3363-56-2

Basic information

• Product Name: 2,5,6-TRIMETHYLBENZIMIDAZOLE
• Synonyms: 2,5,6-TRIMETHYLBENZIMIDAZOLE;2,5,6-TRIMETHYL-1H-1,3-BENZIMIDAZOLE;2,5,6-TRIMETHYL-1H-BENZIMIDAZOLE;2,5,6-Trimethylbenzimidazole 98%;1H-Benzimidazole,2,5,6-trimethyl-(9CI)
• CAS NO: 3363-56-2
• Molecular Formula: C₁₀H₁₂N₂
• Molecular Weight: 160.22
• EINECS: 222-130-9
• Product Categories: BENZIMIDAZOLE;Imidazol&Benzimidazole
• Mol File: 3363-56-2.mol
• Article Data: 30

Chemical Properties

• Melting Point: 239-240 °C(lit.)
• Boiling Point: 367.5 °C at 760 mmHg
• Flash Point: 194.8 °C
• Appearance: /
• Density: 1.113 g/cm³
• Vapor Pressure: 2.87E-05mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: 2,5,6-TRIMETHYLBENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5,6-TRIMETHYLBENZIMIDAZOLE(3363-56-2)
• EPA Substance Registry System: 2,5,6-TRIMETHYLBENZIMIDAZOLE(3363-56-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 3363-56-2(Hazardous Substances Data)

Usage

General Description

2,5,6-Trimethylbenzimidazole, also known as 5,6-dimethylbenzimidazole or 5,6-DMB, is a chemical compound that forms as an intermediate in the biosynthesis process of vitamin B12 which is also known as cobalamin. It is acknowledged as the lower ligand, which is the base attached to the cobalt atom in cobalamin. The chemical itself does not possess any nutritional benefit but takes part in an essential biological process as being involved in the production of vitamin B12, which is pivotal in the regulation of DNA synthesis and metabolism of fatty and amino acids. Scientific spheres incorporate this compound for the study of B12-dependent enzymes.

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 
• 141-82-2 malonic acid 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 127-19-5 N,N-dimethyl acetamide 
• 121-44-8 triethylamine 
• 78-39-7 Triethyl orthoacetate 
• 1558-82-3 ethyl N‐cyanoethanimidate 
• 75-07-0 acetaldehyde 
• 5396-89-4 benzyl acetoacetate 
• 1445-45-0 Trimethyl orthoacetate 
• 513-86-0 3-hydroxy-2-butanon 

Downstream Products

• 351863-12-2 tris(2,5,6-trimethylbenzimidazolyl-1-yl)-1,3,5-triazine 
• 80827-26-5 1,3-Diphenyl-7,8-dimethylpyrido<1,2-a>benzimidazole 
• 1195791-20-8 2,5,6-trimethyl-1-phenyl-1H-benzo[d]imidazole 
• 1313402-09-3 1-methanesulphinylmethyl-2,5,6-trimethyl-1H-benzimidazole 
• 244759-53-3 (E)-5,6-Dimethyl-2-styryl-1H-benzimidazole 
• 99643-38-6 1,1',3,3',5,5',6,6'-octamethyl-2,2'-spirobi<2,3-dihydro-1H-benzimidazole> 
• 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 
• 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 
• 111210-06-1 2,5,6-trimethylbenzimidazole-4,7-dione 

Relevant articles and documents

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.

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.

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)