126651-85-2

Basic information

• Product Name: 5-(3-bromophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• Synonyms: 5-(3-bromophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione;5-(3-bromophenyl)-4H-1,2,4-triazole-3-thiol
• CAS NO: 126651-85-2
• Molecular Formula: C₈H₆BrN₃S
• Molecular Weight: 256.13
• Mol File: 126651-85-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 326.6°C at 760 mmHg
• Flash Point: 151.3°C
• Appearance: /
• Density: 1.83g/cm³
• Vapor Pressure: 0.000214mmHg at 25°C
• Refractive Index: 1.775
• CAS DataBase Reference: 5-(3-bromophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-bromophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione(126651-85-2)
• EPA Substance Registry System: 5-(3-bromophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione(126651-85-2)

Safety Data

• Hazardous Substances Data: 126651-85-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H6BrN3S/c9-6-3-1-2-5(4-6)7-10-8(13)12-11-7/h1-4H,(H2,10,11,12,13)

Upstream product

• 585-76-2 m-bromobenzoic acid 
• 618-89-3 methyl 3-bromobenzoate 
• 39115-96-3 3-bromo-benzoic acid hydrazide 
• 126651-84-1 2-(3-bromobenzoyl)hydrazinecarbothioamide 

Downstream Products

• 1044736-54-0 5-(p-chlorobenzoylmethylmercapto)-3-(m-bromophenyl)-s-triazole hydrobromide 
• 1044736-53-9 5-(p-bromobenzoylmethylmercapto)-3-(m-bromophenyl)-s-triazole hydrobromide 
• 1236188-37-6 1-ferrocenyl-2-(3-(3-bromophenyl)-1H-1,2,4-triazol-5-ylthio)ethanone 
• 1190602-20-0 C₂₄H₂₀Br₂N₈S₂ 

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.

The synthesis, X-ray crystal structure and optical properties of novel 1-ferrocenyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylthio)ethanone derivatives

A series of novel 1-ferrocenyl-2-(3-phenyl-1H-1,2,4-triazol-5-ylthio)ethanone derivatives was synthesized by the reaction of 3-substituted-1H-1,2,4-triazole-5-thiol and chloroacetyl ferrocene in the presence of sodium hydride and potassium iodide at reflux. The structures of the new compounds were determined by IR and 1H NMR spectroscopy and HRMS. The structure of compound 5c was established by X-ray crystallography. UV-vis absorption and fluorescence spectra were recorded in ethanol and dichloromethane. The results showed that compounds 5a-g display similar absorptions ranging from 300 to 500 nm and maximal emission bands are about 566 nm. The intensity of fluorescence and maximal emission bands are dependent on the groups bonded to triazole rings.