4922-98-9

Basic information

• Product Name: 5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE
• Synonyms: 3-AMINO-5-PHENYL-1,2,4-TRIAZOLE;5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE;5-PHENYL-1H-[1,2,4]TRIAZOL-3-YLAMINE;2-fenil-5-amino-1,3,4-triazolo;3-amino-5-phenyl-1h-1,2,4-triazole;4-triazol-3-amine,5-phenyl-1h-2;4-triazole,3-amino-5-phenyl-1h-2;2-Fenil-5-amino-1,3,4-triazolo [Italian]
• CAS NO: 4922-98-9
• Molecular Formula: C₈H₈N₄
• Molecular Weight: 160.18
• Mol File: 4922-98-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 191-193℃
• Boiling Point: 276.07°C (rough estimate)
• Flash Point: 233.7 °C
• Appearance: /
• Density: 1.315±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 4.48E-07mmHg at 25°C
• Refractive Index: 1.5872 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 10.78±0.40(Predicted)
• CAS DataBase Reference: 5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE(4922-98-9)
• EPA Substance Registry System: 5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE(4922-98-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 4922-98-9(Hazardous Substances Data)

Usage

Uses

5-Phenyl-4h-1,2,4-triazol-3-amine, is an intermediate in the synthesis of WP155. 5-Phenyl-4h-1,2,4-triazol-3-amine is also used in biological studies to evaluate its pharmacological activity as it can be applied to a method for reducing susceptibility to tumor formation induced by 3-deoxyglucosone and precursors thereof.

Safety Profile

Reaction with nitrous acid gives atouch sensitive explosive product. Upon decomposition itemits toxic fumes of NOx.

InChI:InChI=1/C8H8N4/c9-8-10-7(11-12-8)6-4-2-1-3-5-6/h1-5H,(H3,9,10,11,12)

Upstream product

• 5442-13-7 thiobenzimidic acid ethyl ester; hydrochloride 
• 10308-82-4 aminoguanidine nitrate 
• 3679-92-3 N-(benzamido)-guanidine 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 613-94-5 benzoic acid hydrazide 
• 1186228-45-4 N-methyl-N-(5-phenyl-1,2,4-oxadiazol-3-yl)hydrazine 
• 1257878-79-7 3-hydroxylamino-5-phenyl-1,2,4-triazole 
• 23432-93-1 3-chloro-5-phenyl-1,2,4-oxadiazole 
• 7788-14-9 5-phenyl-1,2,4-oxadiazol-3-amine 
• 3201-50-1 3-Methoxy-5-phenyl-1,2,4-oxadiazole 
• 81677-09-0 3-dimethylamino-5-phenyl-1,2,4-oxadiazole 
• 32252-82-7 1-chloro-1,4-diphenyl-2,3-diazabutadiene 

Downstream Products

• 74258-83-6 3-{1-[(Z)-5-Phenyl-2H-[1,2,4]triazol-3-ylimino]-ethyl}-dihydro-furan-2-one 
• 168893-24-1 5-Amino-1-[methylamino(thiocarbonyl)]-3-phenyl-1H-1,2,4-triazole 
• 1227417-79-9 5-(chloromethyl)-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one 
• 1227417-80-2 C₁₃H₁₀N₄O₃ 
• 1227418-25-8 C₁₂H₇ClF₂N₄O 
• 1227415-58-8 C₂₁H₂₀N₄O 
• 1227415-59-9 C₂₁H₂₀N₄O₂ 
• 1227416-03-6 C₂₁H₂₀N₄O 
• 1227416-05-8 C₂₀H₁₇ClN₄O₂ 
• 1344724-46-4 C₁₈H₁₆N₄O 
• 1344724-45-3 C₁₈H₁₆N₄O₂ 
• 1344724-44-2 C₁₇H₁₃ClN₄O 
• 1344724-52-2 C₁₇H₁₃N₅O₃ 
• 930569-97-4 C₁₅H₁₂N₄O₂ 

Relevant articles and documents

A Novel Iron-catalyzed One-pot Synthesis of 3-Amino-1,2,4-triazoles

A novel one-pot synthesis of 3-amino-1,2,4-triazole developed via iron (III) catalyzed route is reported. The new method is more efficient, simple, and convenient and presents a concise new strategy for the synthesis of 3-amino-1,2,4-triazole derivatives.

Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.

Acylated 1 H-1,2,4-Triazol-5-Amines Targeting Human Coagulation Factor XIIa and Thrombin: Conventional and Microscale Synthesis, Anticoagulant Properties, and Mechanism of Action

We herein report the conventional and microscale parallel synthesis of selective inhibitors of human blood coagulation factor XIIa and thrombin exhibiting a 1,2,4-Triazol-5-Amine scaffold. Structural variations of this scaffold allowed identifying derivative 21i, a potent 29 nM inhibitor of FXIIa, with improved selectivity over other tested serine proteases and also finding compound 21m with 27 nM inhibitory activity toward thrombin. For the first time, acylated 1,2,4-Triazol-5-Amines were proved to have anticoagulant properties and the ability to affect thrombin-And cancer-cell-induced platelet aggregation. Performed mass spectrometric analysis and molecular modeling allowed us to discover previously unknown interactions between the synthesized inhibitors and the active site of FXIIa, which uncovered the mechanistic details of FXIIa inhibition. Synthesized compounds represent a promising starting point for the development of novel antithrombotic drugs or chemical tools for studying the role of FXIIa and thrombin in physiological and pathological processes.