2-Chloro-5-cyanopyrazine
[CAS# 36070-75-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 2-Chloro-5-cyanopyrazine
• Synonyms: 5-Chloropyrazine-2-carbonitrile
• Molecular Formula: C₅H₂ClN₃
• Molecular Weight: 139.54
• CAS Registry Number: 36070-75-4
• EC Number: 640-607-3
• SMILES: C1=C(N=CC(=N1)Cl)C#N

Properties

• Density: 1.43
• Melting point: 44-45 ºC
• Boiling point: 242 ºC
• Flash point: 100 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302+H312+H332-H302-H312-H315-H319-H332-H335
• Precautionary 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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	3	H301

Discovory and Applicatios

2-Chloro-5-cyanopyrazine is an important compound in the field of heterocyclic chemistry. The compound is characterized by the substitution of the pyrazine ring with a chlorine atom at the 2-position and a cyano group at the 5-position. The discovery of 2-chloro-5-cyanopyrazine is part of a broad study to synthesize and explore the properties of chlorinated pyrazine derivatives, which are used in pharmaceuticals and agrochemicals. The unique substitution pattern on the pyrazine ring gives it remarkable chemical versatility and reactivity.

The synthesis of 2-chloro-5-cyanopyrazine usually involves a multi-step process starting from a pyrazine derivative. A common approach begins with the nitration of pyrazine followed by reduction to obtain an aminopyrazine. The amino group is then converted to a cyano group by diazotization and Sandmeyer reaction. The last step is the chlorination of the pyrazine ring, using reagents such as phosphorus pentachloride (PCl5) or thionyl chloride (SOCl2) to introduce a chlorine atom at the 2-position.

2-Chloro-5-cyanopyrazine has a wide range of applications, especially in the pharmaceutical and agrochemical industries, due to its unique chemical structure and reactivity.

In medicinal chemistry, 2-chloro-5-cyanopyrazine is a valuable intermediate for the synthesis of a variety of bioactive molecules. The pyrazine core is integral to the development of drugs with antimicrobial, anticancer, and anti-inflammatory properties. The chlorine and cyano functional groups enhance its reactivity, allowing for further chemical modifications to optimize pharmacological properties and therapeutic effects.

This compound also plays an important role in the production of agrochemicals, including herbicides, insecticides, and fungicides. Its ability to interfere with the biological processes of pests and pathogens makes it an active ingredient in formulations to 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 its direct applications, 2-chloro-5-cyanopyrazine 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 a key compound for exploring new chemical reactions and creating innovative compounds.

Research on 2-chloro-5-cyanopyrazine continues to expand its range of applications. Future research focuses on optimizing its synthesis, exploring new derivatives, and enhancing its efficacy in various applications. The development of novel compounds based on this structure will lead to significant advances in drug discovery, agrochemical development, and materials science.