Understanding the fundamental chemistry of crucial intermediates is vital for any researcher or developer aiming for successful synthesis. 3-Bromo-2-hydroxypyridine (CAS: 13466-43-8) is a prime example of such a compound, possessing a unique structure that dictates its reactivity and wide range of applications. From its synthesis to its tautomeric behavior and chemical transformations, a deeper appreciation of its properties can significantly aid in its effective utilization. For those looking to buy this compound, knowing its chemical characteristics is the first step.

Synthesis and Tautomerism: The Core Chemistry

The synthesis of 3-Bromo-2-hydroxypyridine typically involves the direct bromination of 2-pyridone. This process, often carried out using bromine in an aqueous solution, yields the desired product, which can then be purified through recrystallization. The compound exists in a tautomeric equilibrium between its 2-hydroxypyridine (enol) form and its 2-pyridone (keto) form. Spectroscopic evidence, particularly FTIR analysis showing a strong carbonyl (C=O) stretch, along with computational studies, confirms that the keto tautomer (3-bromo-2(1H)-pyridinone) is the predominant species in both solid state and solution. This tautomerism influences its reactivity and physical properties.

Reactivity and Applications in Synthesis

The presence of both a reactive bromine atom and a hydroxyl group, coupled with the electron distribution in the pyridine ring, endows 3-Bromo-2-hydroxypyridine with significant synthetic utility. The bromine atom is amenable to various cross-coupling reactions, such as Suzuki, Stille, or Sonogashira couplings, allowing for the introduction of diverse carbon-based substituents. The hydroxyl group can participate in esterification or etherification reactions, or act as a nucleophile after deprotonation. This dual functionality makes it an ideal starting material for building complex heterocyclic frameworks.

These reactivity patterns are critical for its application in pharmaceutical research, where it serves as an intermediate for creating drug candidates like pyrazolopyridines. In agrochemical synthesis, it helps in constructing molecules with targeted biological activity. For researchers looking to buy this compound for their synthesis needs, its predictable reactivity ensures a reliable pathway to desired end products.

Quality and Sourcing from a Manufacturer

As a key intermediate, the purity and consistent quality of 3-Bromo-2-hydroxypyridine are paramount. Manufacturers often subject the compound to rigorous quality control measures, ensuring high purity levels (e.g., ≥97% or ≥99% by HPLC). When sourcing, looking for suppliers who provide comprehensive technical data, including spectroscopic evidence of structure and purity, is essential. Direct engagement with manufacturers offers transparency regarding production processes and quality assurance, making it easier to buy with confidence.

Understanding the synthesis, tautomerism, and reactivity of 3-Bromo-2-hydroxypyridine (CAS 13466-43-8) empowers researchers to harness its full potential. By partnering with reliable suppliers for this vital building block, innovation in chemical synthesis can be effectively driven forward.