2-Fluoro-5-bromopyridine
[CAS# 766-11-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Bromopyridine
• Name: 2-Fluoro-5-bromopyridine
• Synonyms: 5-Bromo-2-fluoropyridine; 3-Bromo-6-fluoropyridine
• Molecular Formula: C₅H₃BrFN
• Molecular Weight: 175.99
• CAS Registry Number: 766-11-0
• EC Number: 629-380-1
• SMILES: C1=CC(=NC=C1Br)F

Properties

• Density: 1.71
• Boiling point: 170-173 °C
• Refractive index: 1.531-1.533
• Flash point: 73 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2A	H319
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

2-Fluoro-5-bromopyridine is a heterocyclic aromatic compound that has garnered attention in the fields of medicinal chemistry and organic synthesis due to its unique reactivity and potential applications. This compound features a pyridine ring substituted with both fluorine and bromine atoms, which imparts distinct electronic properties, making it a valuable building block in the synthesis of various pharmaceuticals and agrochemicals.

The discovery of 2-fluoro-5-bromopyridine can be traced back to research focused on developing new methods for functionalizing aromatic compounds. The introduction of halogen atoms, particularly fluorine and bromine, into organic molecules is a well-established strategy for enhancing their biological activity. The presence of the fluorine atom not only improves the compound's metabolic stability but also influences its lipophilicity and ability to cross biological membranes, which are crucial factors in drug design.

One of the most significant applications of 2-fluoro-5-bromopyridine is in the synthesis of pharmaceutical intermediates. The bromine atom serves as a versatile handle for further chemical transformations, allowing for the introduction of various functional groups. For example, coupling reactions can be conducted using this compound as a precursor to synthesize more complex molecules that exhibit desired biological activity. Researchers have found that compounds derived from 2-fluoro-5-bromopyridine can possess potent activity against various biological targets, making them candidates for further exploration in drug development.

In addition to its pharmaceutical applications, 2-fluoro-5-bromopyridine is also utilized in the agrochemical industry. The compound can be employed in the synthesis of new herbicides and pesticides, which are essential for modern agriculture. The unique electronic properties imparted by the fluorine and bromine substituents can enhance the efficacy and selectivity of these agrochemicals, providing better crop protection while minimizing environmental impact. Research in this area is ongoing, with efforts aimed at developing safer and more effective agricultural products.

Furthermore, the compound has been investigated for its potential use in materials science. The ability to incorporate halogenated pyridines into polymer matrices can improve the thermal and mechanical properties of the resulting materials. The incorporation of 2-fluoro-5-bromopyridine into polymer systems may enhance flame retardancy, chemical resistance, and overall durability, making it suitable for various industrial applications.

Safety considerations are paramount when handling 2-fluoro-5-bromopyridine. Like many halogenated compounds, it may pose health risks if proper precautions are not taken. Appropriate safety measures, including the use of personal protective equipment and proper ventilation, should be implemented to minimize exposure during synthesis and application.

Research continues to explore the full potential of 2-fluoro-5-bromopyridine. Studies are being conducted to better understand its reactivity patterns and interactions with biological systems. As the demand for new pharmaceuticals and agrochemicals grows, the development of novel compounds based on 2-fluoro-5-bromopyridine will likely play a significant role in addressing contemporary challenges in health and agriculture.

In summary, 2-fluoro-5-bromopyridine is a valuable chemical substance with applications in pharmaceuticals, agrochemicals, and materials science. Its unique properties and reactivity make it a versatile building block for synthesizing a wide range of biologically active compounds. Ongoing research aims to further explore its potential and enhance its applications in various fields.

References

2022. 1,2-Additions on Chiral N-Sulfinylketimines: An Easy Access to Chiral α-Tertiary Amines. Synthesis, 54(5).
DOI: 10.1055/s-0041-1737563

2011. Efficient and Scalable Synthesis of Pyridine Sulfonamides. Synlett, 2011(7).
DOI: 10.1055/s-0030-1259953

2000. Ultraviolet absorption and vibrational spectra of 2-fluoro-5-bromopyridine. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 56(8).
DOI: 10.1016/s1386-1425(99)00275-9