6528-83-2

Usage

Class of compound

Benzimidazole derivative (heterocyclic organic compound)

Core structure

1H-benzimidazole

Substituent

3-methylphenyl group attached at the 2-position

Applications

Pharmaceutical, agrochemical, and materials science industries (due to diverse biological activities and versatile chemical reactivity)

Potential uses

Drug development, building block in organic synthesis

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 99-04-7 m-Toluic acid 
• 88-74-4 2-nitro-aniline 
• 620-23-5 m-tolyl aldehyde 
• 51-17-2 benzoimidazole 
• 591-17-3 meta-bromotoluene 
• 500131-50-0 N,N-diethyl-α,α-difluoro-(meta-methylbenzyl)amine 
• 134-62-3 N,N-Diethyl-3-methylbenzamide 
• 1711-06-4 3-Methylbenzoyl chloride 
• 1042161-50-1 C₁₄H₁₂N₄ 
• 14625-59-3 N-phenyl-2-(3-methylphenyl)formamidine 
• 1224442-23-2 3-methyl-N-(2-nitrophenyl)benzene carboximidamide 
• 620-22-4 3-Methylbenzonitrile 
• 62-53-3 aniline 

Downstream Products

• 79881-94-0 2-m-Tolyl-1-vinyl-1H-benzoimidazole 
• 1135618-14-2 C₁₆H₁₇N₂⁽¹⁺⁾*I^(1-) 
• 1281987-94-7 2-(3-(phenyIthiomethyl)phenyl)-1H-benzo[d]imidazole 
• 1281987-95-8 2-(3-((4-chlorophenylthio)methyI)phenyl)-1H-benzo[d]imidazole 
• 1281987-98-1 2-(3-((4-nitrophenoxy)methyl)phenyl)-1H-benzo[d]imidazole 
• 1281988-01-9 2-(3-(phenoxymethyl)phenyl)-1H-benzo[d]imidazole 
• 1281988-03-1 2-(3-((2-nitrophenoxy)methyl)phenyI)-1H-benzo[d]imidazole 
• 1281987-62-9 tert-butyl 2-m-tolyl-1H-benzo[d]imidazole-1-carboxylate 
• 1281987-68-5 tert-butyl 2-(3-(bromomethyl)phenyl)-1H-benzo[d]imidazole-1-carboxylate 
• 1417819-06-7 2-methyl-6-phenylbenzo[4,5]imidazo[2,1-a]isoquinoline 
• 1417819-08-9 4-methyl-6-phenylbenzo[4,5]imidazo[2,1-a]isoquinoline 

Relevant academic research and scientific papers

Synthesis and evaluation of 2-aryl-1H-benzo[d]imidazole derivatives as potential microtubule targeting agents

Microtubule targeting agents (MTAs) are the potential drug candidates for anticancer drug discovery. Disrupting the microtubule formation or inhibiting the de-polymerization process by a synthetic molecule can lead to an excellent anticancer drug candidat

An Unexpected Formation of 2-Arylbenzimidazoles from α,α-Diiodo-α’-acetoxyketones and o-Phenylenediamines

An unusual reactivity of the α,α-diiodo-α’-acetoxyketones with o-phenylenediamines is reported through the formation of 2-arylbenzimidazoles. A systematic study through a series of fruitful control experiments and isolation of key intermediates unravelled the unprecedented domino mechanism. This process involves a stepwise two-carbon fragmentation pathway through domino and sequential amidation–aziridination–decarbonylation–I2-mediated aminative cyclization–oxidation reactions. This strategy employs no additives like oxidant, metal catalyst, bases, and represents yet another novel reactivity profile of the building blocks α,α-diiodo-α’-acetoxyketones.

Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite

Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.

