6-Chloropyrazine-2-carboxylic acid
[CAS# 23688-89-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 6-Chloropyrazine-2-carboxylic acid
• Molecular Formula: C₅H₃ClN₂O₂
• Molecular Weight: 158.54
• CAS Registry Number: 23688-89-3
• EC Number: 690-830-5
• SMILES: C1=C(N=C(C=N1)Cl)C(=O)O

Properties

• Melting point: 157 °C (decomp.)

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
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

6-Chloropyrazine-2-carboxylic acid is a well-known heterocyclic compound in organic chemistry, recognized for its applications in pharmaceuticals and agrochemicals. The molecule consists of a pyrazine ring with a chlorine atom at the 6-position and a carboxylic acid group at the 2-position. The compound was initially synthesized to explore the chemical properties and potential applications of chlorinated pyrazine derivatives.

The synthesis of 6-chloropyrazine-2-carboxylic acid involves chlorination and carboxylation reactions. The common synthetic route starts with pyrazine, which undergoes selective chlorination to introduce a chlorine atom at the 6-position. This intermediate is then carboxylated to form a carboxylic acid group at the 2-position. Another approach starts with 2,6-dichloropyrazine, where the chlorine at the 2-position is selectively converted to a carboxylic acid group by hydrolysis.

6-Chloropyrazine-2-carboxylic acid has a wide range of applications, especially in pharmaceuticals and agrochemicals, due to its unique structure and reactivity.

In medicinal chemistry, 6-chloropyrazine-2-carboxylic acid is a valuable intermediate for the synthesis of various bioactive molecules. Its pyrazine core is essential for the development of drugs with antibacterial, anticancer, and anti-inflammatory properties. The chlorine and carboxylic acid functional groups enhance its reactivity, allowing for further modification to optimize pharmacological properties.

The compound is used in the production of agrochemicals, including herbicides, insecticides, and fungicides. Its ability to disrupt the biological processes of pests and pathogens makes it an effective ingredient in formulations to protect crops and increase agricultural yields. The chlorinated pyrazine structure is particularly useful for developing compounds with increased potency and environmental stability.

In addition to its direct applications, 6-chloropyrazine-2-carboxylic acid is used in chemical research as a building block for the synthesis of more complex molecules. It is frequently used to study reaction mechanisms and develop new synthetic methods.

Ongoing research on 6-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 may 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*, 73.
DOI: 10.1016/j.bmc.2022.117046

2020. The molecular basis of pyrazinamide activity on Mycobacterium tuberculosis PanD. *Nature Communications*, 11(1).
DOI: 10.1038/s41467-019-14238-3

2017. Synthesis and biological evaluation of new 2-(6-alkyl-pyrazin-2-yl)-1H-benz[d]imidazoles as potent anti-inflammatory and antioxidant agents. *Medicinal Chemistry Research*, 26(8).
DOI: 10.1007/s00044-017-1897-7