2-Chloro-3-(trifluoromethyl)pyrazine
[CAS# 191340-90-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 2-Chloro-3-(trifluoromethyl)pyrazine
• Molecular Formula: C₅H₂ClF₃N₂
• Molecular Weight: 182.53
• CAS Registry Number: 191340-90-6
• EC Number: 873-573-5
• SMILES: C1=CN=C(C(=N1)C(F)(F)F)Cl

Properties

• Solubility: Sparingly soluble (17 g/L) (25 °C), Calc.^*
• Density: 1.504±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 163.4±35.0 °C (760 Torr), Calc.^*
• Flash point: 52.6±25.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H226-H302-H315-H318-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2-Chloro-3-(trifluoromethyl)pyrazine is a well-known compound in the field of heterocyclic chemistry, characterized by the substitution of the pyrazine ring with a chlorine atom at the 2-position and a trifluoromethyl group at the 3-position. The first synthesis of this compound is part of a broad effort to explore the chemical properties and potential applications of halogenated pyrazines, especially those with electron-withdrawing groups such as the trifluoromethyl group.

The synthesis of 2-chloro-3-(trifluoromethyl)pyrazine involves a multistep process starting from readily available precursors. The typical synthetic route involves the formation of the pyrazine ring followed by selective chlorination and the introduction of the trifluoromethyl group. A common approach is to react 2,3-dichloropyrazine with a trifluoromethylating agent such as trifluoromethyl iodide or trifluoromethyltrimethylsilane under specific conditions to achieve the desired substitution pattern.

2-Chloro-3-(trifluoromethyl)pyrazine has a wide range of applications due to its unique chemical structure and reactivity, especially in the fields of medicinal chemistry, agrochemicals, and materials science.

In medicinal chemistry, 2-chloro-3-(trifluoromethyl)pyrazine is a key intermediate in the synthesis of various bioactive molecules. The presence of chlorine and trifluoromethyl groups enhances the compound's pharmacokinetic properties, such as metabolic stability and bioavailability. It is particularly useful in the design of enzyme inhibitors and receptor modulators, with potential applications in the treatment of cancer, inflammation, and infectious diseases.

This compound is also valuable in the development of agrochemicals, including herbicides, fungicides, and insecticides. The trifluoromethyl group imparts high lipophilicity and metabolic resistance, making 2-chloro-3-(trifluoromethyl)pyrazine derivatives effective against a wide range of pests and pathogens. These properties help protect crops and improve agricultural productivity.

In materials science, 2-chloro-3-(trifluoromethyl)pyrazine is used to synthesize novel polymers and advanced materials. Its unique electronic properties make it suitable for organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaics. Incorporation of this compound into polymer structures can enhance its thermal stability and electronic properties.

Ongoing research on 2-chloro-3-(trifluoromethyl)pyrazine is expected to further explore its potential applications. Future research may focus on optimizing its synthesis, improving its reactivity, and exploring new therapeutic areas. In addition, the development of novel derivatives and analogs can expand its usefulness in various scientific disciplines such as drug discovery and advanced materials.

References

none