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1,2,4-Triazolo[4,3-a]pyridine, 3-(4-nitrophenyl)- is a complex organic compound with the molecular formula C9H5N5O2. It features a triazolo[4,3-a]pyridine core, which is a fused-ring system consisting of a triazole and a pyridine. The compound is further characterized by the presence of a 4-nitrophenyl group attached to the 3-position of the triazolo[4,3-a]pyridine ring. This nitro group introduces a strong electron-withdrawing effect, which can significantly influence the compound's reactivity and physical properties. The compound may be of interest in medicinal chemistry and materials science due to its unique structure and potential applications in the development of new drugs or as a building block for more complex molecules.

2746-39-6

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2746-39-6 Usage

Chemical Family

Belongs to the triazolo pyridine family.

Pharmaceutical Applications

Known for its potential pharmaceutical applications, particularly in the field of medicinal chemistry.

Chemical Structure

Consists of a pyridine ring fused to a triazolopyridine ring, with a 4-nitrophenyl group attached at the 3-position.

Biological Activities

Has been studied for its biological activities and potential as a drug candidate.

Anticancer and Antitumor Potential

Research has focused on its potential as an anticancer and antitumor agent.

Coordination Chemistry

The compound has shown potential as a ligand for use in coordination chemistry.

Material Development

It has potential applications in the development of new materials.

Check Digit Verification of cas no

The CAS Registry Mumber 2746-39-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,4 and 6 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 2746-39:
(6*2)+(5*7)+(4*4)+(3*6)+(2*3)+(1*9)=96
96 % 10 = 6
So 2746-39-6 is a valid CAS Registry Number.

2746-39-6Downstream Products

2746-39-6Relevant academic research and scientific papers

RuCl3/Oxone: An efficient combination for the synthesis of 3-aryl-[1,2,4]triazolo[4,3-a]pyridines from 2-(2-arylidenehydrazinol)pyridines

Swamy, Tallapally,Raviteja, Padma,Srikanth, Goskula,Reddy, Basi V. Subba,Ravinder, Vadde

, p. 5596 - 5598 (2016)

An efficient and convenient method for the synthesis of 3-aryl[1,2,4]triazolo[4,3-a]pyridines has been developed involving RuCl3/Oxone oxidative cyclization of 2-(2-arylidenehydrazinyl)pyridines, which occurs chemoselectively at the pyridine ni

One-pot synthesis of N-fused 1,2,4-triazoles and related heterocycles via I2/TBHP-mediated oxidative C–N bond formation

Wu, Yachuang,Yang, Yifeng,Qi, Yinliang,Du, Shimei,Zhang, Yongsheng,Ding, Liang,Zhao, Yanfang

supporting information, p. 4216 - 4220 (2018/10/26)

A metal-free iodine/TBHP-mediated oxidative C–N bond formation for the one-pot synthesis of N-fused 1,2,4-triazoles and related heterocycles via cyclization has been developed. This reaction which is amenable to scale-up affords the corresponding products with good to excellent yields and tolerates a wide range of functional groups.

Synthesis of 1,2,4-Triazolo[4,3-a]pyridines and Related Heterocycles by Sequential Condensation and Iodine-Mediated Oxidative Cyclization

Li, Ertong,Hu, Zhiyuan,Song, Lina,Yu, Wenquan,Chang, Junbiao

, p. 11022 - 11027 (2016/07/27)

A facile and efficient approach to access 1,2,4-triazolo[4,3-a]pyridines and related heterocycles has been accomplished through condensation of readily available aryl hydrazines with corresponding aldehydes followed by iodine-mediated oxidative cyclizatio

Efficient synthesis of 3-substituted 1,2,4-triazolo[4,3-a]pyridine by [bis(trifluroacetoxy)iodo]benzene-catalyzed oxidative intramolecular cyclization of heterocyclic hydrazones

Padalkar, Vikas S.,Patil, Vikas S.,Phatangare, Kiran R.,Umape, Prashant G.,Sekar

experimental part, p. 925 - 938 (2011/04/22)

A series of 1,2,4-triazolopyridines have been prepared by oxidative intramolecular cyclization of heterocyclic hydrazones with [bis(trifluroacetoxy) iodo]benzene. General applicability of this simple transformation was confirmed by synthesis of 1,2,4-triazolo[4,3-a]pyridine. The advantages of this protocol are the nontoxicity of catalyst and shorter reaction time to obtain good preparative yield.

Palladium-catalyzed coupling of aldehyde-derived hydrazones: Practical synthesis of triazolopyridines and related heterocycles

Thiel, Oliver R.,Achmatowicz, Michal M.,Reichelt, Andreas,Larsen, Robert D.

supporting information; experimental part, p. 8395 - 8398 (2010/12/25)

The palladium-catalyzed intermolecular coupling of aldehyde-derived hydrazones with chloroazines, followed by oxidative cyclization under mild conditions afforded access to a broad variety of bicyclic heterocyclic scaffolds (see scheme) that have potentia

A convenient new synthesis of fused 1,2,4-triazoles: The oxidation of heterocyclic hydrazones using copper dichloride

Ciesielski, Michael,Pufky, Daniela,D?ring, Manfred

, p. 5942 - 5947 (2007/10/03)

A series of 1,2,4-triazoles have been prepared by oxidative intramolecular cyclization of heterocyclic hydrazones with copper dichloride. General applicability of this simple transformation was confirmed by the synthesis of moderate to high yields of 1,2,

Electrochemical Synthesis of Heterocyclic Compounds. XV. Anodic Synthesis of s-Triazolopyridine Derivatives

Crljenak, Senka,Tabakovic, Ibro,Jeremic, Dragoslav,Gaon, Igor

, p. 527 - 536 (2007/10/02)

Anodic oxidation of several heterocyclic hydrazones (1a - 9a) prepared from 2-hydrazinopyridine of 2-hydrazino-4-nitropyridine and the corresponding aromatic aldehyde was performed in a CH3CN-Et4NClO4 solution with the addition of 60percent HClO4 on a platinum electrode, using controlled potentials.As a result of two-electron oxidative cyclizations, several s-triazolopyridine derivatives (1b - 9b) were prepared in yields ranging from 55 to 92percent.A mechanism rationalizing the formation of the 3-phenyl-s-triazolopyridine, 1b, has been studied by LSV, CPSV, RDE, coulometry and preparative scale electrolysis.

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