2-Amino-3,5-dibromopyrazine
[CAS# 24241-18-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 2-Amino-3,5-dibromopyrazine
• Synonyms: 3,5-Dibromopyrazin-2-ylamine
• Molecular Formula: C₄H₃Br₂N₃
• Molecular Weight: 252.89
• CAS Registry Number: 24241-18-7
• EC Number: 628-514-6
• SMILES: C1=C(N=C(C(=N1)N)Br)Br

Properties

• Melting point: 114-117 °C

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H301-H315-H318-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P305+P354+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
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	3	H331
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	3	H311

• Transport Information: UN 2811

Discovery and Applications

2-Amino-3,5-dibromopyrazine is a halogenated heterocyclic compound characterized by a pyrazine ring substituted with amino and bromine groups at specific positions. The presence of two bromine atoms at the 3rd and 5th positions, along with an amino group at the 2nd position, imparts unique reactivity and stability to the molecule. This makes it an important building block in various chemical syntheses and applications.

The discovery of 2-amino-3,5-dibromopyrazine is closely associated with the exploration of pyrazine derivatives, which have been of significant interest due to their diverse chemical and biological properties. Pyrazines, as a class, are known for their aromaticity and nitrogen content, which contribute to their utility in a wide range of chemical reactions. The introduction of bromine atoms into the pyrazine ring enhances the reactivity of the compound, particularly in cross-coupling reactions that are widely used in organic synthesis.

One of the primary applications of 2-amino-3,5-dibromopyrazine is as an intermediate in the synthesis of more complex organic molecules. The compound's bromine atoms serve as functional sites for further chemical modifications, making it an ideal precursor in the construction of various heterocyclic compounds. These heterocycles are often of interest in pharmaceutical chemistry, where they serve as core structures in the development of drugs and bioactive molecules. The amino group provides additional versatility, allowing for the introduction of various substituents that can modulate the biological activity of the resulting compounds.

In pharmaceutical research, 2-amino-3,5-dibromopyrazine has been investigated for its potential to serve as a key intermediate in the synthesis of kinase inhibitors, which are important in the treatment of cancer and other diseases. The specific positioning of the bromine atoms facilitates selective reactions that lead to the formation of complex molecules with desired pharmacological properties. Additionally, the compound's reactivity makes it a valuable starting material in the design of new chemical entities with potential therapeutic applications.

Beyond its role in pharmaceuticals, 2-amino-3,5-dibromopyrazine is also used in the development of advanced materials. The compound can be incorporated into polymers and other materials that require specific electronic or structural properties. For example, it can be used to create materials with enhanced conductivity or stability, which are essential in the production of electronic components. The brominated pyrazine ring system offers a combination of rigidity and reactivity, making it suitable for inclusion in materials that need to maintain performance under demanding conditions.

Environmental and toxicological studies also consider compounds like 2-amino-3,5-dibromopyrazine due to their potential persistence and bioactivity. The presence of halogen atoms, particularly bromine, raises concerns about the environmental impact and safety of these compounds. As a result, research into the degradation pathways and environmental fate of halogenated pyrazines is ongoing, aiming to mitigate any potential negative effects.

The ongoing research into 2-amino-3,5-dibromopyrazine continues to explore its potential in various fields. Advances in synthetic chemistry have allowed for more efficient and selective methods of producing this compound, which in turn has expanded its applications. Whether as a precursor in drug development or as a component in advanced materials, 2-amino-3,5-dibromopyrazine remains a compound of significant interest in both academic and industrial chemistry.

References

2022. Synthetic Coelenterazine Derivatives and Their Application for Bioluminescence Imaging. *Methods in Molecular Biology*, 2524.
DOI: 10.1007/978-1-0716-2453-1_2

2019. The complete synthesis of favipiravir from 2-aminopyrazine. *Chemical Papers*, 73(7).
DOI: 10.1007/s11696-018-0654-9

2014. Strategies for Large-Scale Synthesis of Coelenterazine for in Vivo Applications. *Synthesis*, 46(3).
DOI: 10.1055/s-0033-1340556