114058-91-2

Basic information

• Product Name: 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL
• Synonyms: CHEMBRDG-BB 4012401;5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL;4H-1,2,4-triazole-3-thiol, 5-(4-fluorophenyl)-;5-(4-fluorophenyl)-4H-1,2,4-triazole-3-thiol(SALTDATA: FREE);2,4-Dihydro-5-(4-fluorophenyl)-3H-1,2,4-triazole-3-thione;3H-1,2,4-Triazole-3-thione, 2,4-dihydro-5-(4-fluorophenyl)-;5-(4-fluorophenyl)-1,2-dihydro-1,2,4-triazole-3-thione;3H-1,2,4-Triazole-3-thione, 5-(4-fluorophenyl)-1,2-dihydro-
• CAS NO: 114058-91-2
• Molecular Formula: C₈H₆FN₃S
• Molecular Weight: 195.22
• Mol File: 114058-91-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 263.2°Cat760mmHg
• Flash Point: 113°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 0.0104mmHg at 25°C
• Refractive Index: 1.707
• CAS DataBase Reference: 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(114058-91-2)
• EPA Substance Registry System: 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL(114058-91-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 114058-91-2(Hazardous Substances Data)

Usage

General Description

5-(4-Fluorophenyl)-4H-1,2,4-triazole-3-thiol is a chemical compound with the molecular formula C9H6FN3S. It is a thiol derivative of 1,2,4-triazole, which is a five-membered aromatic heterocycle with three nitrogen atoms. 5-(4-FLUOROPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL has a fluorophenyl group attached to the 5-position of the triazole ring, giving it specific chemical and biological properties. It is often used as a building block in the synthesis of pharmaceuticals and agrochemicals, and it has also been studied for its potential anti-cancer and anti-bacterial activities. Its molecular structure and properties make it a valuable compound for various research and industrial applications.

InChI:InChI=1/C8H6FN3S/c9-6-3-1-5(2-4-6)7-10-8(13)12-11-7/h1-4H,(H2,10,11,12,13)

Upstream product

• 403-43-0 4-fluorobenzoyl chloride 
• 831-38-9 2-(4-fluorobenzoyl)hydrazinecarbothioamide 
• 456-22-4 4-Fluorobenzoic acid 
• 79-19-6 thiosemicarbazide 
• 403-33-8 methyl 4-flurobenzoate 
• 2714-90-1 phenyl 4-fluorobenzoate 
• 456-06-4 4-fluorobenzoyl hydrazide 

Downstream Products

• 1363773-47-0 3-(4-benzylpiperazino)propyl [5-(4-fluorophenyl)-4H-1,2,4-triazol-3-yl]sulfide 

Relevant articles and documents

Novel panaxadiol triazole derivatives induce apoptosis in HepG-2 cells through the mitochondrial pathway

In this study, we introduced 1, 2, 4-triazole groups into panaxadiol (PD) to obtain 18 panaxadiol triazole derivatives. Five cancer cells and one normal cell were evaluated for cytotoxicity by MTT assay. The results showed that most of the derivatives could inhibit cancer cell proliferation, and the anti-proliferative activity of compound A1 was the most significant. For HepG-2 cells, the IC50 value was 4.21 ± 0.54 μM, which was nearly 15 times higher than the activity of PD. Further studies showed that compound A1 could induce apoptosis in HepG-2 cells, and could enhance the expression of Cl-caspase-3, Cl-caspase-9 and Cl-PARP. Moreover, Western blot analysis showed that after treating HepG-2 cells with compound A1, the expression of p53 protein was increased and the ratio of Bax/Bcl-2 was gradually increased. The cytoplasmic Bax is then translocated to the mitochondria, causing the release of Cyt c protein. Therefore, the results indicate that compound A1 induces apoptosis through the mitochondrial pathway and can be used the potential to develop new anti-proliferative agents.

Discovery of [1,2,4]triazole derivatives as new metallo-β-lactamase inhibitors

The emergence and spread of metallo-β-lactamase (MBL)-mediated resistance to β-lactam antibacterials has already threatened the global public health. A clinically useful MBL inhibitor that can reverse β-lactam resistance has not been established yet. We here report a series of [1,2,4]triazole derivatives and analogs, which displayed inhibition to the clinically relevant subclass B1 (Verona integron-encoded MBL-2) VIM-2. 3-(4-Bromophenyl)-6,7-dihydro-5H-[1,2,4]triazolo [3,4-b][1,3]thiazine (5l) manifested the most potent inhibition with an IC50 (half-maximal inhibitory concentration) value of 38.36 μM. Investigations of 5l against other B1 MBLs and the serine β-lactamases (SBLs) revealed the selectivity to VIM-2. Molecular docking analyses suggested that 5l bound to the VIM-2 active site via the triazole involving zinc coordination and made hydrophobic interactions with the residues Phe61 and Tyr67 on the flexible L1 loop. This work provided new triazole-based MBL inhibitors and may aid efforts to develop new types of inhibitors combating MBL-mediated resistance.

Synthesis and biological evaluation of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione as antimycobacterial agents

Resistance among dormant mycobacteria leading to multidrug-resistant and extremely drug-resistant tuberculosis is one of the major threats. Hence, a series of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione derivatives (4a–5c) have been synthesized and screened for their antitubercular activity against Mycobacterium tuberculosis H37Ra (H37Ra). The triazolethiones 4b and 4v showed high antitubercular activity (both MIC and IC50) against the dormant H37Ra by in vitro and ex vivo. They were shown to have more specificity toward mycobacteria than other Gram-negative and Gram-positive pathogenic bacteria. The cytotoxicity was almost insignificant up to 100?μg/ml against THP-1, A549, and PANC-1 human cancer cell lines, and solubility was high in aqueous solution, indicating the potential of developing these compounds further as novel therapeutics against tuberculosis infection.