64310-34-5

Basic information

• Product Name: 3-(4-METHYLPHENYL)-1H-1,2,4-TRIAZOLE-5-THIOL
• Synonyms: 4H-3-MERCAPTO-5(P-TOLYL)-[1,2,4]TRIAZOLE;5-P-TOLYL-4H-1,2,4-TRIAZOLE-3-THIOL;3-(4-METHYLPHENYL)-1H-1,2,4-TRIAZOLE-5-THIOL;ASISCHEM C34659;TIMTEC-BB SBB000300;4H-1,2,4-triazole-3-thiol, 5-(4-methylphenyl)-;5-(4-methylphenyl)-1,2-dihydro-1,2,4-triazole-3-thione;5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• CAS NO: 64310-34-5
• Molecular Formula: C₉H₉N₃S
• Molecular Weight: 191.25
• Mol File: 64310-34-5.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 282.1°C at 760 mmHg
• Flash Point: 124.4°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 0.00343mmHg at 25°C
• Refractive Index: 1.703
• CAS DataBase Reference: 3-(4-METHYLPHENYL)-1H-1,2,4-TRIAZOLE-5-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-METHYLPHENYL)-1H-1,2,4-TRIAZOLE-5-THIOL(64310-34-5)
• EPA Substance Registry System: 3-(4-METHYLPHENYL)-1H-1,2,4-TRIAZOLE-5-THIOL(64310-34-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 64310-34-5(Hazardous Substances Data)

Usage

General Description

3-(4-Methylphenyl)-1H-1,2,4-triazole-5-thiol is a chemical compound with the molecular formula C9H8N4S. It is a member of the triazole family, which are known for their diverse range of biological and pharmaceutical activities. This particular compound is a thiol derivative of 1,2,4-triazole, which suggests it may have unique chemical properties and potential applications. Thiol compounds are known for their strong odors and reactivity, making them useful in various chemical reactions and industrial processes. Further research is needed to fully understand the properties and potential applications of 3-(4-Methylphenyl)-1H-1,2,4-triazole-5-thiol.

InChI:InChI=1/C9H9N3S/c1-6-2-4-7(5-3-6)8-10-9(13)12-11-8/h2-5H,1H3,(H2,10,11,12,13)

Upstream product

• 96134-00-8 C₁₁H₁₅N₃OS 
• 43002-64-8 ethyl 4-methylbenzimidate hydrochloride 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 99-94-5 p-Toluic acid 
• 3619-22-5 p-toluic hydrazide 
• 13229-01-1 4-amino-2,4-dihydro-5-(4-methylphenyl)-3H-1,2,4-triazole-3-thione 
• 874-60-2 4-methyl-benzoyl chloride 
• 79-19-6 thiosemicarbazide 
• 120449-42-5 Se-phenyl 4-methylbenzenecarboselenothioate 
• 1079-82-9 1-(p-methylbenzoyl)-3-thisemicarbazide 
• 1448538-29-1 4-benzyl-3-(4-methylphenyl)-5-(phenylsulfanyl)-4H-1,2,4-triazole 
• 3335-25-9 4-methylthiobenzoyl chloride 
• 16794-68-6 4-methylbenzoyl isothiocyanate 

Downstream Products

• 87219-99-6 1-(4-Nitro-phenyl)-2-(5-p-tolyl-4H-[1,2,4]triazol-3-ylsulfanyl)-ethanone 
• 219716-05-9 5-[1-(4-Nitro-phenyl)-meth-(Z)-ylidene]-2-p-tolyl-thiazolo[3,2-b][1,2,4]triazol-6-one 
• 132895-44-4 5-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-2-p-tolyl-thiazolo[3,2-b][1,2,4]triazol-6-one 
• 1190602-19-7 C₂₆H₂₆N₈S₂ 
• 1276032-79-1 5-p-methylphenyl-3-(β-D-glucopyranosylthio)-1,2,4-triazole 
• 1276032-69-9 5-p-methylphenyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)-1,2,4-triazole 
• 1363773-39-0 3-[4-(3-chlorophenyl)piperazino]propyl[5-(4-methylphenyl)-4H-1,2,4-triazol-3-yl] sulfide 
• 1363773-41-4 3-(4-ethylpiperazino)propyl [5-(4-methylphenyl)-4H-1,2,4-triazol-3-yl]sulfide 
• 1351946-06-9 C₁₃H₁₈N₄S 
• 1351946-07-0 C₁₅H₂₂N₄S 
• 1351946-08-1 C₂₃H₃₄N₄S 
• 1620200-70-5 diethyl (3-((5-(p-tolyl)-1H-1,2,4-triazol-3-yl)thio)propyl)phosphonate 
• 66953-48-8 5-(prop-2-yn-1-ylthio)-3-(p-tolyl)-1H-1,2,4-triazole 
• 1514931-13-5 2-{[5-(4-methylphenyl)-1H-1,2,4-triazol-3-yl]sulfanyl}acetohydrazide 

Relevant articles and documents

Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction

Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.

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.

Design, synthesis, and negative inotropic evaluation of 4-phenyl-1H-1,2,4-triazol-5(4H)-one derivatives containing triazole or piperazine moieties

In this study, four novel series of 4-phenyl-1H-1,2,4-triazol-5(4H)-one derivatives containing triazole or piperazine moieties were designed, synthesized, and evaluated for negative inotropic activity by measuring the left atrium stroke volume in isolated rabbit heart preparations. Almost all of the compounds showed an ability to moderate the cardiac workload by decreasing the heart rate and contractility. Among them, 7h was found to be the most potent with a change in stroke volume of ?48.22?±?0.36% at a concentration of 3?×?10?5?mol/L (metoprolol: ?9.74?±?0.14%). The cytotoxicity of these compounds was evaluated using the human cervical cancer cell line HeLa, the liver cancer cell line Hep3B, and the human normal hepatic cell line LO2. A preliminary study of the mechanism of action for the compound 7h on the regulation of atrial dynamics with ATP-sensitive K+ channel and L-type Ca2+ channel blockers glibenclamide and nifedipine was performed in the isolated perfused beating rabbit atria.