24425-13-6

Basic information

• Product Name: 2-TERT-BUTYLBENZIMIDAZOLE
• Synonyms: AKOS BBS-00004644;AKOS BB-3173;2-TERT-BUTYL-1H-BENZIMIDAZOLE;2-TERT-BUTYLBENZIMIDAZOLE;2-T-BUTYLBENZIMIDAZOLE;TIMTEC-BB SBB003800;2-tert-butyl-benzimidazol;1H-Benzimidazole,2-(1,1-dimethylethyl)-(9CI)
• CAS NO: 24425-13-6
• Molecular Formula: C₁₁H₁₄N₂
• Molecular Weight: 174.24
• Product Categories: BENZIMIDAZOLE;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines
• Mol File: 24425-13-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 320 °C
• Boiling Point: 295.23°C (rough estimate)
• Flash Point: 166.6°C
• Appearance: /
• Density: 1.076
• Vapor Pressure: 0.00017mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-TERT-BUTYLBENZIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-TERT-BUTYLBENZIMIDAZOLE(24425-13-6)
• EPA Substance Registry System: 2-TERT-BUTYLBENZIMIDAZOLE(24425-13-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 24425-13-6(Hazardous Substances Data)

Usage

Chemical Properties

purple needle-like crystalline powder

InChI:InChI=1/C11H14N2/c1-11(2,3)10-12-8-6-4-5-7-9(8)13-10/h4-7H,1-3H3,(H,12,13)

Upstream product

• 150783-31-6 2,2-dimethyl-2'-nitropropananilide 
• 88-74-4 2-nitro-aniline 
• 3282-30-2 pivaloyl chloride 
• 862898-39-3 N-(2-diphenylacetylaminophenyl)-2,2-dimethylpropionamide 
• 615-42-9 1,2-Diiodobenzene 
• 59950-56-0 pivalimidamide 

Downstream Products

• 111198-31-3 2-(1,1,-dimethylethyl)-1-(phenylthiomethyl)benzimidazole 
• 111198-47-1 2-(1,1-dimethylethyl)-1-<2-phenyl-1-(phenylthio)-ethyl>benzimidazole 

Relevant articles and documents

Synthesis of benzimidazoles by phosphine-mediated reductive cyclisation of ortho-nitro-anilides

Heating ortho-nitro-anilides 1-3 and 2-methyl-N-(3-nitropyridin-2-yl) propanamide (5) with 4 equiv. of a phosphine led to the 2-substituted benzimidazoles 6-8 and to the imidazo[4,5-b]pyridine 10, respectively, in yields between 45 and 85%. Heating 1 with (EtO)3P effected cyclisation and N-ethylation, leading to the 1-ethylbenzimidazole 6b. The slow cyclisation of the N-pivaloylnitroaniline 2b allowed isolation of the intermediate phosphine imide 11 that slowly transformed into the 1H-benzimidazole 7b. The structure of 11 was established by crystal-structure analysis. While the N-methylated ortho-nitroacetanilide 3 cyclised to the 1,2-dimethyl-1H-benzimidazole (8), the 2-methylpropananilide 4 was transformed into 1-methyl-3-(1-methylethyl)-2H- benzimidazol-2-one (9).

Conversion of sterically hindered diacylated 1,2-phenylenediamines into 2-substituted benzimidazoles

A series of bulky 2-substituted benzimidazoles was designed in order to find new leads for several biological targets. Formation by cyclodehydration from their monoacylated counterparts was shown to be strongly dependent upon the nature of the acyl group. In the case of a dicyclohexylmethyl group, cycllzation was only observed in a p-toluenesulfonic acid/toluene mixture from the symmetrical diacylated precursor. Analysis of the mechanism was begun starting from mixed diacylated derivatives.