Method for catalytically synthesizing phenylbenzimidazole compound by using copper complex

The invention relates to a method for catalytically synthesizing a phenylbenzimidazole compound by using a copper complex, which comprises the following steps: in the presence of alkali, taking benzimidazole and halogenated hydrocarbon as raw materials, taking the copper complex containing meta-carborane ligand as a catalyst, and conducting reacting at room temperature to prepare the phenylbenzimidazole compound. Compared with the prior art, the method has the advantages that the halogenated hydrocarbon compound which is low in cost and easy to obtain is used as the substrate, the reaction of benzimidazole and halogenated hydrocarbon is efficiently catalyzed by using the copper complex, the phenylbenzimidazole compound is synthesized by a one-pot method, the reaction condition is mild, the universality is good, the catalytic efficiency is high, few byproducts are produced, the cost is relatively low, the product is easy to separate, and lots of waste residues cannot be generated.

Preparation method of 2-substituted benzimidazole compound

The invention discloses a preparation method of a 2-substituted benzimidazole compound, and belongs to the field of synthesis of benzimidazole compounds. The 2-substituted benzimidazole compound is synthesized in an organic solvent by taking an o-nitroaniline compound, aromatic aldehyde, o-dinitrobenzene and aromatic aldehyde as raw materials and taking Co particles wrapped by a nitrogen-doped carbon material as a catalyst. According to the method, the 2-substituted benzimidazole compound can be prepared at room temperature, the reaction conditions are mild, the yield is as high as 95%, the selectivity is as high as 99%, and the method is economical, environmentally friendly and wide in substrate applicability. The used catalyst is easy to prepare, low in cost and good in reusability, canbe separated by utilizing magnetism, and is convenient to recover, so that the method has a relatively strong industrial application prospect.

Visible-Light Photoredox Catalyzed Double C-H Functionalization: Radical Cascade Cyclization of Ethers with Benzimidazole-Based Cyanamides

A visible-light photoredox catalyzed radical cascade cyclization of simple ethers with cyanamides is developed at room temperature. This strategy involves sequential inert Csp3-H/Csp2-H functionalizations through intermolecular addition reaction of oxyalkyl radicals to N-cyano groups followed by radical cyclization of iminyl radicals in situ generated with C-2 aryl rings. This method allows for efficient synthesis of tetracyclic benzo[4,5]imidazo[1,2-c]quinazolines. Importantly, this is the first example of an intermolecular-intramolecular radical cascade cyclization reaction of cyanamides.

H2 Activation with Co Nanoparticles Encapsulated in N-Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles

Co nanoparticles (NPs) encapsulated in N-doped carbon nanotubes (Co@NC900) are systematically investigated as a potential alternative to precious Pt-group catalysts for hydrogenative heterocyclization reactions. Co@NC900 can efficiently catalyze hydrogenative coupling of 2-nitroaniline to benzaldehyde for synthesis of 2-phenyl-1H-benzo[d]imidazole with >99 % yield at ambient temperature in one step. The robust Co@NC900 catalyst can be easily recovered by an external magnetic field after the reaction and readily recycled for at least six times without any evident decrease in activity. Kinetic experiments indicate that Co@NC900-promoted hydrogenation is the rate-determining step with a total apparent activation energy of 41±1 kJ mol?1. Theoretical investigations further reveal that Co@NC900 can activate both H2 and the nitro group of 2-nitroaniline. The observed energy barrier for H2 dissociation is only 2.70 eV in the rate-determining step, owing to the presence of confined Co NPs in Co@NC900. Potential industrial application of the earth-abundant and non-noble transition metal catalysts is also explored for green and efficient synthesis of heterocyclic compounds.

Al2O3/CuI/PANI nanocomposite catalyzed green synthesis of biologically active 2-substituted benzimidazole derivatives

This work is generally focused on the synthesis of an efficient, reusable and novel heterogeneous Al2O3/CuI/PANI nanocatalyst, which has been well synthesized by a simple self-assembly approach where aniline is oxidized into PANI and

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen

The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.

Method for preparing N - heterocyclic ring through visible light mediated dehydrogenation

The invention discloses a method for preparing N - heterocyclic rings through visible light mediated dehydrogenation, and the reaction can be carried out under the conditions of room temperature and visible light without heating. The novel tetra-coordination N-N - diaryl chelating borate compound serves as a photocatalyst, so that the use of a noble metal photocatalyst is avoided, precious metal residue in the reaction product can be reduced as much as possible, and the method is more suitable for synthesizing bioactive molecules.