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

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

Uses

Used in Pharmaceutical Industry:
4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL is used as a drug development candidate for its antimicrobial, antifungal, and antiviral properties, contributing to the creation of new treatments for various infections and diseases.
Used in Organic Synthesis and Chemical Research:
4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL is utilized as a building block in organic synthesis, enabling the development of complex organic molecules and facilitating chemical research in various domains.
Used in Food Industry:
4-ETHYL-5-PHENYL-1,2,4-TRIAZOLE-3-THIOL is used as a potential antioxidant in food preservatives and additives, helping to extend the shelf life of food products and maintain their quality.

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 
• 613-94-5 benzoic acid hydrazide 
• 93-58-3 benzoic acid methyl ester 

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

Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity

New N-4-piperazinyl ciprofloxacin-triazole hybrids 6a-o were prepared and characterized. The in vitro antimycobacterial activity revealed that compound 6a experienced promising antimycobacterial activity against Mycobactrium smegmatis compared with the reference isoniazide (INH). Additionally, compound 6a exhibited broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative bacteria compared with the reference ciprofloxacin. Also, compounds 6g and 6i displayed considerable antifungal activity compared with the reference ketoconazole. DNA cleavage assay of the highly active compounds 6c and 6h showed a good correlation between the Mycobactrium cleaved DNA gyrase assay and their in vitro antimycobactrial activity. Moreover, molecular modeling studies were done for the designed ciprofloxacin derivatives to predict their binding modes towards Topoisomerase II enzyme (PDB: 5bs8).

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.

1,2,4-Triazole/oxime hybrids as new strategy for nitric oxide donors: Synthesis, anti-inflammatory, ulceroginicity and antiproliferative activities

A series of novel nitric oxide (NO) donating triazole/oxime hybrids was prepared and evaluated for their anti-inflammatory activity and antiproliferative activity. Most of the tested compounds showed significant anti-inflammatory activity using carrageenan-induced rat paw edema method compared to indomethacin. Calculation of the ulcer indices and histopathological investigation indicated that the prepared NO-donating oximes exhibited less ulcerogenicity compared to their ketone intermediates and indomethacin. The NO-donating oximes 7i and 7k achieved remarkable cell growth inhibition activity against most of the tested cell lines. Compound 7k was found to be with high selectivity against CNS subpanel with selectivity ratio of 11.99 at GI 50 level.

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.

New nitric oxide donating 1,2,4-triazole/oxime hybrids: Synthesis, investigation of anti-inflammatory, ulceroginic liability and antiproliferative activities

A series of novel nitric oxide (NO) donating triazole/oxime hybrids was prepared and evaluated for their anti-inflammatory activity. Most of the tested compounds showed significant anti-inflammatory activity using carrageenan-induced rat paw edema method compared to indomethacin. Calculation of the ulcer indices and histopathological investigation indicated that the prepared NO-donating oximes exhibited less ulcerogenicity compared to their intermediate ketones and indomethacin. The NO-donating oxime 6i revealed significant activity against renal cancer A498 cell lines with 50.52 cell growth inhibition.

Synthesis and tuberculostatic activity of some 2-piperazinmethylene derivatives 1,2,4-triazole-3-thiones

The Mannich reaction's products of 1,2,4-triazole-3-thiones, substituted in position 4 (with ethyl, allyl, phenyl, Ph-4-Br) or 5 (with phenyl, Ph-4-OH, Ph-3,4,5-(OMe)3, 2-phenyl) were obtained. Their amino-components were 1-phenylpiperazine, 1-

The reactions of cyclization of thiosemicarbazide derivatives to 1,2,4-triazole or 1,3,4-thiadiazole system

In the reaction of hydrazide of formic, nicotinic and benzoic acid with isothiocyanates were obtained the respective thiosemicarbazide derivatives [I-XII]. Further cyclization with 2% NaOH solution led to formation of derivatives Δ2-1,2,4-triaz