3-Bromo-4-chloro-5-nitropyridine
[CAS# 31872-63-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Nitropyridine
• Name: 3-Bromo-4-chloro-5-nitropyridine
• Synonyms: 3-Nitro-4-chloro-5-bromopyridine
• Molecular Formula: C₅H₂BrClN₂O₂
• Molecular Weight: 237.44
• CAS Registry Number: 31872-63-6
• EC Number: 689-449-7
• SMILES: C1=C(C(=C(C=N1)Br)Cl)[N+](=O)[O-]

Properties

• Density: 1.936
• Melting point: 49-50 °C
• Boiling point: 285 °C
• Flash point: 126 °C

Safety Data

• Hazard Symbols: GHS05;GHS06 Danger
• Risk Statements: H301-H318
• Safety Statements: P264-P264+P265-P270-P280-P301+P316-P305+P351+P338-P321-P330-P337+P317-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

3-Bromo-4-chloro-5-nitropyridine is a significant heterocyclic compound that has garnered attention in the fields of organic chemistry and medicinal chemistry due to its diverse applications. This compound belongs to the pyridine family, which is known for its aromatic properties and presence in various biologically active molecules. The unique combination of halogen and nitro substituents on the pyridine ring contributes to its reactivity and potential usefulness in synthetic pathways and pharmaceutical developments.

The discovery of 3-bromo-4-chloro-5-nitropyridine can be traced back to the systematic exploration of halogenated pyridine derivatives, which have been the subject of extensive research since the early 20th century. The incorporation of bromine, chlorine, and nitro groups into the pyridine framework significantly enhances the compound's chemical properties. These substitutions can modify the electronic characteristics of the molecule, influencing its behavior in chemical reactions and interactions with biological targets.

The synthesis of 3-bromo-4-chloro-5-nitropyridine typically involves multiple steps, often starting from commercially available pyridine derivatives. Common synthetic routes may include halogenation reactions and nitration procedures. For instance, the introduction of bromine and chlorine can be achieved through electrophilic aromatic substitution, while the nitro group is generally added via nitration reactions. These synthetic strategies not only yield the desired compound but also facilitate the exploration of structural modifications to optimize biological activity.

In terms of applications, 3-bromo-4-chloro-5-nitropyridine has demonstrated potential in various fields, particularly in medicinal chemistry. The presence of the nitro group is particularly noteworthy, as it can act as a bioisostere for other functional groups, allowing for the design of molecules with improved pharmacological properties. Additionally, halogenated pyridines, including 3-bromo-4-chloro-5-nitropyridine, have been investigated for their activity against a range of biological targets, including antimicrobial and anticancer agents.

Research has shown that 3-bromo-4-chloro-5-nitropyridine exhibits significant biological activity, making it a valuable compound for drug discovery. Its ability to interact with various enzymes and receptors in biological systems opens avenues for the development of new therapeutic agents. The unique combination of halogen and nitro groups may enhance the compound's selectivity and potency, making it a candidate for further investigation in the treatment of diseases.

Moreover, the reactivity of 3-bromo-4-chloro-5-nitropyridine allows it to serve as an important intermediate in the synthesis of more complex organic molecules. Its functional groups can participate in a variety of chemical reactions, including nucleophilic substitutions and coupling reactions, leading to the formation of novel compounds with potential applications in various domains.

In summary, 3-bromo-4-chloro-5-nitropyridine is a versatile compound with significant importance in organic and medicinal chemistry. Its unique structure and reactivity contribute to its potential as a building block for the synthesis of biologically active molecules. As research continues to explore its applications, this compound may play a crucial role in the development of new drugs and therapeutic strategies.

References

1979. Azaindole derivatives. Chemistry of Heterocyclic Compounds, 15(1).
DOI: 10.1007/bf00471204