Methyl 5-chloropyrazine-2-carboxylate
[CAS# 33332-25-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: Methyl 5-chloropyrazine-2-carboxylate
• Molecular Formula: C₆H₅ClN₂O₂
• Molecular Weight: 172.57
• CAS Registry Number: 33332-25-1
• EC Number: 627-670-2
• SMILES: COC(=O)C1=CN=C(C=N1)Cl

Properties

• Solubility: 2.373e+004 mg/L (25 °C water)
• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.534, Calc.^*
• Melting point: 56.32 °C
• Boiling Point: 242.8±35.0 °C (760 mmHg), Calc.^*, 244.20 °C
• Flash Point: 100.6±25.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

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

Hazard Classification

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

Discovery and Applications

5-Chloropyrazine-2-carboxylic acid methyl ester is a noteworthy compound in the field of organic chemistry. It is characterized by a chlorine atom at the 5-position and a methyl ester group at the 2-position of the pyrazine ring. The compound was first synthesized in the study of developing novel pyrazine derivatives with potential biological and industrial applications. The introduction of chlorine atoms and methyl ester groups into the pyrazine ring creates a versatile building block for a variety of chemical reactions and applications.

The synthesis of 5-chloropyrazine-2-carboxylic acid methyl ester involves the chlorination and esterification of pyrazine carboxylic acid derivatives. A common synthetic route starts with pyrazine-2-carboxylic acid, which is chlorinated at the 5-position using reagents such as phosphorus pentachloride (PCl5) or thionyl chloride (SOCl2). The resulting 5-chloropyrazine-2-carboxylic acid is then esterified using methanol and an acid catalyst to give 5-chloropyrazine-2-carboxylic acid methyl ester.

5-Chloropyrazine-2-carboxylic acid methyl ester has a wide range of applications due to its unique chemical structure and reactivity, especially in the pharmaceutical and agrochemical industries.

In medicinal chemistry, methyl 5-chloropyrazine-2-carboxylate is an important intermediate in the synthesis of various biologically active compounds. 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 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 addition to its direct applications, methyl 5-chloropyrazine-2-carboxylate 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. Its reactivity and versatility make it a valuable compound for exploring new chemical reactions and creating innovative compounds.

Ongoing research on methyl 5-chloropyrazine-2-carboxylate 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 novel compounds based on this structure may lead to breakthroughs in drug discovery, agrochemical development, and materials science.

References

1995. Pyrazinoic Acid Esters with Broad Spectrum in Vitro Antimycobacterial Activity. Journal of Medicinal Chemistry, 38(20).
DOI: 10.1021/jm00020a003

1996. Quantitative Structure-Activity Relationships for the in Vitro Antimycobacterial Activity of Pyrazinoic Acid Esters. Journal of Medicinal Chemistry, 39(1).
DOI: 10.1021/jm950538t

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(6).
DOI: 10.1007/s00044-015-1352-6