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

Description

5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE is an organic compound with the molecular formula C9H9N5. It is a derivative of 1,2,4-triazole, featuring a phenyl group attached to the 5th position of the triazole ring. 5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE is known for its potential applications in various fields, particularly in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE is used as an intermediate in the synthesis of WP155, a compound with potential therapeutic applications. Its role in the synthesis process is crucial for the development of new drugs and pharmaceutical products.
Used in Biological Studies:
5-PHENYL-1H-1,2,4-TRIAZOL-3-AMINE is also utilized in biological research to assess its pharmacological activity. It is particularly relevant in methods aimed at reducing susceptibility to tumor formation induced by 3-deoxyglucosone and its precursors. This application highlights the compound's potential in cancer research and the development of novel cancer prevention strategies.

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 
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• 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

• 36372-09-5 5-methyl-2-phenyl-4H-[1,2,4]triazolo[1,5-a]pyrimidin-7-one 
• 107518-46-7 5,7-dimethyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine 
• 74258-83-6 3-{1-[(Z)-5-Phenyl-2H-[1,2,4]triazol-3-ylimino]-ethyl}-dihydro-furan-2-one 
• 104690-50-8 6-Bromo-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 
• 104690-35-9 6-Iodo-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 
• 80670-36-6 3-diazo-5-phenyl-3H-1,2,4-triazole 
• 28151-85-1 5-phenyl-1,2,4-triazole-3-diazonium tetrafluoroborate 
• 99777-32-9 C₁₀H₆N₇O₂^(1-)*Na⁽¹⁺⁾ 
• 83809-89-6 2-phenyl-6-nitro-7-oxo-4,7-dihydro-1,2,4-triazolo<5,1-c><1,2,4>triazine 
• 87253-63-2 5,7-di-n-propyl-2-phenyl-s-triazolo<1,5-a>pyrimidine 
• 28610-03-9 5-amino-2-phenyl-<1,2,4>triazolo<1,5-a><1,3,5>triazine 
• 107753-08-2 2-Phenyl-6-nitro-7-hydroxy-4,7-dihydro-1,2,4-triazolo<5,1-c><1,2,4>triazine 
• 105411-96-9 2-Phenyl-6-nitro-1,2,4-triazolo<1,5-a>pyrimidine 
• 168893-24-1 5-Amino-1-[methylamino(thiocarbonyl)]-3-phenyl-1H-1,2,4-triazole 

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.

Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors

Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.

Discovery of [1,2,4]-triazolo [1,5-a]pyrimidine-7(4H)-one derivatives as positive modulators of GABAA1 receptor with potent anticonvulsant activity and low toxicity

In searching for more effective and safer antiepileptic drugs, a series of 2,5-disubstituted [1,2,4]-triazolo[1,5-a]pyrimidine-7(4H)-one derivatives were designed and synthesized. Spontaneous Ca2+ oscillations (SCOs) of cortical neurons were used for in vitro phenotypic screening. Maximal electroshock test (MES) and pentylenetetrazole (PTZ) test were used to access their anticonvulsant activity, and rotarod test was used to estimate their neurotoxicity. The active compounds in in vitro model are specifically effective in pentylenetetrazole (PTZ)-induced epilepsy model but not maximal electroshock (MES) model, more importantly with lower neurotoxicity as compared to commonly used drugs. Among them, compound 5c and 5e showed significant anticonvulsant activities in PTZ-induced epilepsy model with ED50 values at 31.81 mg/kg and 40.95 mg/kg, respectively. These compounds have improved neurotoxicity with protective index (PI = TD50/ED50) values at 17.22 and 9.09, respectively. Finally we demonstrated that compound 5c and 5e mainly acted on GABAA receptor as positive modulators but not sodium channels. Thus the present study has provided potential candidates for further investigation in epilepsy.