2-(Trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrazine
[CAS# 681249-56-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 2-(Trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrazine
• Molecular Formula: C₆H₃F₃N₄
• Molecular Weight: 188.11
• CAS Registry Number: 681249-56-9
• SMILES: C1=CN2C(=NC(=N2)C(F)(F)F)C=N1

Properties

• Solubility: Very slightly soluble (0.55 g/L) (25 °C), Calc.^*
• Density: 1.69±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

2-(Trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrazine is a heterocyclic compound characterized by the substitution of the triazolo[1,5-a]pyrazine core with trifluoromethyl groups. The compound was discovered in the early 21st century due to the need to explore new chemical scaffolds in medicinal chemistry and agrochemical research. The trifluoromethyl group imparts unique electronic properties, making the compound a valuable building block for the development of new drugs and agrochemicals.

The most important application of 2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrazine is in drug development. It serves as a core structure for drug design due to its stability and ability to modulate biological activity. This compound has been used to synthesize kinase inhibitors and other enzyme inhibitors, providing potential treatments for cancer, inflammatory diseases, and neurological diseases.

In agrochemical research, 2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrazine is used to make herbicides, fungicides, and insecticides. Its structure contributes to improved efficacy and selectivity, resulting in effective pest control while minimizing environmental impact. The trifluoromethyl group enhances the metabolic stability of agrochemicals, prolonging their activity in the field.

The trifluoromethyl group of this compound is a valuable functional moiety in synthetic organic chemistry. It is used to design new catalysts and ligands, as well as in cross-coupling reactions and other transformations to introduce the trifluoromethyl group into composite molecules.

In materials science, 2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrazine has been intensively studied for its potential in developing advanced materials with unique electronic properties. Its incorporation into polymers and other materials can enhance conductivity and thermal stability, among other things, helping to create innovative materials for the electronics industry and other applications.

In addition to its direct application in drugs, 2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrazine can be used as a molecular probe in medicinal chemistry. Its structural properties make it useful for studying drug-receptor interactions and optimizing lead compounds in drug design.

References

none