2-Amino-5-chloropyrazine
[CAS# 33332-29-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 2-Amino-5-chloropyrazine
• Synonyms: 5-chloropyrazin-2-amine
• Molecular Formula: C₄H₄ClN₃
• Molecular Weight: 129.55
• CAS Registry Number: 33332-29-5
• EC Number: 689-326-8
• SMILES: C1=C(N=CC(=N1)Cl)N

Properties

• Melting point: 122-128 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety 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.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Amino-5-chloropyrazine is a heterocyclic organic compound featuring a pyrazine ring with both amino and chloro substituents. This compound has garnered attention due to its distinctive chemical structure and potential applications in various scientific and industrial fields.

The discovery of 2-Amino-5-chloropyrazine is rooted in the broader exploration of functionalized pyrazine derivatives. Pyrazine itself is a six-membered aromatic ring with two nitrogen atoms at opposite positions, which is known for its versatile reactivity and utility in organic synthesis. The introduction of substituents like amino and chloro groups to the pyrazine ring modifies its chemical behavior, enhancing its utility in specific applications.

The synthesis of 2-Amino-5-chloropyrazine typically involves several key steps. Starting from a suitable pyrazine precursor, the chlorination and amination reactions are carried out to introduce the chlorine and amino groups at the 5 and 2 positions of the ring, respectively. The process often involves the use of chlorinating agents and amine reagents under controlled conditions to ensure selective substitution and high yield. The final product is purified through techniques such as recrystallization or column chromatography to achieve the desired purity.

One of the primary applications of 2-Amino-5-chloropyrazine is in medicinal chemistry. The compound's structure is of interest for its potential bioactivity. The amino and chloro groups can participate in various chemical interactions, making 2-Amino-5-chloropyrazine a valuable building block in the synthesis of pharmaceutical compounds. For instance, it can be used to design and synthesize new drugs with potential therapeutic effects. The compound’s ability to interact with biological targets may lead to the development of novel treatments for diseases or conditions where pyrazine-based drugs are beneficial.

In addition to its role in medicinal chemistry, 2-Amino-5-chloropyrazine is utilized in agrochemical research. The compound's ability to act as a precursor for various agrochemicals is of particular interest. It can be used to develop herbicides, fungicides, and insecticides by incorporating it into more complex chemical structures. The reactivity of the amino and chloro groups allows for the modification of the pyrazine ring to create compounds with specific pesticidal properties.

Another significant application of 2-Amino-5-chloropyrazine is in materials science. The compound's unique chemical structure can influence its interaction with other materials, making it useful in the development of new materials with specific electronic or optical properties. For example, it can be employed in the synthesis of functionalized polymers or organic electronic materials, where its presence can modify the properties of the material for various applications.

Despite its utility, there are challenges associated with the use of 2-Amino-5-chloropyrazine. These include optimizing the synthesis to improve yield and purity, as well as exploring its full range of applications. Continued research is likely to focus on enhancing the efficiency of its synthesis and expanding its applications in different fields.

Future investigations into 2-Amino-5-chloropyrazine may explore its potential in new areas such as advanced materials or novel therapeutic agents. Its unique chemical properties offer opportunities for innovation in both research and industrial applications, contributing to advancements in these areas.

References

2019. The complete synthesis of favipiravir from 2-aminopyrazine. Chemical Papers, 73(6).
DOI: 10.1007/s11696-018-0654-9

2020. Methods of Synthesis of Remdesivir, Favipiravir, Hydroxychloroquine, and Chloroquine: Four Small Molecules Repurposed for Clinical Trials during the Covid-19 Pandemic. Synthesis, 52(24).
DOI: 10.1055/s-0040-1707386