22819-07-4

Basic information

• Product Name: 3-AMINO-5-BENZYL-4H-1,2,4-TRIAZOLE
• Synonyms: (5-BENZYL-4H-1,2,4-TRIAZOLE-3-YL)AMINE;3-AMINO-5-BENZYL-4H-1,2,4-TRIAZOLE;5-Benzyl-1,2,4-triazol-3-amine;3-benzyl-1H-1,2,4-triazol-5-amine(SALTDATA: FREE);5-Benzyl-4H-1,2,4-triazol-3-amine;3-Amino-5-benzyl-1H-1,2,4-triazole;4-triazol-3-aMine;5-benzyl-4H-1
• CAS NO: 22819-07-4
• Molecular Formula: C₉H₁₀N₄
• Molecular Weight: 174.2
• Mol File: 22819-07-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 171 °C
• Boiling Point: 435.2°C at 760 mmHg
• Flash Point: 247°C
• Appearance: /
• Density: 1.281g/cm³
• Vapor Pressure: 8.93E-08mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: 2-8°C(protect from light)
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.62±0.40(Predicted)
• CAS DataBase Reference: 3-AMINO-5-BENZYL-4H-1,2,4-TRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-5-BENZYL-4H-1,2,4-TRIAZOLE(22819-07-4)
• EPA Substance Registry System: 3-AMINO-5-BENZYL-4H-1,2,4-TRIAZOLE(22819-07-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 22819-07-4(Hazardous Substances Data)

Usage

Uses

5-Benzyl-4H-1,2,4-triazol-3-amine can be used as positive modulators of GABAA1 receptor with potent anticonvulsant activity and low toxicity.

InChI:InChI=1/C9H10N4/c10-9-11-8(12-13-9)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,10,11,12,13)

Upstream product

• 14527-26-5 2-methylisothiourea sulphate 
• 937-39-3 2-phenylacetylhydrazine 
• 1937-19-5 1-aminoguanidine hydrochloride 
• 101-41-7 benzeneacetic acid methyl ester 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 591246-80-9 C₉H₁₂N₄O 
• 35604-35-4 5-benzyl[1.2.4]oxadiazol-3-ylamine 
• 1257878-63-9 3-chloro-5-benzyl-1,2,4-oxadiazole 

Downstream Products

• 1029521-10-5 2-benzyl-5-chloromethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 
• 1029520-80-6 2-benzyl-5-(((2,3-difluorophenyl)thio)methyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 
• 1431968-95-4 C₁₃H₁₅N₅O₃ 
• 1527497-97-7 N-(5-benzyl-1H-1,2,4-triazol-3-yl)-[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazin-6-amine 
• 1607425-78-4 2-benzyl-5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one 
• 1607425-77-3 2-benzyl-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one 
• 1607425-60-4 5-(benzo[d][1,3]dioxol-5-yl)-2-benzyl-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one 
• 1029521-04-7 2-benzyl-5-(4-chloro-2,5-dimethyl-phenylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 
• 1029521-09-2 2-benzyl-5-(2,5-dimethyl-furan-3-ylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 
• 1029520-93-1 2-benzyl-5-phenylsulfanylmethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 
• 1029520-94-2 2-benzyl-5-(3,4-difluorophenylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 
• 1029520-96-4 2-benzyl-5-(2,3-dichlorophenylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 
• 1029521-02-5 2-benzyl-5-(2,4-dichloro-phenylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 
• 1029521-03-6 2-benzyl-5-(3-trifluoromethoxy-phenylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 

Relevant articles and documents

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.

A Direct approach to a 6-hetarylamino[1,2,4]triazolo[4,3-b][1,2,4,5] tetrazine library

The synthesis of 6-hetarylamino[1,2,4]triazolo[4,3-b]-[1,2,4,5]tetrazines is reported. The functionalized secondary amines were constructed via a K 2CO3-mediated SNAr reaction of weakly basic hetarylamines with 3-(3,5-dimethylpyrazol-1-yl)[1,2,4]triazolo[4,3-b]-[1,2,4,5]tetrazines, which allowed displacement 3,5-dimethylpyrazolyl leaving group. Significantly, the reaction exhibited a broad substrate scope and proceeded in good yields.

Synthesis of amino-1,2,4-triazoles by reductive ANRORC rearrangements of 1,2,4-oxadiazoles

The reaction of various 1,2,4-oxadiazoles with an excess of hydrazine in DMF has been investigated. 3-Amino-1,2,4-triazoles are produced through a reductive ANRORC pathway consisting of the addition of hydrazine to the 1,2,4-oxadiazole followed by ring-opening, ring-closure, and final reduction of the 3-hydroxylamino-1,2,4-triazole intermediate. The general applicability of 1,2,4-oxadiazoles ANRORC reactivity is demonstrated also in the absence of C(5)-linked electron-withdrawing groups.