Methyl 3-chloro-2-pyrazinecarboxylate
[CAS# 27825-21-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: Methyl 3-chloro-2-pyrazinecarboxylate
• Molecular Formula: C₆H₅ClN₂O₂
• Molecular Weight: 172.57
• CAS Registry Number: 27825-21-4
• EC Number: 800-672-2
• SMILES: COC(=O)C1=NC=CN=C1Cl

Properties

• Melting point: 34-35 ºC

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

3-Chloro-2-pyrazinecarboxylic acid methyl ester is an important compound in organic and medicinal chemistry characterized by the substitution of the pyrazine ring with a chlorine atom at the 3-position and a methyl ester group at the 2-position. The compound was originally synthesized as part of a research effort to explore the chemical properties and potential applications of chlorinated pyrazine derivatives. The unique combination of a chlorine atom and a methyl ester group on the pyrazine ring creates a versatile building block for a variety of chemical reactions and applications.

The synthesis of 3-chloro-2-pyrazinecarboxylic acid methyl ester involves several steps, typically starting from pyrazine-2-carboxylic acid. 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 intermediate 3-chloropyrazine-2-carboxylic acid is then esterified using methanol and an acid catalyst to form the final product, 3-chloro-2-pyrazinecarboxylic acid methyl ester.

Due to its unique chemical structure and reactivity, methyl 3-chloro-2-pyrazinecarboxylate has found a wide range of applications, particularly in pharmaceuticals, agrochemicals, and materials science.

In medicinal chemistry, methyl 3-chloro-2-pyrazinecarboxylate is a key intermediate in the synthesis of a variety of bioactive molecules. The 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 modifications to optimize pharmacological properties and improve drug efficacy.

The compound is also valuable in the production of agrochemicals, including herbicides, insecticides, and fungicides. It is able to interfere with the biological processes of pests and pathogens, becoming an active ingredient in formulations that 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 direct applications, methyl 3-chloro-2-pyrazinecarboxylate 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 methyl 3-chloro-2-pyrazinecarboxylate is expected to further expand its applications. Future research focuses on optimizing its synthesis, exploring new derivatives, and improving its efficacy in various applications. The development of new compounds based on this structure could lead to breakthroughs in drug discovery, agrochemical development, and materials science.