21541-32-2

Basic information

• Product Name: 2H-Benzimidazole-2-thione,1-acetyl-1,3-dihydro-(9CI)
• Synonyms: 2H-Benzimidazole-2-thione,1-acetyl-1,3-dihydro-(9CI);1-Acetyl-1,3-dihydrobenziMidazole-2-thione;2-Mercapto-1-acetylbenziMidazole;1-(2-sulfanylidene-3H-benzimidazol-1-yl)ethanone
• CAS NO: 21541-32-2
• Molecular Formula: C₉H₈N₂OS
• Molecular Weight: 192.23762
• Product Categories: BENZIMIDAZOLE
• Mol File: 21541-32-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Benzimidazole-2-thione,1-acetyl-1,3-dihydro-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Benzimidazole-2-thione,1-acetyl-1,3-dihydro-(9CI)(21541-32-2)
• EPA Substance Registry System: 2H-Benzimidazole-2-thione,1-acetyl-1,3-dihydro-(9CI)(21541-32-2)

Safety Data

• Hazardous Substances Data: 21541-32-2(Hazardous Substances Data)

Usage

Class of Compound

Benzimidazole

Structure

Benzene ring fused to an imidazole ring
Thione group attached at position 2
Acetyl group at position 1
Dihydro group at position 3

Applications

Organic synthesis
Pharmaceutical research

Usage

Building block for drug development
Active pharmaceutical ingredient

Potential Applications

Treatment of various diseases and medical conditions

Properties

Chemical properties: Reactivity due to functional groups
Biological properties: Potential therapeutic effects
Physical properties: Melting point, solubility, etc.

Behaviors

Reactivity in different reaction conditions
Pharmacological behaviors in biological systems

Upstream product

• 3042-01-1 thiazolo[3,2-a]benzimidazol-3(2H)-one 
• 108-24-7 acetic anhydride 
• 134469-07-1 Benzimidazol-2-thiol 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 56029-79-9 N,N'-Diacetyl-benzimidazolin-2-thion 
• 137213-71-9 (triphenylmethyl)sulfanylbenzimidazole 
• 137213-76-4 1-(2-Tritylsulfanyl-benzoimidazol-1-yl)-ethanone 

Downstream Products

• 878991-07-2 C₂₁H₁₉N₅O₂S₂ 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 51290-77-8 2-(benzylthio)-1H-benzo[d]imidazole 

Relevant articles and documents

Synthesis and crystal structures of benzimidazole-2-thione derivatives by alkylation reactions

Alkylated, benzylated and bromoalkylated benzimidazole-thione that intramolecularly heterocyclized to 3,4-dihydro-2H-[1,3]thiazino[3,2-a]benzimidazole were synthesized. The chemical structure of the synthesized product was characterized by Infra Red, 1H-NMR, 13C-NMR, and Mass spectroscopy. Furthermore, the molecular structures of 8 and 9 were confirmed by X-ray single crystallography in different space groups, Pbca and P21/c, respectively.

Inhibitors of the salicylate synthase (Mbti) from Mycobacterium tuberculosis discovered by high-throughput screening

A simple steady-state kinetic high-throughput assay was developed for the salicylate synthase MbtI from Mycobacterium tuberculosis, which catalyzes the first committed step of mycobactin biosynthesis. The mycobactins are small-molecule iron chelators produced by M. tuberculosis, and their biosynthesis has been identified as a promising target for the development of new antitubercular agents. The assay was miniaturized to a 384-well plate format and high-throughput screening was performed at the National Screening Laboratory for the Regional Centers of Excellence in Biodefense and Emerging Infectious Diseases (NSRB). Three classes of compounds were identified comprising the benzisothiazolones (class I), diarylsulfones (class II), and benzimidazole-2-thiones (class III). Each of these compound series was further pursued to investigate their biochemical mechanism and structure-activity relationships. Benzimidazole-2-thione 4 emerged as the most promising inhibitor owing to its potent reversible inhibition.

Synthesis of N-substituted benzimidazole-2-thiones

General methods were developed for N-substitution of benzimidazoline-2-thione with alkyl, alkenyl, alkynyl and acyl groups using S-tritylation as a protecting reaction.