Methyl 6-chloro-2-pyrazinecarboxylate
[CAS# 23611-75-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: Methyl 6-chloro-2-pyrazinecarboxylate
• Molecular Formula: C₆H₅ClN₂O₂
• Molecular Weight: 172.57
• CAS Registry Number: 23611-75-8
• EC Number: 807-301-3
• SMILES: COC(=O)C1=CN=CC(=N1)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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

6-Chloro-2-pyrazinecarboxylic acid methyl ester is an important compound in the field of organic chemistry, recognized for its wide applications in the pharmaceutical and agrochemical industries. It features a chlorine atom at the 6-position and a carboxylate group at the 2-position of the pyrazine ring. This compound was first synthesized in the study of developing novel pyrazine derivatives with potential biological activity.

The synthesis of 6-chloro-2-pyrazinecarboxylic acid methyl ester involves the chlorination and esterification of pyrazinecarboxylic acid derivatives. A common synthetic route starts with pyrazine-2-carboxylic acid, which is then chlorinated at the 6-position using reagents such as phosphorus pentachloride (PCl5) or thionyl chloride (SOCl2). The resulting 6-chloropyrazine-2-carboxylic acid is subsequently esterified using methanol and an acid catalyst to give 6-chloro-2-pyrazinecarboxylic acid methyl ester.

6-Chloro-2-pyrazinecarboxylic acid methyl ester has a wide range of applications due to its unique chemical properties and reactivity, especially in the fields of pharmaceuticals, agrochemicals, and materials science.

In medicinal chemistry, methyl 6-chloro-2-pyrazinecarboxylate is a valuable intermediate for the synthesis of various biologically active compounds. Its pyrazine core structure is essential for the development of drugs with antimicrobial, anticancer, and anti-inflammatory properties. The chlorine and ester functional groups enhance its reactivity, allowing for further modification and optimization of pharmacological properties.

The compound is also 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 the development of compounds with increased potency and environmental stability.

In materials science, methyl 6-chloro-2-pyrazinecarboxylate is used to synthesize advanced materials with specific electronic and optical properties. It can be incorporated into polymers and other materials to enhance their thermal stability and electronic properties. These materials can be used in organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaics.

Ongoing research on methyl 6-chloro-2-pyrazinecarboxylate is expected to further expand its range of applications. Future research will 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

2015. Novel lead generation of an anti-tuberculosis agent active against non-replicating mycobacteria: exploring hybridization of pyrazinamide with multiple fragments. Medicinal Chemistry Research, 24(3).
DOI: 10.1007/s00044-015-1352-6