22706-11-2

Basic information

• Product Name: 4-AMINO-5-PHENYL-4H-1,2,4-TRIAZOLE-3-THIOL
• Synonyms: RARECHEM BG FB 0106;IFLAB-BB F0311-0776;BUTTPARK 9\07-04;ASISCHEM V00530;AKOS BBS-00004177;AKOS TOT-0017;4-AMINO-5-PHENYL-4H-1,2,4-TRIAZOL-3-YL HYDROSULFIDE;4-AMINO-5-PHENYL-4H-1,2,4-TRIAZOLE-3-THIOL
• CAS NO: 22706-11-2
• Molecular Formula: C₈H₈N₄S
• Molecular Weight: 192.24
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Triazoles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 22706-11-2.mol
• Article Data: 98

Chemical Properties

• Melting Point: 195 °C (dec.)(lit.)
• Boiling Point: 309.4 °C at 760 mmHg
• Flash Point: 140.9 °C
• Appearance: /
• Density: 1.47 g/cm³
• Vapor Pressure: 0.000643mmHg at 25°C
• Refractive Index: 1.762
• PKA: 8.49±0.20(Predicted)
• CAS DataBase Reference: 4-AMINO-5-PHENYL-4H-1,2,4-TRIAZOLE-3-THIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-5-PHENYL-4H-1,2,4-TRIAZOLE-3-THIOL(22706-11-2)
• EPA Substance Registry System: 4-AMINO-5-PHENYL-4H-1,2,4-TRIAZOLE-3-THIOL(22706-11-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 22706-11-2(Hazardous Substances Data)

Usage

Preparation

Synthesis of 4[amino]-5-phenyl-4H-1,2,4-triazole-3-thiol: A suspension of potassium salt dithiocarbazinate (4.44g, 0.02M), hydrazine hydrate (2ml, 0.04M) and water (80ml) was refluxed for 3 hrs. The color of the reaction mixture changed to green, hydrogen sulphide was evolved and a homogenous solution resulted. A white solid was precipitated by dilution with cold water (100ml) and acidification with concentrated hydrochloric acid. The product was filtered, washed with cold water (2×30 ml) and recrystallised from ethanol in 42 % yield. Melting point : 198 -200°C.IR (KBr cm-1): 943 (N-C-S str), 1278 (N-N-C str), 3365(N-H str), 696 (C-S str), 3082 (Ar CH str), 1446 (C-N str). NMR (ppm): 7.7 (m, 5H, Ar-H), 7.9 (s, 2H, NH2), 14.6(s, 1H, S-H).

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 13, p. 925, 1976 DOI: 10.1002/jhet.5570130450The Journal of Organic Chemistry, 47, p. 2757, 1982 DOI: 10.1021/jo00135a014

InChI:InChI=1/C8H8N4S/c9-12-7(10-11-8(12)13)6-4-2-1-3-5-6/h1-5H,9H2,(H,11,13)

Upstream product

• 3004-42-0 5-phenyl-1,3,4-oxadiazole-2(3H)-thione 
• 2231-57-4 Thiocarbohydrazide 
• 65-85-0 benzoic acid 
• 93-89-0 benzoic acid ethyl ester 
• 75-15-0 carbon disulfide 
• 613-94-5 benzoic acid hydrazide 
• 7449-45-8 methyl N'-benzoylhydrazinocarbodithioate 
• 93-58-3 benzoic acid methyl ester 
• 303109-23-1 benzohydrazide 
• 10364-94-0 1-benzoylimidazole 
• 74-88-4 methyl iodide 
• 3291-03-0 3,4,5-trimethoxybenzohydrazide 
• 6178-44-5 ethyl 3,4,5-trimethoxybenzoate 
• 31821-78-0 3-(3,4,5-trimetossifenil)-4-ammino-5-mercapto-4H-1,2,4-triazolo 

