2-Amino-6-bromopyridine
[CAS# 19798-81-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Bromopyridine
• Name: 2-Amino-6-bromopyridine
• Synonyms: 6-Bromo-2-pyridinamine
• Molecular Formula: C₅H₅BrN₂
• Molecular Weight: 173.01
• CAS Registry Number: 19798-81-3
• EC Number: 606-385-7
• SMILES: C1=CC(=NC(=C1)Br)N

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Melting point: 88-91 °C
• Index of Refraction: 1.636, Calc.^*
• Boiling Point: 273.0±20.0 °C (760 mmHg), Calc.^*
• Flash Point: 118.9±21.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

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

Discovery and Applications

2-Amino-6-bromopyridine is a significant heterocyclic compound that belongs to the pyridine family. Its discovery can be traced back to the mid-20th century, amidst ongoing research into nitrogen-containing heterocycles, which are of considerable interest due to their diverse biological activities and applications in various fields, including pharmaceuticals and agrochemicals. The compound is synthesized through various methods, including electrophilic bromination of 2-amino-pyridine derivatives, leading to the introduction of the bromine atom at the 6-position of the pyridine ring.

The unique structure of 2-amino-6-bromopyridine, featuring both amino and bromine functional groups, endows it with valuable properties. It is primarily used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. The amino group allows for further derivatization, making it a versatile building block in medicinal chemistry. Researchers have explored its potential applications in developing antiviral, antibacterial, and antifungal agents.

In addition to its medicinal applications, 2-amino-6-bromopyridine has gained attention in materials science. It has been used in the synthesis of functionalized polymers and ligands for catalysis. The compound’s ability to form coordination complexes with transition metals also opens avenues for its use in catalysis and material design.

Overall, the discovery and application of 2-amino-6-bromopyridine highlight its significance in synthetic chemistry and its role as a versatile building block for various chemical transformations and applications. As research continues, its potential for new applications in drug discovery and materials science remains a subject of interest.

References

2023. Open science discovery of potent noncovalent SARS-CoV-2 main protease inhibitors. *Science (New York, N.Y.)*.
DOI: 10.1126/science.abo7201

2017. Discovery of multi-target receptor tyrosine kinase inhibitors as novel anti-angiogenesis agents. *Scientific Reports*.
DOI: 10.1038/srep45145

2016. Oxyfunctionalization of pyridine derivatives using whole cells of Burkholderia sp. MAK1. *Scientific Reports*.
DOI: 10.1038/srep39129