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

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

• 93-58-3 benzoic acid methyl ester 
• 75-15-0 carbon disulfide 
• 303109-23-1 benzohydrazide 
• 10364-94-0 1-benzoylimidazole 
• 93-89-0 benzoic acid ethyl ester 
• 65-85-0 benzoic acid 
• 613-94-5 benzoic acid hydrazide 
• 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 
• 3004-42-0 2-Mercapto-5-phenyl-1,3,4-oxadiazole 
• 2231-57-4 Thiocarbohydrazide 
• 38539-87-6 potassium 3-benzoyldithiocarbazinate 

Downstream Products

• 114382-18-2 3-phenyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 39602-82-9 6-methyl-3-phenyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 113486-67-2 7H-6-Amino-3-phenyl-s-triazolo<3,4-b><1,3,4>thiadiazine 
• 111828-01-4 (4-amino-5-phenyl-4H-1,2,4-triazol-3-ylsulphanyl)-methylenenitrile 
• 127399-28-4 4-Amino-5-phenyl-3-(S-phenacyl)mercapto-1,2,4-triazole 
• 1198308-25-6 (E)-4-(4-chlorobenzylideneamino)-5-phenyl-2H-1,2,4-triazole-3(4H)-thione 
• 1198308-24-5 5-phenyl-4-[(E)-(phenylmethylidene)amino]-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 1198308-26-7 (E)-4-(4-hydroxy-3-methoxybenzylideneamino)-5-phenyl-2H-1,2,4-triazole-3(4H)-thione 
• 1293362-42-1 methyl 3-(3-phenyl-5-thioxo-1H-1,2,4-triazol-4-ylimino)cholanate 
• 1334336-05-8 6-(3-(cyclopentyloxy)-4-methoxyphenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 160284-94-6 4-(2-chlorobenzylideneamino)-3-phenyl-1,2,4-triazole-5-thione 
• 327031-10-7 4-(2-hydroxy-3,5-dibromobenzylideneamino)-3-phenyl-1,2,4-triazole-5-thione 

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

Triazole based ratiometric fluorescent probe for Zn2+ and its application in bioimaging

An efficient fluorescent chemosensor 4-((2-hydroxynaphthalen-1-yl) methyleneamino)-3-phenyl-1H-1,2,4-triazole-5(4H)-thione, based on triazole has been designed by condensing 2-hydroxy-1-napthaldehyde with amine, appended to 1,2,4-triazole unit. The probe

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.

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