Overview
2,6-Dibromopyridine is a brominated derivative of pyridine, characterized by two bromine atoms at the 2 and 6 positions of the aromatic ring. It serves as a versatile intermediate in organic synthesis, particularly in the pharmaceutical and agrochemical industries. The compound's reactivity in cross-coupling reactions (e.g., Suzuki, Stille) makes it valuable for constructing complex molecular frameworks. Due to its electron-withdrawing bromine substituents, 2,6-dibromopyridine exhibits modified electronic properties compared to pyridine, enabling selective functionalization. It is typically supplied as a crystalline solid with high purity (≥98%) for industrial applications.
Physical and Chemical Properties
2,6-Dibromopyridine is a white to off-white crystalline powder with a melting point range of 49-53°C. It is soluble in common organic solvents like ethanol, acetone, and dichloromethane but exhibits negligible solubility in water. The bromine atoms impart stability to the molecule, though it remains sensitive to strong reducing agents and extreme pH conditions. The compound's molecular weight is 236.89 g/mol, and its structure is confirmed by spectroscopic methods (NMR, IR). Its reactivity is dominated by the bromine sites, which participate in metal-catalyzed coupling reactions, nucleophilic substitutions, and ligand formation for transition-metal complexes.
Main Applications
In pharmaceuticals, 2,6-dibromopyridine is a key intermediate for synthesizing active ingredients, including antiviral and anticancer agents. Its role in Suzuki-Miyaura couplings facilitates the construction of biaryl motifs found in many drugs. Agrochemical manufacturers use it to produce herbicides and fungicides with enhanced efficacy. The compound also finds niche applications in material science, such as the preparation of conductive polymers and ligands for catalytic systems. Its ability to coordinate with metals (e.g., palladium, platinum) makes it useful in homogeneous catalysis and OLED material development.
Safety and Storage
2,6-Dibromopyridine is classified as an irritant and should be handled with gloves, goggles, and fume hoods to avoid skin/eye contact or inhalation. Spills should be contained with inert absorbents and disposed of as hazardous waste. It is stable under ambient conditions but may decompose if exposed to strong acids, bases, or oxidizers. Storage requires a tightly sealed container in a cool, dry environment away from light. Compatibility with common lab materials (e.g., glass, HDPE) is high, but prolonged contact with metals should be avoided to prevent unwanted reactions.
B2B Procurement Guide
When procuring 2,6-dibromopyridine, prioritize suppliers with ISO certification and batch-specific COAs (Certificates of Analysis) to ensure purity (≥98%) and traceability. Key specifications include residual solvent levels, heavy metal content, and particle size distribution for specialized applications. Bulk buyers should negotiate MOQs (Minimum Order Quantities) and lead times, as custom synthesis may be required. Spot prices fluctuate based on bromine market trends; long-term contracts can mitigate cost volatility. Logistics must comply with hazardous material regulations for safe transportation.
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