2-Hydroxy-5-bromopyridine

2-Hydroxy-5-bromopyridine (CAS 13466-38-1) is a strategically functionalized pyridine scaffold engineered for pharmaceutical intermediate synthesis, cross-coupling reactions, and heterocyclic diversification . This molecule exists in tautomeric equilibrium between the 2-hydroxypyridine and 2-pyridone forms, integrating a bromine substituent at the C5 position of the pyridine ring. The C5-bromo handle is activated for Pd-catalyzed cross-coupling (Suzuki, Buchwald-Hartwig, Sonogashira) while the 2-hydroxy/oxo group enables hydrogen-bonding interactions and serves as a handle for etherification or alkylation . The compound features an electron-rich C-5 position that enables selective copper-catalyzed C–N bond formation with amines, heterocycles, and amides under mild conditions using inexpensive 1,2-diol ligands such as ethylene glycol . This intermediate is particularly valuable for constructing pharmaceutical actives, agrochemical ingredients, and functional materials where the 2-hydroxy-5-bromo motif enables modular synthetic strategies. Manufactured under controlled conditions, it supports drug discovery and chemical development programs requiring access to functionalized pyridine architectures