3-Chloropyrazine-2-carbaldehyde
[CAS# 121246-96-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 3-Chloropyrazine-2-carbaldehyde
• Molecular Formula: C₅H₃ClN₂O
• Molecular Weight: 142.54
• CAS Registry Number: 121246-96-6
• EC Number: 821-114-4
• SMILES: C1=CN=C(C(=N1)C=O)Cl

Properties

• Density: 1.432
• Boiling point: 214 °C
• Flash point: 83 °C

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

Discovery and Applications

3-Chloropyrazine-2-carboxaldehyde is a heterocyclic organic compound that has attracted much attention in the fields of synthesis and medicinal chemistry. The compound belongs to the pyrazine family and is characterized by a chlorine atom at the 3-position and an aldehyde group at the 2-position of the pyrazine ring. It was synthesized in the context of exploring functionalized pyrazines for various chemical applications.

The synthesis of 3-chloropyrazine-2-carboxaldehyde involves chlorination and formylation reactions. A common approach is the chlorination of pyrazine derivatives followed by formylation to introduce the aldehyde group. Alternatively, starting from commercially available 2-chloropyrazine, formylation can be achieved using Vilsmeier-Haack conditions, where DMF and POCl3 are used to effectively introduce the aldehyde group.

3-Chloropyrazine-2-carboxaldehyde is widely used in medicinal chemistry, agrochemicals, and materials science due to the presence of its reactive aldehyde group and chlorine, which can be further functionalized.

The compound is a valuable intermediate in the synthesis of various drugs. Its reactive aldehyde group can be used to generate Schiff bases, which are important intermediates in the synthesis of drugs. Furthermore, 3-chloropyrazine-2-carboxaldehyde derivatives have the ability to interact with biological targets and can be used as antiviral, antibacterial, and anticancer agents.

In the field of agrochemicals, 3-chloropyrazine-2-carboxaldehyde is a key component in the synthesis of pesticides and herbicides. Its structural features can help develop compounds that can protect crops from pests and diseases, thereby improving agricultural productivity.

In addition to biological applications, 3-chloropyrazine-2-carboxaldehyde is also used in materials science to synthesize new polymers and organic materials. Its incorporation into polymer structures can enhance the electronic and optical properties of materials, making them suitable for organic electronics and photonics applications.

Research on 3-chloropyrazine-2-carboxaldehyde continues to expand its potential applications. Future research may focus on optimizing synthetic routes, enhancing the biological activity of its derivatives, and exploring new applications for advanced materials. Developing more efficient and sustainable synthetic methods will also be a key area of ​​focus, aiming to reduce the environmental impact of its production.

References

2017. Magnetic properties of copper(II) chloro complex with formylpyrazine-N(4)-methylthiosemicarbazone. Magnetic Properties of Paramagnetic Compounds.
DOI: 10.1007/978-3-662-54237-8_56

2017. Magnetic properties of copper(II) chloro complex with formylpyrazineN(4)-ethylthiosemicarbazone. Magnetic Properties of Paramagnetic Compounds.
DOI: 10.1007/978-3-662-54237-8_58

2017. Magnetic properties of copper(II) chloro complex with formylpyrazineN(4)-dimethylthiosemicarbazone. Magnetic Properties of Paramagnetic Compounds.
DOI: 10.1007/978-3-662-54237-8_62