6-Bromo-2,3-difluoropyridine
[CAS# 1257071-45-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Fluoropyridine
• Name: 6-Bromo-2,3-difluoropyridine
• Molecular Formula: C₅H₂BrF₂N
• Molecular Weight: 193.98
• CAS Registry Number: 1257071-45-6
• SMILES: C1=CC(=NC(=C1F)F)Br

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.509, Calc.^*
• Boiling Point: 184.2±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 65.2±25.9 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06 Danger
• Hazard Statements: H301-H311-H331
• Precautionary Statements: P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501

Discovory and Applicatios

6-Bromo-2,3-difluoropyridine is a halogenated pyridine derivative that has attracted attention in various areas of chemical research and applications, particularly in the fields of medicinal chemistry and material science. Pyridine and its derivatives are important building blocks in organic chemistry due to their ability to participate in diverse reactions, making them valuable in both synthetic and applied chemistry.

The discovery of 6-bromo-2,3-difluoropyridine stems from the ongoing exploration of halogenated heterocyclic compounds for their enhanced properties in terms of chemical reactivity, stability, and biological activity. The combination of bromine and fluorine atoms in specific positions on the pyridine ring plays a significant role in modulating the electronic properties of the molecule, which is critical for its reactivity and interaction with various molecular targets.

In the context of its applications, 6-bromo-2,3-difluoropyridine is primarily used as an intermediate in the synthesis of more complex molecules, particularly in the pharmaceutical and agrochemical industries. Pyridine derivatives, including those with halogen substituents, are known for their ability to act as ligands for metal catalysts, which is particularly valuable in cross-coupling reactions and other catalytic processes. The halogen atoms enhance the reactivity of the pyridine ring, making 6-bromo-2,3-difluoropyridine a useful building block in the preparation of compounds with a wide range of biological and chemical activities.

One key application of 6-bromo-2,3-difluoropyridine is its use in the synthesis of biologically active molecules. The fluorine atoms in the structure introduce unique electronic effects that can influence the compound's pharmacokinetic properties, such as its ability to cross biological membranes and interact with specific receptors or enzymes. As a result, halogenated pyridines like 6-bromo-2,3-difluoropyridine have been investigated for their potential as leads in the development of novel therapeutics, particularly in areas like cancer, infectious diseases, and neurological disorders. The presence of bromine and fluorine atoms may also increase the metabolic stability of the molecules, which is a key factor in drug development.

Furthermore, the compound has found applications beyond the pharmaceutical industry. In materials science, 6-bromo-2,3-difluoropyridine has been explored for its potential in the design of electronic materials, such as organic semiconductors and conductive polymers. The presence of halogens can enhance the material's electronic properties, making it suitable for use in devices such as organic light-emitting diodes (OLEDs), organic solar cells, and flexible electronics. The compound's role as a precursor in these applications highlights the versatility of halogenated pyridine derivatives in the development of advanced materials.

In addition to its role in organic synthesis and materials science, 6-bromo-2,3-difluoropyridine is also of interest in agrochemical applications. Pyridine-based compounds are often employed in the synthesis of herbicides, pesticides, and fungicides due to their ability to interact with biological targets in plants and microorganisms. The halogenation of the pyridine ring can enhance the selectivity and potency of these compounds, improving their efficacy as agrochemicals.

Overall, the discovery and application of 6-bromo-2,3-difluoropyridine illustrate the significance of halogenated pyridine derivatives in modern chemical synthesis and industrial applications. With its unique structural features and versatile reactivity, this compound continues to be an important tool for the development of new pharmaceuticals, materials, and agrochemicals.