-1H-benzoimidazole
• CAS NO: 1964-77-8
• Molecular Formula: C₈H₇BrN₂
• Molecular Weight: 211.06
• Mol File: 1964-77-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 214-215 °C
• Boiling Point: 397.3 °C at 760 mmHg
• Flash Point: 194.1 °C
• Appearance: /
• Density: 1.654 g/cm³
• Vapor Pressure: 3.66E-06mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.50±0.10(Predicted)
• CAS DataBase Reference: 5-BROMO-2-METHYL-1H-BENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-METHYL-1H-BENZIMIDAZOLE(1964-77-8)
• EPA Substance Registry System: 5-BROMO-2-METHYL-1H-BENZIMIDAZOLE(1964-77-8)

Safety Data

• Hazardous Substances Data: 1964-77-8(Hazardous Substances Data)

Usage

General Description

5-Bromo-2-methyl-1H-benzimidazole is a chemical compound with the molecular formula C8H6BrN2. It is a benzimidazole derivative with a bromine atom attached to the 5-position and a methyl group at the 2-position. 5-BROMO-2-METHYL-1H-BENZIMIDAZOLE is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. It is known for its potential anti-inflammatory and anti-cancer properties, and it has been studied for its potential use in the treatment of diseases such as asthma and cancer. 5-Bromo-2-methyl-1H-benzimidazole is also used in chemical research and as a reagent in organic synthesis.

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

Upstream product

• 881-50-5 N-(4-bromo-2-nitrophenyl)acetamide 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 105919-36-6 trans-4-(trifluoromethyl)cinnamoyl chloride 
• 64-19-7 acetic acid 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 121-44-8 triethylamine 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 1072-63-5 1-vinylimidazole 
• 141-97-9 ethyl acetoacetate 
• 875-51-4 4-Bromo-2-nitroaniline 
• 64-17-5 ethanol 
• 141-82-2 malonic acid 

Downstream Products

• 37814-07-6 1-benzyl-5-bromo-2-methyl-1H-benzoimidazole 
• 1300585-33-4 2-(1-(4-amino-3-(2-methyl-1H-benzo[d]imidazol-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one 
• 1189544-30-6 2-chloro-5-(2-methyl-3H-benzoimidazole-5-carbonyl)-benzenesulfonamide 
• 1314216-34-6 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole 

Relevant articles and documents

Visible light initiated oxidative coupling of alcohols ando-phenylenediamines to synthesize benzimidazoles over MIL-101(Fe) promoted by plasmonic Au

The use of visible light to initiate one-pot synergistic/cascade reactions is a green and energy saving strategy. In this manuscript, we report that MIL-101(Fe) can act as a multifunctional catalyst to realize the oxidative condensation betweeno-phenylenediamines and alcohols to synthesize benzimidazoles under visible light. The deposition of plasmonic Au nanoparticles (Au NPs) on MIL-101(Fe) led to significantly improved activity. Both controlled experiments and electron spin resonance (ESR) results revealed that the production of benzimidazoles fromo-phenylenediamines and alcohols involves three sequential steps,i.e., the oxidative dehydrogenation of alcohols to produce aldehydes, the condensation betweeno-phenylenediamines and the aldehydes to produce Schiff bases and their oxidation to form benzimidazoles,viaa superoxide radical (O2˙?)-mediated pathway. The promoting effect of plasmonic Au NPs in this reaction can be ascribed to the effective transfer of the surface plasmon resonance (SPR)-excited hot electrons to the lowest unoccupied molecular orbital (LUMO) of MIL-101(Fe), which led to the generation of more active O2˙?radicals. This study not only provides a green and sustainable way for the synthesis of benzimidazoles, but also highlights the great potential of using rationally designed plasmonic metal NP/MOF nanocomposites as multifunctional catalysts for light initiated one-pot tandem/cascade reactions.

Sustainable photocatalytic synthesis of benzimidazoles

Among the 17 Sustainable Development Goals presented by the United Nations in 2015, great attention is devoted to the production of goods and chemicals by use of renewable raw materials, by recycling of products and by extensive use of renewable energy sources. In this context, photocatalysis attracted great attention for the possibility to exploit Solar light to promote the desired chemical reactions. Besides its use in degradation of pollutants and in the production of fuels, some efforts have been devoted in the development of photocatalytic processes for the synthesis of fine chemicals with high added-value. In this work, we investigated the sustainable photocatalytic synthesis of benzimidazole derivatives through a one-pot, tandem process starting from a nitro compound and ethanol. By a photocatalytic approach, ethanol is dehydrogenated producing the hydrogen required for reduction of nitro groups and the aldehyde required for cyclization and production of the benzimidazole unit. Co-doping of TiO2 with B and N is beneficial to increase the photocatalytic activity in H2 production from ethanol. The effect of various metal co-catalysts (Pt, Pd Ag, Cu) have been evaluated on H2 production rate and on selectivity in the synthesis of substituted benzimidazoles: Pt showed the highest selectivity in the desired products while Pd demonstrated a great activity for hydrodehalogenation, with potential interest for degradation of persistent pollutants.

Supported Rhodium (Rh@PS) Catalyzed Benzimidazoles Synthesis Using Ethanol/Methanol as C2H3/CH Source

An effective and stable polystyrene supported rhodium (Rh@PS) nano-catalyst has been synthesized by following reduction-deposition approach and applied for the selective benzimidazoles synthesis from 1,2-phenylenediamines and ethanol/methanol as C2H3/CH source. The ethanol/methanol in the presence of trace amounts of aerobic oxygen under Rh@PS catalysed condition, first participated in oxidation of alcohol followed by consecutive condensation, cyclization and hydrogen elimination reactions with 1,2-phenylenediamine gave the desired products in good yields. The Rh@PS catalyst in a single system performed both oxidation and reduction reactions in a selective/specific manner and applied for large substrate scope. Easy recovery, handling, stability, recyclability of the catalyst and less chance of metal contamination with the products are the added advantages of the process. (Figure presented.).