Methyl 6-(trifluoromethyl)pyrazine-2-carboxylate
[CAS# 1644548-81-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: Methyl 6-(trifluoromethyl)pyrazine-2-carboxylate
• Molecular Formula: C₇H₅F₃N₂O₂
• Molecular Weight: 206.12
• CAS Registry Number: 1644548-81-1
• SMILES: COC(=O)C1=CN=CC(=N1)C(F)(F)F

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.445, Calc.^*
• Boiling Point: 225.4±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 90.1±27.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

Methyl 6-(trifluoromethyl)pyrazine-2-carboxylate is a compound with wide applications in the pharmaceutical and flavoring industries. This pyrazine derivative has attracted much attention due to its unique chemical properties and versatility.

The synthesis and preliminary characterization of methyl 6-(trifluoromethyl)pyrazine-2-carboxylate were first reported by Li et al. in 2015. The researchers developed synthetic methods to introduce trifluoromethyl and ester functional groups into the pyrazine ring, highlighting its potential as a precursor for drug synthesis and other applications.

Methyl 6-(trifluoromethyl)pyrazine-2-carboxylate has a stable pyrazine core with a trifluoromethyl group at the 6-position and an ester group at the 2-position. These structural elements give it favorable physicochemical properties, such as enhanced lipophilicity and metabolic stability, which are essential for pharmaceutical applications.

The compound is a key intermediate in the synthesis of drugs targeting various therapeutic areas, including central nervous system diseases and cardiovascular diseases. The study by Chen et al. highlights its role in the development of novel drug candidates in medicinal chemistry.

Due to its aromatic properties, methyl 6-(trifluoromethyl)pyrazine-2-carboxylate is used in the flavor and fragrance industry, imparting a unique, slightly nutty aroma and is used in food and perfume formulations to enhance their sensory properties.

Ongoing research continues to explore new synthetic routes and applications for methyl 6-(trifluoromethyl)pyrazine-2-carboxylate. The focus is on optimizing its synthesis for cost-effectiveness and expanding its applications in pharmaceuticals, flavorings, and other areas.

References

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