23269-10-5

Basic information

• Product Name: 1-BENZYL-1H-IMIDAZOLE-2-THIOL
• Synonyms: 1-BENZYL-2-MERCAPTOIMIDAZOLE
• CAS NO: 23269-10-5
• Molecular Formula: C₁₀H₁₀N₂S
• Molecular Weight: 190.27
• Mol File: 23269-10-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 308.1°Cat760mmHg
• Flash Point: 140.1°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 0.000697mmHg at 25°C
• Refractive Index: 1.696
• CAS DataBase Reference: 1-BENZYL-1H-IMIDAZOLE-2-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYL-1H-IMIDAZOLE-2-THIOL(23269-10-5)
• EPA Substance Registry System: 1-BENZYL-1H-IMIDAZOLE-2-THIOL(23269-10-5)

Safety Data

• Hazardous Substances Data: 23269-10-5(Hazardous Substances Data)

Usage

Chemical Family

Imidazoles

Type of Compound

Sulfur-containing heterocyclic compound

Structural Feature

Benzyl group attached to the imidazole ring

Applications

Corrosion inhibitor in the oil and gas industry
Stabilizer in rubber and plastics
Fungicide
Pharmaceutical intermediate

Properties

Antimicrobial
Antifungal

Usage in Personal Care and Cosmetics

Popular choice for formulation due to antimicrobial and antifungal properties

Additional Uses

Cross-linking agent in polymer production
Catalyst in organic synthesis

Versatility

Wide range of industrial and commercial applications

InChI:InChI=1/C10H10N2S/c13-10-11-6-7-12(10)8-9-4-2-1-3-5-9/h1-7H,8H2,(H,11,13)

Upstream product

• 54879-88-8 N-benzyl-2,2-dimethoxyethylamine 
• 333-20-0 potassium thioacyanate 
• 54879-74-2 (2,2-Dimethoxy-ethyl)-[1-phenyl-meth-(Z)-ylidene]-amine 
• 100-46-9 benzylamine 
• 39123-65-4 3-benzyl-2-thioxotetrahydro-4H-imidazol-4-one 
• 100862-09-7 N-benzyl-N'-(2,2-diethoxy-ethyl)-thiourea 
• 84345-15-3 3-benzyl-2-thioxo-2,3-dihydro-1H-imidazole-4-carboxylic acid 
• 100-52-7 benzaldehyde 
• 622-78-6 Benzyl isothiocyanate 
• 134124-35-9 N-Benzyl-N'-(carboxymethyl)thiourea 
• 61190-10-1 N-benzyl-N-(2,2-diethoxyethyl)amine 
• 540-72-7 sodium thiocyanide 

Downstream Products

• 23269-09-2 1-benzyl-2-(methylsulfanyl)imidazole 
• 4238-71-5 1-benzylimidazole 
• 1026882-42-7 [2-(1-Benzyl-1H-imidazol-2-ylsulfanylmethyl)-phenyl]-dimethyl-amine 
• 5376-10-3 1-benzyl-2-(hydroxymethyl)imidazole 
• 16042-26-5 1-(phenylmethyl)-1H-imidazole-2-carboxylic acid 
• 511534-88-6 sodium bis(2-mercapto-1-benzylimidazolyl)borate 
• 511534-80-8 mercury(II) bis(2-mercapto-1-benzylimidazolyl)borate 
• 511534-78-4 zinc(II) bis(2-mercapto-1-benzylimidazolyl)borate 
• 511534-79-5 cadmium(II) bis(2-mercapto-1-benzylimidazolyl)borate 

Relevant articles and documents

Facile conversion of amino acids into 1-alkyl imidazole-2-thiones, and their oxidative desulfurization to imidazoles with benzoyl peroxide

Glycine was acylated with isothiocyanates and condensed to 3-alkyl 2-thiohydantoins, which were reduced with a mixture of sodium borohydride and lithium chloride and dehydrated to 1-alkyl imidazole-2-thiones. These were oxidatively desulfurized to imidazoles with benzoyl peroxide. No chromatography was required for model compounds. The methods developed were used to elaborate tyrosine to 1,4-di(p-methoxybenzyl)imidazole, a common intermediate in the syntheses of three imidazoles from the sponge Leucetta. Georg Thieme Verlag Stuttgart.

2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6- tetrahydrocyclopent[d]imidazoles as a novel class of gastric H+/K+-ATPase inhibitors

Substituted 2-sulfinylimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K+-ATPase. The 4,5-unsubstituted imidazole series 6-11 and the 1,4,5,6-tetrahydrocyclopent[d]imidazole series 12 were found to be potent inhibitors of the acid secretory enzyme H+/K+- ATPase. Structure-activity relationships indicate that the substitution of 2- pyridyl groups at the 1-position of the imidazole moiety combined with (2- aminobenzyl)sulfinyl groups at the 2-position leads to highly active compounds with a favorable chemical stability. Other substitution patterns in the imidazole moiety result in reducing biological activities. 2-[(2- Aminobenzyl)sulfinyl]-1-[2-(3-methylpyridyl)]-1,4,5,6- tetrahydrocyclopent[d]imidazole (12h, T-776) was selected for further development as a potential clinical candidate. Extensive study on the acid degradation of 12h indicates a mechanism of action different from that of omeprazole, the first H+/K+-ATPase inhibitor introduced to the market.

Multisubstrate inhibitors of dopamine β-hydroxylase. 1. Some 1-phenyl and 1-phenyl-bridged derivatives of imidazole-2-thione

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