2963-65-7

Usage

Uses

Used in Pharmaceutical Industry:
5-METHYL-2-PHENYL-1H-BENZO[D]IMIDAZOLE is used as a pharmaceutical candidate for its potential medicinal properties. It has shown to exhibit anti-cancer, anti-inflammatory, and anti-microbial effects, making it a promising compound for the development of new drugs to treat various diseases and conditions.
Used in Cancer Treatment:
In the field of oncology, 5-METHYL-2-PHENYL-1H-BENZO[D]IMIDAZOLE is used as an anti-cancer agent. Its potential to target and inhibit the growth of cancer cells has positioned it as a candidate for further research and development in cancer treatment.
Used in Anti-Inflammatory Applications:
5-METHYL-2-PHENYL-1H-BENZO[D]IMIDAZOLE is utilized as an anti-inflammatory agent due to its ability to reduce inflammation. This property makes it a candidate for the treatment of various inflammatory conditions and diseases.
Used in Anti-Microbial Applications:
In the realm of microbiology, 5-METHYL-2-PHENYL-1H-BENZO[D]IMIDAZOLE is employed as an anti-microbial agent. Its effectiveness against certain microorganisms suggests potential use in the development of new antimicrobial drugs to combat infections.
Used in Drug Development:
5-METHYL-2-PHENYL-1H-BENZO[D]IMIDAZOLE is used in the research and development of new pharmaceutical drugs. Its unique structural features and demonstrated biological activities make it a valuable compound for creating innovative and effective medications.

Upstream product

• 5467-06-1 N,N'-(4-methyl-o-phenylene)-bis-benzamide 
• 111273-17-7 4-(4-methylphenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-one 
• 53476-33-8 2'-amino-4'-methylbenzanilide 
• 857616-89-8 acetic acid-(2-benzylidenamino-4-methyl-anilide) 
• 871896-93-4 N-benzoyl-5-methyl-1,2-phenylenediamine 
• 100-52-7 benzaldehyde 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 636-24-8 4-Methyl-benzene-1,2-diamine; hydrochloride 
• 100-47-0 benzonitrile 
• 65-85-0 benzoic acid 
• 36954-12-8 N-(3-methylphenyl)-benzylamine oxime 
• 98-09-9 benzenesulfonyl chloride 
• 36298-61-0 3-phenyl-4-benzylideneisoxazol-5(4H)-one 
• 1859-00-3 N-(4-methylphenyl)benzamidine 

Downstream Products

• 24781-11-1 1-benzyl-6-methyl-2-phenyl-1H-benzo[d]imidazole 
• 66630-70-4 2-phenyl-1H-1,3-benzimidazole-5-carboxylic acid 
• 1313401-96-5 5-methyl-1-methylsulphanylmethyl-2-phenyl-1H-benzimidazole 
• 1313402-11-7 5-methyl-1-methanesulphinylmethyl-2-phenyl-1H-benzimidazole 

Relevant academic research and scientific papers

AN EFFICIENT PREPARATION OF 4-ARYLMETHYLISOXAZOL-5-ONES BY SELECTIVE REDUCTION OF THE 4-ARYLMETHYLENEISOXAZOL-5-ONES

An efficient selective reduction of the exocyclic double bond of the 4-arylmethyleneisoxazol-5-ones with o-phenylenediamines and aldehydes is described. 4-arylmethylisoxazol-5-ones are produced in high yields together with comparable quantities of benzimidazoles.

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.

1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles

In the present study, 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride-supported Ni@zeolite-Y-based nanoporous materials (Ni@zeolite-Im-IL) were synthesized and their structures were confirmed using different characterization techniques such as FT-IR, FE-SEM, EDX, XRD, BET and TGA-DTG analyses. In order to synthesize this multi-functional nano-system, zeolite-NaY was modified first, with exchanged Ni2+ ions and 3-chloropropyltriethoxysilane (CPTES) as a coupling reagent and then functionalized to imidazolium chloride ionic liquid by N-methylimidazole. New multi-functional nano-material of Ni@zeolite-Im-IL demonstrated high activity in the catalytic synthesis of 2-aminothiazoles 3a–l by one-pot reaction of methylcarbonyls, thiourea and iodine at 80?°C in DMSO with good to excellent yields (85–98%). Also, the catalytic synthesis of 2-aryl benzimidazoles, 6a–m was performed by the condensational reaction of o-arylendiamine and aromatic aldehydes in EtOH at room temperature with excellent yields (90–98%). Advantages of this efficient synthetic strategy include higher purity and shorter reaction time, excellent yield, easy isolation of products, the good stability, activity and feasible reusability of the metallic ionic liquid nanocatalyst. These benefits have made this method more compatible with the principles of green chemistry. Graphical abstract: [Figure not available: see fulltext.]

One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles

It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.

Nickel catalyzed sustainable synthesis of benzazoles and purines: Via acceptorless dehydrogenative coupling and borrowing hydrogen approach

Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.

Transition-Metal-Free Transfer Hydrogenative Cascade Reaction of Nitroarenes with Amines/Alcohols: Redox-Economical Access to Benzimidazoles

This report describes an efficient transition-metal-free process toward the transfer hydrogenative cascade reaction between nitroarenes and amines or alcohols. The developed redox-economical approach was realized using a combination of KOtBu and Et3SiH as reagents, which allows the synthesis of benzimidazole derivatives via σ-bond metathesis. The reaction conditions hold well over a wide range of substrates embedded with diverse functional groups to deliver the desired products in good to excellent yields. The mechanistic proposal has been depicted on the basis of a series of control experiments, mass spectroscopic evidence which is well supported by density functional theory (DFT) calculations with a feasible energy profile.

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.

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.

Cobalt ferrite magnetic nanoparticles as highly efficient catalyst for the mechanochemical synthesis of 2-aryl benzimidazoles

A highly efficient magnetically separable nano cobalt ferrite catalyst was synthesized via the sol-gel auto combustion method, characterized by powder XRD, SEM, TEM, UV–Visible, FT-IR, magnetic study, and BET isotherm analysis. The synthesized material was found to be an efficient heterogeneous Lewis acid catalyst for the synthesis of 2-aryl benzimidazole derivatives via solvent-free mechanochemical synthesis. The notable features of this new protocol include solvent-free reaction, cost-effectiveness, good yields, and environmental friendliness to afford the products within a short reaction time along with easy recovery and reuse of the nano catalyst.