Overview
5-Bromo-2-chloropyridine is a halogenated heterocyclic compound serving as a versatile building block in organic synthesis. The molecular structure combines reactive bromine and chlorine substituents on a pyridine ring, enabling diverse functionalization through transition metal-catalyzed cross-couplings. Developed in the late 20th century, this intermediate has become essential for manufacturing active pharmaceutical ingredients (APIs) and crop protection agents. Commercial production typically involves direct halogenation of pyridine derivatives or multi-step synthesis from halogenated precursors. The compound's reactivity stems from the differential substitution pattern, where the bromine at position 5 participates readily in Suzuki-Miyaura couplings, while the chlorine at position 2 offers alternative modification pathways.
Physical and Chemical Properties
This crystalline solid exhibits moderate stability under dry conditions but may decompose when exposed to moisture or strong acids/bases. The bromine and chlorine substituents create an electron-deficient aromatic system, making the compound less basic than unsubstituted pyridine. Characteristic IR absorption occurs at 680 cm⁻¹ (C-Br stretch) and 540 cm⁻¹ (C-Cl stretch). In solution, 5-bromo-2-chloropyridine shows UV-Vis absorption maxima at 265 nm (ε ≈ 4,200 L/mol·cm). The compound's partition coefficient (log P) of 2.3 indicates moderate lipophilicity, influencing its solubility profile and reactivity in organic media. Thermal analysis reveals decomposition above 200°C, necessitating careful handling during high-temperature reactions.
Main Applications
Approximately 70% of global production serves pharmaceutical synthesis, particularly for kinase inhibitor drugs and antiviral compounds. The bromine substituent enables efficient palladium-catalyzed couplings to construct biaryl structures found in numerous FDA-approved medications. In agrochemicals, it functions as a precursor for fungicides and herbicides that target fungal CYP51 enzymes. Emerging applications include organic electronics, where the compound acts as a halogenated precursor for conductive polymers. Research-grade usage spans coordination chemistry (ligand synthesis) and radiopharmaceutical labeling (bromine-76 isotope). Recent patent literature highlights its incorporation into OLED materials and photovoltaic sensitizers.
Safety and Storage
Classified as harmful (Xn) under EU regulations, the compound requires handling in well-ventilated areas with appropriate personal protective equipment. Powdered form presents inhalation risks—use fume hoods during weighing. Spills should be contained with inert absorbents and disposed as halogenated waste. Long-term storage demands moisture-proof containers (preferably amber glass) under nitrogen atmosphere. Technical specifications recommend ≤3 years shelf life when stored at 2-8°C. Commercial shipments typically include oxygen scavengers and desiccants. Bulk transportation follows UN2811 (toxic solids, organic) regulations with proper hazard labeling.
B2B Procurement Guide
Industrial buyers should prioritize suppliers with ISO 9001-certified production facilities and batch-to-batch consistency guarantees. Key evaluation parameters include HPLC purity (≥98%), residual solvent levels (≤500 ppm), and heavy metal content (≤10 ppm). Request certificates of analysis (CoA) with detailed impurity profiles. Procurement strategies should consider multi-kilogram contracts for cost efficiency—typical MOQs range 5-25kg. Spot prices fluctuate based on bromine commodity markets. Preferred packaging includes double-lined PE bags inside fiber drums. For international shipments, verify compliance with destination country regulations (e.g., REACH, TSCA). Technical samples (100-500g) are often available for R&D evaluation.
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