3363-56-2

Usage

Uses

Used in Pharmaceutical Industry:
2,5,6-Trimethylbenzimidazole is used as a research compound for the study of B12-dependent enzymes, which are vital in understanding the biological processes and mechanisms involving vitamin B12.
Used in Biochemical Research:
2,5,6-Trimethylbenzimidazole is used as a key intermediate in the biosynthesis of vitamin B12, aiding in the investigation of the metabolic pathways and the role of vitamin B12 in DNA synthesis and the metabolism of fatty and amino acids.

InChI:InChI=1/C10H12N2/c1-6-4-9-10(5-7(6)2)12-8(3)11-9/h4-5H,1-3H3,(H,11,12)

Upstream product

• 64-19-7 acetic acid 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 1004-36-0 2,6-dimethylpyrone 
• 130081-62-8 3-[1-(2-Amino-4,5-dimethyl-phenylamino)-eth-(E)-ylidene]-dihydro-furan-2-one 
• 63780-37-0 (E)-3-(2-Amino-4,5-dimethyl-phenylamino)-but-2-enoic acid ethyl ester 
• 70254-61-4 4-hydroxy-6-methyl-2H-pyran-2-one 
• 626-53-9 1,3-diacetyl acetone 
• 71-36-3 butan-1-ol 
• 513-86-0 3-hydroxy-2-butanon 
• 1445-45-0 Trimethyl orthoacetate 
• 5396-89-4 benzyl acetoacetate 
• 75-07-0 acetaldehyde 
• 1558-82-3 ethyl N‐cyanoethanimidate 
• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 

Downstream Products

• 351863-12-2 tris(2,5,6-trimethylbenzimidazolyl-1-yl)-1,3,5-triazine 
• 111210-06-1 2,5,6-trimethylbenzimidazole-4,7-dione 
• 104089-94-3 N-[2-((5Z,10Z,14Z,19Z)-20-[2-(2,2-Dimethyl-propionylamino)-phenyl]-10,15-bis-{2-[2-(2,5,6-trimethyl-benzoimidazol-1-yl)-acetylamino]-phenyl}-porphyrin-5-yl)-phenyl]-2,2-dimethyl-propionamide 
• 104070-05-5 N-[2-((1Z,4Z,9Z,15Z)-15-[2-(2,2-Dimethyl-propionylamino)-phenyl]-10,20-bis-{2-[2-(2,5,6-trimethyl-benzoimidazol-1-yl)-acetylamino]-phenyl}-porphyrin-5-yl)-phenyl]-2,2-dimethyl-propionamide 
• 99643-38-6 1,1',3,3',5,5',6,6'-octamethyl-2,2'-spirobi<2,3-dihydro-1H-benzimidazole> 
• 244759-53-3 (E)-5,6-Dimethyl-2-styryl-1H-benzimidazole 
• 1195791-20-8 2,5,6-trimethyl-1-phenyl-1H-benzo[d]imidazole 
• 80827-26-5 1,3-Diphenyl-7,8-dimethylpyrido<1,2-a>benzimidazole 
• 1313402-09-3 1-methanesulphinylmethyl-2,5,6-trimethyl-1H-benzimidazole 

Relevant academic research and scientific papers

Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid

Metal-free catalyzed intermolecular tandem Michael addition/cyclization has been developed for the synthesis of benzo[4,5]imidazo[1,2-a]pyridines from α-bromocinnamaldehyde and 2-substituted benzimidazoles. The reaction promoted by a simple inorganic base displays moderate to good yields and good functional group tolerance. The optical properties of some typical products have been investigated. We found that, due to the presence of the benzene ring at the C1-position of benzo[4,5]imidazo[1,2-a]pyridines which restricts intramolecular motion, as a new type of aggregation-induced emission (AIE) luminogen (AIEgen), they show very good solid-state fluorescence with quantum yields up to 88.80%. Importantly, the AIE performance of compound3bcan be useful to detect the nitroaromatic explosive picric acid (PA) with a detection limit and quenching constant of 42.5 nM and 7.27 × 104M?M, respectively.

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.

