1964-77-8

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-2-METHYL-1H-BENZIMIDAZOLE is used as a key intermediate in the synthesis of various pharmaceuticals for its potential anti-inflammatory and anti-cancer properties. It aids in the development of drugs that could be effective in treating conditions such as asthma and cancer.
Used in Agrochemical Industry:
In the agrochemical sector, 5-BROMO-2-METHYL-1H-BENZIMIDAZOLE is utilized as a building block in the creation of agrochemicals, potentially contributing to the development of new pesticides or other agricultural chemicals that can enhance crop protection and yield.
Used in Chemical Research:
5-BROMO-2-METHYL-1H-BENZIMIDAZOLE serves as a reagent in organic synthesis and is valuable in chemical research for understanding the structure-activity relationships of benzimidazole-based compounds and for exploring new chemical reactions and synthetic pathways.
Used in Organic Synthesis:
As a reagent in organic synthesis, 5-BROMO-2-METHYL-1H-BENZIMIDAZOLE is employed to facilitate the creation of complex organic molecules, which can be further utilized in various chemical and pharmaceutical applications.

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 
• 108-24-7 acetic anhydride 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 64-19-7 acetic acid 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 23373-04-8 2',4'-dibromoacetanilide 
• 124-42-5 acetamidine hydrochloride 
• 1445-45-0 Trimethyl orthoacetate 
• 875-51-4 4-Bromo-2-nitroaniline 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 95-83-0 4-Chloro-1,2-phenylenediamine 

Downstream Products

• 37814-07-6 1-benzyl-5-bromo-2-methyl-1H-benzoimidazole 
• 1314216-34-6 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole 
• 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 

Relevant academic research and scientific papers

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.

Rhodium catalyzed 2-alkyl-benzimidazoles synthesis from benzene-1,2-diamines and tertiary alkylamines as alkylating agents

Substituted 2-alkyl-benzimidazoles were synthesized from benzene-1,2-diamine and tertiary amines as alkylating agent under polystyrene supported rhodium (Rh@PS) nanoparticles (NPs) catalyzed conditions. The heterogeneous rhodium catalyst was applied first time for the synthesis of 2-alkyl-benzimidazoles. The reaction followed through oxidation of alkylamines, transamination, and oxidative cyclisation with benzene-1,2-diamines for the corresponding products synthesis with good yields. The process is applicable for vast substrate scope, several functional groups are tolerable, and the Rh@PS catalyst is recyclable up to four cycles without significant loss in catalytic activity.

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.

Benzimidazoles and benzothiazoles from styrenes and N-vinylimidazole via palladium catalysed oxidative C[dbnd]C and C[sbnd]N bond cleavage

Herein we report a first, palladium catalyzed, one-pot methodology for the synthesis of pharmacologically important benzimidazoles and benzothiazoles from readily available terminal aromatic olefins. The process involves sequential C[dbnd]C/C[sbnd]N bond cleavage followed by C[sbnd]N/C[sbnd]S bond formation.

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.).

Oxalic/malonic acids as carbon building blocks for benzazole, quinazoline and quinazolinone synthesis

An oxidant, base and metal free methodology has been developed for the synthesis of various 2-substituted and non-substituted benzazoles, quinazolines and quinazolinones using oxalic/malonic acids as an in situ carbon source. This methodology is applicable for a wide range of substituted o-phenylenediamine, o-aminothiophenol, o-aminophenol and o-aminobenzamide containing various functional groups and provides good to excellent yields of the corresponding product. Furthermore an easy workup procedure, high yield and easy isolation of products are key features of this methodology. The developed protocol is also applicable for the gram scale synthesis of benzimidazoles.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

Gadolinium (III) chloride catalyzed facile synthesis of 2-substituted benzimidazoles under solvent-free conditions

A series of 2-substituted benzimidazoles have been prepared from o-diamines and 1,3-dicarbonyl compounds using Gadolinium chloride as a catalyst under solvent free condition in good yields. Gadolinium chloride has been demonstrated as a mild and efficient catalyst.

Synthesis of Mavatrep: A Potent Antagonist of Transient Receptor Potential Vanilloid-1

The process development of Mavatrep (1), a potent transient receptor potential vanilloid-1 (TRPV1) antagonist, is described. The two key synthetic transformations are the synthesis of (E)-6-bromo-2-(4-(trifluoromethyl)styryl)1H-benzo[d]imidazole (4) and the Suzuki coupling of 4 with 3,3-dimethyl-3H-benzo[c][1,2]oxaborol-1-ol (5). Compound 1a was prepared in four chemical steps in 63% overall yield.

Novel fatty acid binding protein 4 (FABP4) inhibitors: Virtual screening, synthesis and crystal structure determination

Fatty acid binding protein 4 (FABP4) is a potential drug target for diabetes and atherosclerosis. For discovering new chemical entities as FABP4 inhibitors, structure-based virtual screening (VS) was performed, bioassay demonstrated that 16 of 251 tested compounds are FABP4 inhibitors, among which compound m1 are more active than endogenous ligand linoleic acid (LA). Based on the structure of m1, new derivatives were designed and prepared, leading to the discovery of two more potent inhibitors, compounds 9 and 10. To further explore the binding mechanisms of these new inhibitors, we determined the X-ray structures of the complexes of FABP4-9 and FABP4-10, which revealed similar binding conformations of the two compounds. Residue Ser53 and Arg126 formed direct hydrogen bonding with the ligands. We also found that 10 could significantly reduce the levels of lipolysis on mouse 3T3-L1 adipocytes. Taken together, in silico, in vitro and crystallographic data provide useful hints for future development of novel inhibitors against FABP4.