Downstream Products

• 139268-04-5 6-<5-(4-Nitrophenyl)-2-furyl>-3-phenyl-1,2,4-triazolo<3,4-b>-1,3,4-thiadiazole 
• 79074-74-1 3,6,7-Triphenyl-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 39573-67-6 4-amino-3-methylthio-5-phenyl-1,2,4-triazole 
• 132635-78-0 4-Amino-2-methyl-5-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 178384-10-6 1,2-bis(4-amino-5-phenyl-3-ylsulfanyl)ethane 
• 261156-03-0 4-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-ylmethylene)-amino]-5-phenyl-4H-[1,2,4]triazole-3-thiol 
• 263900-72-7 1,4-bis(4-amino-5-phenyl-1,2,4-triazol-3-ylsulfanyl)butane 
• 341520-13-6 4-Amino-3-allylthio-5-phenyl-4H-1,2,4-triazole 
• 341520-14-7 4-Amino-3-(2-methylprop-2-enyl)thio-5-phenyl-4H-1,2,4-triazole 
• 109194-49-2 N¹-phenyl-N³-(3-mercapto-5-phenyl)-1,2,4-triazol-4-yl thiourea 
• 113486-75-2 6-phenylamino-3-phenyl-1,2,4-triazolo<3,4-b><1,3,4>thiadiazole 
• 111828-18-3 Benzoic acid N'-[2-(4-amino-5-phenyl-4H-[1,2,4]triazol-3-ylsulfanyl)-acetyl]-hydrazide 
• 32476-07-6 4-benzoylamino-5-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 68469-07-8 6-(4-nitrophenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 

Relevant articles and documents

Synthesis and antibacterial activity of oxime ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety

A series of oxime ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety were designed and synthesized, and their antibacterial activities in vitro against Xanthomonas axonopodis pv. citri (Xac) and Xanthomonas oryzae pv. oryzae (Xoo) were

Identification of Novel Class of Triazolo-Thiadiazoles as Potent Inhibitors of Human Heparanase and their Anticancer Activity

Background: Expression and activity of heparanase, an endoglycosidase that cleaves heparan sulfate (HS) side chains of proteoglycans, is associated with progression and poor prognosis of many cancers which makes it an attractive drug target in cancer therapeutics. Methods: In the present work, we report the in vitro screening of a library of 150 small molecules with the scaffold bearing quinolones, oxazines, benzoxazines, isoxazoli(di)nes, pyrimidinones, quinolines, benzoxazines, and 4-thiazolidinones, thiadiazolo[3,2-a]pyrimidin-5-one, 1,2,4-triazolo-1,3,4-thiadiazoles, and azaspiranes against the enzymatic activity of human heparanase. The identified lead compounds were evaluated for their heparanase-inhibiting activity using sulfate [35S] labeled extracellular matrix (ECM) deposited by cultured endothelial cells. Further, anti-invasive efficacy of lead compound was evaluated against hepatocellular carcinoma (HepG2) and Lewis lung carcinoma (LLC) cells. Results: Among the 150 compounds screened, we identified 1,2,4-triazolo-1,3,4-thiadiazoles bearing compounds to possess human heparanase inhibitory activity. Further analysis revealed 2,4-Diiodo-6-(3-phenyl-[1, 2, 4]triazolo[3,4-b][1, 3, 4]thiadiazol-6yl)phenol (DTP) as the most potent inhibitor of heparanase enzymatic activity among the tested compounds. The inhibitory efficacy was demonstrated by a colorimetric assay and further validated by measuring the release of radioactive heparan sulfate degradation fragments from [35S] labeled extracellular matrix. Additionally, lead compound significantly suppressed migration and invasion of LLC and HepG2 cells with IC50 value of ~5 μM. Furthermore, molecular docking analysis revealed a favourable interaction of triazolo-thiadiazole backbone with Asn-224 and Asp-62 of the enzyme. Conclusions: Overall, we identified biologically active heparanase inhibitor which could serve as a lead structure in developing compounds that target heparanase in cancer.

Synthesis, characterization, and anticancer activity of some azole-heterocyclic complexes with gold(III), palladium(II), nickel(II), and copper(II) metal ions

Four new complexes of Au(III), Pd(II), Ni(II), and Cu(II) ions were synthesized, derived from a novel heterocyclic ligand (L) that has both triazole and tetrazole rings. The ligand synthesis was through successive steps to achieve both heterocyclic rings.

Anionic ligands tune the structural and catalytic properties of quinoxaline-based copper(II) complexes as mimetics of copper-containing oxidase protein

The hexadentate ligand containing quinoxaline backbone along with its Cu(II) -based complexes with various anionic ligands were synthesized and their structures were determined. Molecular formulae were assigned based on the data of both elemental analysis

Efficient Synthesis of Fluorinated [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazoles

Abstract: An efficient synthesis of fluorinated [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives has been achievedby cyclocondensation of 5-substituted 4-amino-1,2,4-triazole-3-thiols withfluoro-substituted aromatic acids using phosphoryl chloride as a cyclizingagent. The synthesized compounds were characterized by spectroscopic techniques,including IR, 1H NMR, and mass spectra.