2-Chloro-3-nitropyrazine
[CAS# 87885-43-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 2-Chloro-3-nitropyrazine
• Synonyms: 3-Chloro-2-nitropyrazine
• Molecular Formula: C₄H₂ClN₃O₂
• Molecular Weight: 159.53
• CAS Registry Number: 87885-43-6
• SMILES: C1=CN=C(C(=N1)[N+](=O)[O-])Cl

Properties

• Density: 1.600
• Boiling point: 283 °C
• Flash point: 125 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

2-Chloro-3-nitropyrazine is a highly interesting compound that has attracted much attention due to its wide range of applications in medicine, agrochemicals, and materials science. 2-Chloro-3-nitropyrazine is synthesized by nitration of 2-chloropyrazine, a simple process that introduces a nitro group at the 3-position of the pyrazine ring. The synthesis of this compound represents a major achievement in heterocyclic chemistry, providing a route to obtain nitrogen-containing aromatic compounds with specific chemical properties.

The molecular structure of 2-chloro-3-nitropyrazine consists of a pyrazine ring with a chlorine substituent at the 2-position and a nitro group at the 3-position. This arrangement gives it specific chemical properties, including moderate solubility in organic solvents and a propensity for aromatic substitution reactions. The presence of electron-withdrawing groups affects its reactivity, making it valuable in various chemical transformations.

In pharmaceuticals, 2-chloro-3-nitropyrazine is a key intermediate in the synthesis of drug compounds. Its functional groups are able to modify the biological activity and pharmacokinetic properties of drug molecules. Researchers have explored the potential applications of its derivatives in drug discovery programs, focusing on its role in developing therapeutic agents for various medical conditions.

In agrochemicals, derivatives of 2-chloro-3-nitropyrazine are used as precursors for the synthesis of insecticides and herbicides. These compounds exhibit biological activity against specific pests and weeds, aiding in the development of effective crop protection agents. Their selective toxicity and environmental compatibility make them essential tools in modern agricultural practices.

From a chemical perspective, 2-chloro-3-nitropyrazine is a versatile building block in organic synthesis and materials science. Its reactivity allows for the introduction of different functional groups, aiding in the creation of novel compounds with tailored properties. It is used in the synthesis of dyes, polymers, and specialty chemicals in industrial applications, demonstrating its usefulness in the creation of advanced materials and chemical processes.

Research on 2-chloro-3-nitropyrazine continues to grow, aided by its unique chemical properties and wide-ranging potential for applications. Future studies aim to explore its environmental impact, develop more efficient synthetic methods, and expand its usefulness in emerging fields such as nanotechnology and biotechnology.

References

none