61456-87-9

Basic information

• Product Name: 1H-1,2,3-Triazole-4-carbonitrile, 1-phenyl-
• CAS NO: 61456-87-9
• Molecular Formula: C9H6N4
• Molecular Weight: 170.173
• Mol File: 61456-87-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1H-1,2,3-Triazole-4-carbonitrile, 1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1,2,3-Triazole-4-carbonitrile, 1-phenyl-(61456-87-9)
• EPA Substance Registry System: 1H-1,2,3-Triazole-4-carbonitrile, 1-phenyl-(61456-87-9)

Safety Data

• Hazardous Substances Data: 61456-87-9(Hazardous Substances Data)

Usage

Triazole Derivative

It is derived from the triazole ring, which is a five-membered ring containing three nitrogen atoms.

Carbonitrile Compound

The presence of a carbonitrile group (-CN) in the molecule.

Building Block in Organic Synthesis

It is used as a starting material for the synthesis of more complex organic compounds.

Phenyl Group

The phenyl group (C6H5) is attached to the 1-position of the triazole ring, providing unique properties to the compound.

Applications

Pharmaceutical industry, synthesis of potential drug candidates, and preparation of other functionalized triazole derivatives with potential biological activity.

Chemical and Physical Properties

The phenyl group attachment influences the compound's reactivity, stability, and other properties, making it valuable in various applications.

Intermediate

It serves as an intermediate in the synthesis of more complex molecules, particularly in the pharmaceutical and chemical industries.

Upstream product

• 20271-39-0 5-amino-1-phenyl-1H-1,2,3-triazole-4-carbonitrile 
• 107-13-1 acrylonitrile 
• 622-37-7 Phenyl azide 
• 920-37-6 2-Chloroacrylonitrile 
• 62-53-3 aniline 
• 90886-87-6 1‐(4‐nitrophenyl)‐1H‐1,2,3‐triazole‐4‐yl‐methanol 
• 133902-63-3 [1-[1-(4-Nitro-phenyl)-1H-[1,2,3]triazol-4-yl]-meth-(E)-ylidene]-phenyl-amine 
• 133902-67-7 ethyl 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate 
• 133902-62-2 [1-[1-(4-Chloro-phenyl)-1H-[1,2,3]triazol-4-yl]-meth-(E)-ylidene]-phenyl-amine 
• 133902-50-8 (4-Chloro-phenyl)-[1-(1-phenyl-1H-[1,2,3]triazol-4-yl)-meth-(E)-ylidene]-amine 
• 113934-26-2 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxaldehyde 
• 133902-54-2 (E)-1-phenyl-1H-1,2,3-triazole-4-carbaldehydeoxime 
• 103755-58-4 (1-phenyl-1H-1,2,3-triazole-4-yl)methanol 
• 34296-51-0 1-phenyl-1,2,3-triazole-4-carbaldehyde 

Downstream Products

• 134541-91-6 1-phenyl-1H-1,2,3-triazole-4-carboxylic acid chloride 
• 4600-04-8 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid 

Relevant articles and documents

Flow hydrodediazoniation of aromatic heterocycles

Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles, confirming the wide scope and substituent-tolerance of the processes. Flow equipment was utilized and the process optimised to overcome the problematically-unstable intermediates that have restricted yields in previous studies relying on batch procedures. Various common organic solvents were investigated as potential hydride sources. The approach has allowed key structures, such as amino-pyrazoles and aminopyridines, to be deaminated in good yield using a purely organic-soluble system.

Discovery of a novel 6,7-disubstituted-4-(2-fluorophenoxy)quinolines bearing 1,2,3-triazole-4-carboxamide moiety as potent c-Met kinase inhibitors

A series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives possessing 1,2,3-triazole-4-carboxamide moiety were designed, synthesized and evaluated for their in vitro cytotoxic activities against four typical cancer cell lines (A549, H460, HT-29, and MKN-45). Most compounds showed moderate-to-excellent antiproliferative activity. Compounds 32, 36, 37, 45, 51, and 52 were further examined for their inhibitory activity against c-Met kinase. The promising compound 37, with a c-Met IC50 value of 2.27 nM, was identified as a multitargeted receptor tyrosine kinase inhibitor. The analysis of their structure-activity relationships indicated that compounds with EWGs, especially chloro group, at 2-position on the phenyl ring (moiety B) have potent antitumor activity.

Molecular Rearrangements of 4-Iminomethyl-1,2,3-Triazoles. Replacement of 1-Aryl Substituents in 1H-1,2,3-Triazole-4-carbaldehydes

The two structural isomers, 4 and 5, of 1-substituted-4-iminomethyl-1,2,3-triazoles are interconvertible when heated in dimethyl sulfoxide at 80 deg C.The equilibrium position depends on the electronic properties of the R-substituent, favoring 5 for R = alkyl, benzyl and anisyl, and 4 for p-chlorophenyl and p-nitrophenyl.An interesting application is the synthesis of 1-alkyl-1,2,3-triazole-4-carbaldehydes from 1-phenyl-1,2,3-triazole-4-carbaldehyde by Scheme I.The hydrazones 4i, j and the oxime 4k do not rearrange due to an unfavorable Z-configuration around the C=N bond, whereas the acyloximino derivative 4m is converted into the nitrile 11.The structures of the products have been fully characterized by 13C nmr spectroscopy and the mechanistic details of the rearrangement are discussed.