3-Chloropyrazine-2-carboxylic acid
[CAS# 27398-39-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 3-Chloropyrazine-2-carboxylic acid
• Molecular Formula: C₅H₃ClN₂O₂
• Molecular Weight: 158.54
• CAS Registry Number: 27398-39-6
• EC Number: 676-250-5
• SMILES: C1=CN=C(C(=N1)C(=O)O)Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

3-Chloropyrazine-2-carboxylic acid is a noteworthy compound in heterocyclic chemistry, characterized by a chlorine atom at the 3-position and a carboxylic acid group at the 2-position of the pyrazine ring. This compound was initially synthesized in a study exploring the chemical properties and potential applications of chlorinated pyrazine derivatives. The introduction of a chlorine atom and a carboxylic acid group on the pyrazine ring creates a versatile building block for a variety of chemical reactions and applications.

The synthesis of 3-chloropyrazine-2-carboxylic acid involves multiple steps, starting from a pyrazine derivative. A common synthetic route involves the chlorination of pyrazine-2-carboxylic acid, using reagents such as phosphorus pentachloride (PCl5) or thionyl chloride (SOCl2) to introduce a chlorine atom at the 3-position. This selective chlorination is followed by a purification step to isolate the desired product, ensuring high yield and purity.

3-Chloropyrazine-2-carboxylic acid has a wide range of applications, especially in the fields of pharmaceuticals, agrochemicals, and materials science, due to its unique chemical structure and reactivity.

In medicinal chemistry, 3-chloropyrazine-2-carboxylic acid is a key intermediate in the synthesis of various bioactive molecules. Its pyrazine core structure is essential for the development of drugs with antimicrobial, anticancer, and anti-inflammatory properties. The chlorine and carboxylic acid functional groups enhance its reactivity, allowing for further modifications to optimize pharmacological properties and improve drug efficacy.

This compound is also valuable in the production of agrochemicals, including herbicides, insecticides, and fungicides. Its ability to interfere with the biological processes of pests and pathogens makes it an effective ingredient in formulations to protect crops and increase agricultural productivity. The chlorinated pyrazine structure is particularly useful for the development of compounds with enhanced potency and environmental stability.

In addition to its direct applications, 3-chloropyrazine-2-carboxylic acid is frequently used in chemical research as a building block for the synthesis of more complex molecules. It is used to study reaction mechanisms and develop new synthetic methods. Its reactivity and versatility make it an important compound for exploring new chemical reactions and creating innovative compounds.

Ongoing research on 3-chloropyrazine-2-carboxylic acid is expected to further expand its range of applications. Future research may focus on optimizing its synthesis, exploring new derivatives, and improving its efficacy in various applications. The development of novel compounds based on this structure could lead to breakthroughs in drug discovery, agrochemical development, and materials science.

References

2022. Structure activity relationship of pyrazinoic acid analogs as potential antimycobacterial agents. Bioorganic & Medicinal Chemistry, 74.
DOI: 10.1016/j.bmc.2022.117046

2013. In-silico design, synthesis and evaluation of novel DNA-gyrase inhibitors. Medicinal Chemistry Research, 22(10).
DOI: 10.1007/s00044-013-0518-3

2007. Antimicrobial Evaluation of Some Arylsulfanylpyrazinecarboxylic acid Derivatives. Medicinal Chemistry, 3(3).
DOI: 10.2174/157340607780620635