In the intricate world of chemical synthesis, intermediates play a pivotal role, acting as crucial stepping stones to complex molecules. 5-Bromo-2-hydroxypyridine (CAS 13466-38-1), also known by its tautomeric form 5-Bromo-2-pyridone, is a prominent example of such an indispensable intermediate. Its unique chemical structure, featuring a bromine substituent and a hydroxyl group on a pyridine ring, makes it a versatile building block for a wide array of applications, particularly in the pharmaceutical, dye, and agrochemical industries. For chemical manufacturers and formulation scientists, understanding its synthesis and applications is key to leveraging its full potential.

Synthetic Routes to 5-Bromo-2-hydroxypyridine

The synthesis of 5-Bromo-2-hydroxypyridine often involves electrophilic substitution reactions on 2-hydroxypyridine. A common method includes the direct bromination of 2-hydroxypyridine using brominating agents like N-bromosuccinimide (NBS) or elemental bromine under controlled conditions. The reaction typically proceeds efficiently, yielding the desired product with good regioselectivity at the 5-position due to the activating effect of the hydroxyl group and the directing influence of the nitrogen atom. Alternative synthetic strategies might involve palladium-catalyzed cross-coupling reactions or functional group transformations starting from other brominated pyridine derivatives. Manufacturers often optimize these processes for yield, purity, and scalability, ensuring a reliable supply for their clients.

Key Applications Across Industries

The versatility of 5-Bromo-2-hydroxypyridine stems from its ability to participate in various coupling reactions, nucleophilic substitutions, and other transformations. Its primary applications include:

  • Pharmaceutical Intermediates: It serves as a critical building block in the synthesis of numerous Active Pharmaceutical Ingredients (APIs). Its pyridine core is a common motif in many biologically active molecules, making it a valuable starting material for drug discovery and development. Procurement of high-purity material is essential when you buy for pharmaceutical synthesis.
  • Dye Intermediates: The compound is utilized in the production of specialty dyes and pigments. Its structure can be incorporated into chromophores to achieve specific colors and properties, making it a sought-after component for dye manufacturers.
  • Agrochemical Intermediates: In the agrochemical sector, 5-Bromo-2-hydroxypyridine is employed in the synthesis of pesticides, herbicides, and other crop protection agents. Its incorporation can lead to compounds with improved efficacy and targeted action.
  • Flavors and Fragrances: Its unique chemical profile also lends itself to applications in the flavor and fragrance industry, where it can be used to synthesize specific aroma compounds.

Sourcing and Quality Considerations for Manufacturers

For chemical manufacturers looking to procure 5-Bromo-2-hydroxypyridine, partnering with reliable suppliers is paramount. Emphasis should be placed on obtaining material with a guaranteed purity of ≥98.0%, typically supplied as an off-white to yellow-brown crystalline powder. Understanding the CAS number (13466-38-1) and common synonyms is vital for an effective search. Obtaining detailed Certificates of Analysis (CoA) and Material Safety Data Sheets (MSDS) from suppliers is standard practice to ensure quality and safety. Companies in China are often key sources, offering competitive pricing for bulk orders, which is critical for large-scale manufacturing.

By thoroughly understanding the synthesis pathways and the diverse applications of 5-Bromo-2-hydroxypyridine, chemical manufacturers can effectively integrate this intermediate into their production processes, driving innovation and delivering high-quality products to the market.