"Metal-Free" Nanoassemblies of AIEE-ICT-Active Pyrazine Derivative: Efficient Photoredox System for the Synthesis of Benzimidazoles

Supramolecular nanoassemblies of an AIEE-ICT-active pyrazine derivative (TETPY) having strong absorption in the visible region and excellent transportability have been utilized as an efficient photoredox catalytic system for the synthesis of a variety of benzimidazoles having electron-withdrawing/electron-releasing/aliphatic groups under "metal-free"conditions. The reaction protocol involves the successful harvesting of visible light by TETPY assemblies to catalyze the coupling of o-phenylenediamine/substituted diamines and substituted aromatic/heterocyclic/aliphatic aldehydes under aerial conditions using mixed aqueous media as the reaction solvent. TETPY assemblies could activate aerial oxygen to generate superoxide for completing the vital proton abstraction step without the need for any external metal/base/oxidant. Moreover, all the products are purified by recrystallization from organic solvents. The TETPY assemblies also exhibited high efficiency in catalyzing the synthesis of 2-substituted benzothiazoles and quinazolines in excellent yields.

A benzimidazole and synthetic method of derivative thereof (by machine translation)

The present invention provides a benzimidazole and its derivative synthesis method, the method through the imidazole chloride catalyzed O-phenylenediamine cyclized, realizes the multi-functional chain dibasic and imidazole and 2 - substituted benzimidazole synthesis, method is simple and economic, and the practicability is strong. This invention does not have any other catalyst or additive, synthetic method has good functional group tolerance and excellent yield and purity, reaction time is short, and does not need the harsh reaction conditions, is suitable for industrial production. (by machine translation)

Benzimidazoles as Metal-Free and Recyclable Hydrides for CO2 Reduction to Formate

We report a novel metal-free chemical reduction of CO2 by a recyclable benzimidazole-based organo-hydride, whose choice was guided by quantum chemical calculations. Notably, benzimidazole-based hydride donors rival the hydride-donating abilities of noble-metal-based hydrides such as [Ru(tpy)(bpy)H]+ and [Pt(depe)2H]+. Chemical CO2 reduction to the formate anion (HCOO-) was carried out in the absence of biological enzymes, a sacrificial Lewis acid, or a base to activate the substrate or reductant. 13CO2 experiments confirmed the formation of H13COO- by CO2 reduction with the formate product characterized by 1H NMR and 13C NMR spectroscopy and ESI-MS. The highest formate yield of 66% was obtained in the presence of potassium tetrafluoroborate under mild conditions. The likely role of exogenous salt additives in this reaction is to stabilize and shift the equilibrium toward the ionic products. After CO2 reduction, the benzimidazole-based hydride donor was quantitatively oxidized to its aromatic benzimidazolium cation, establishing its recyclability. In addition, we electrochemically reduced the benzimidazolium cation to its organo-hydride form in quantitative yield, demonstrating its potential for electrocatalytic CO2 reduction. These results serve as a proof of concept for the electrocatalytic reduction of CO2 by sustainable, recyclable, and metal-free organo-hydrides.

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.

Imidazolium chloride-catalyzed synthesis of benzimidazoles and 2-substituted benzimidazoles from o-phenylenediamines and DMF derivatives

A facile, general, and economical synthesis of diversely functionalized benzimidazoles and 2-substituted benzimidazoles has been realized via the imidazolium chloride-catalyzed cyclization of o-phenylenediamines with DMF derivatives. This protocol shows a broad substrate scope for aliphatic, aromatic, and heteroaromatic amides. A series of benzimidazoles and 2-substituted benzimidazoles have been obtained in moderate to excellent yields.

Silica–ferric chloride (SiO2–FeCl3) catalyzed selective synthesis of 2-substituted benzimidazole through Csp2Csp3bond cleavage of β-ketoester/amide

Silica–ferric chloride (SiO2–FeCl3) supported reagent was successfully utilized as recyclable catalyst for the general and highly efficient synthesis of 2-substituted benzimidazole by the condensation of 1,2-diamino benzene and β-ketoester/amide followed by original Csp2Csp3bond cleavage. Evidences in favor of C[sbnd]C (α–β) bond cleavage of β-ketoesters/amides are established.