26131-61-3

Basic information

• Product Name: 4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL
• Synonyms: 4-ETHYL-5-PHENYL-4 H-[1,2,4]TRIAZOLE-3-THIOL;4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL;4-ETHYL-5-PHENYL-4H-1,2,4-TRIAZOL-3-YLHYDROSULFIDE;AKOS BBS-00003283;CHEMBRDG-BB 3017964;ASISCHEM V63434;ART-CHEM-BB B017964;TIMTEC-BB SBB009417
• CAS NO: 26131-61-3
• Molecular Formula: C₁₀H₁₁N₃S
• Molecular Weight: 205.28
• Mol File: 26131-61-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 286.6 °C at 760 mmHg
• Flash Point: 127.1 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 0.00261mmHg at 25°C
• Refractive Index: 1.659
• Storage Temp.: 2-8°C
• PKA: 8.36±0.20(Predicted)
• CAS DataBase Reference: 4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL(26131-61-3)
• EPA Substance Registry System: 4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL(26131-61-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 26131-61-3(Hazardous Substances Data)

Usage

General Description

4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL is a chemical compound with the molecular formula C11H10N4S. It is a derivative of triazole with an ethyl and phenyl group attached to the carbon 4 and 5 positions, and a thiol group attached to the carbon 3 position. 4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL has potential applications in the pharmaceutical industry, particularly in the development of new drugs with antimicrobial, antifungal, and antiviral properties. It is also used as a building block in organic synthesis and chemical research. Additionally, 4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL may possess antioxidant properties, making it a potential candidate for use in food preservatives and additives. Overall, this compound has a diverse range of potential applications and is of interest to researchers and industries in various fields.

InChI:InChI=1/C10H11N3S/c1-2-13-9(11-12-10(13)14)8-6-4-3-5-7-8/h3-7H,2H2,1H3,(H,12,14)

Upstream product

• 26257-93-2 2-benzoyl-N-ethylhydrazinecarbothioamide 
• 65-85-0 benzoic acid 
• 93-89-0 benzoic acid ethyl ester 
• 93-58-3 benzoic acid methyl ester 
• 613-94-5 benzoic acid hydrazide 

Downstream Products

• 485334-41-6 2-(4-ethyl-5-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl)-1-phenylethanone 
• 121112-25-2 2-(4-Ethyl-3-phenyl-5-thioxo-4,5-dihydro-[1,2,4]triazol-1-yl)-N-(2-methyl-4-oxo-4H-quinazolin-3-yl)-acetamide 

Relevant articles and documents

An investigation of supramolecular synthons in 1,2,4-triazole-3(4H)-thione compounds. X-ray crystal structures, energetic and Hirshfeld surface analysis

A series of four closely related 1,2,4-triazole-3-thione (1-4) compounds was obtained by heterocyclization of thiosemicarbazides under basic catalytic conditions. The crystal structures of the 4-alkyl-5-(substituted-phenyl)-2H-1,2,4-triazole-3(4H)-thione

Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β- d -ribofuranose 2′-Oxidase

We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure-activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H37Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 μM, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-β-d-ribofuranose 2′-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.

Synthesis and invitro Evaluation of West Nile Virus Protease Inhibitors Based on the 2-{6-[2-(5-Phenyl-4H-{1,2,4]triazol-3-ylsulfanyl)acetylamino]benzothiazol-2-ylsulfanyl}acetamide Scaffold

In recent years, clinical symptoms resulting from West Nile virus (WNV) infection have worsened in severity, with an increased frequency in neuroinvasive diseases among the elderly. As there are presently no successful therapies against WNV for use in humans, continual efforts to develop new chemotherapeutics against this virus are highly desired. The viral NS2B-NS3 protease is a promising target for viral inhibition due to its importance in viral replication and its unique substrate preference. In this study, a WNV NS2B-NS3 protease inhibitor with a 2-{6-[2-(5-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl)acetylamino]benzothiazol-2-ylsulfanyl}acetamide scaffold was identified during screening. Optimization of this initial hit by synthesis and screening of a focused compound library with this scaffold led to the identification of a novel uncompetitive inhibitor (1a24, IC50=3.4±0.2μM) of the WNV NS2B-NS3 protease. Molecular docking of 1a24 into the WNV protease showed that the compound interferes with productive interactions of the NS2B cofactor with the NS3 protease and is an allosteric inhibitor of the WNV NS3 protease.