Physical and Chemical Properties

2-Bromo-3-pyridinol (CAS 6602-32-0) is a bifunctionally substituted pyridine bearing a bromine atom at the 2-position and a hydroxyl group at the 3-position of the ring. Its molecular formula is C₅H₄BrNO with a molecular weight of approximately 174.00 g/mol. The compound typically presents as a white to off-white crystalline solid at room temperature.

The hydroxyl group in 2-Bromo-3-pyridinol exhibits partial phenolic character due to the adjacent ring nitrogen, resulting in a tautomeric equilibrium between the 3-hydroxy (pyridinol) and 3-oxo (pyridinone) forms. This tautomerism is an important consideration when planning reactions involving this scaffold. The compound is moderately soluble in polar organic solvents such as methanol, ethanol, dimethyl sulfoxide (DMSO), and tetrahydrofuran (THF), and sparingly soluble in non-polar solvents.

The aryl C–Br bond at the 2-position is well-suited for oxidative addition into palladium(0) and other transition-metal catalysts, making this compound a reactive partner in a variety of metal-catalyzed transformations.

Safe Handling and Storage Guidelines

Personal Protective Equipment (PPE): Always handle 2-Bromo-3-pyridinol wearing appropriate laboratory PPE, including chemical-resistant gloves (nitrile recommended), safety goggles or a face shield, and a laboratory coat. Operations generating dust or aerosols should be conducted in a well-ventilated fume hood.

Storage: Store the compound at 2–8 °C in a tightly sealed container, protected from light, heat, and atmospheric moisture. Exposure to moisture may promote hydrolysis or degradation over time. Keep the reagent away from strong oxidizing agents, strong bases, and reactive metals. Under recommended storage conditions, the compound is stable for the duration stated on the certificate of analysis.

Waste Disposal: Dispose of waste material containing 2-Bromo-3-pyridinol in accordance with institutional, local, and national regulations governing halogenated organic waste. Do not pour down the drain. Consult the Safety Data Sheet (SDS) available from Aladdin Scientific for complete hazard classification, first-aid measures, and regulatory information before use.

First Aid: In case of skin or eye contact, flush immediately with copious water for at least 15 minutes and seek medical attention. If inhaled, remove the affected person to fresh air. Refer to the SDS for full emergency procedures.

Synthetic Applications and Reaction Protocols

Palladium-Catalyzed Cross-Coupling: The aryl bromide moiety of 2-Bromo-3-pyridinol is reactive in standard Pd-catalyzed cross-coupling protocols. It can participate in Suzuki–Miyaura coupling with aryl- or heteroarylboronic acids to install diverse carbon substituents at the 2-position, in Sonogashira coupling with terminal alkynes, and in Buchwald–Hartwig amination to introduce nitrogen-containing groups. Typical conditions employ Pd(PPh₃)₄ or Pd(dppf)Cl₂ as catalyst, an appropriate base (e.g., K₂CO₃ or Cs₂CO₃), and a polar solvent system such as DMF/water or dioxane/water, at temperatures ranging from 80–110 °C.

O-Alkylation and O-Arylation: The 3-hydroxy group can be selectively alkylated using alkyl halides under basic conditions (e.g., K₂CO₃ in acetone or DMF) to afford 3-alkoxy-2-bromopyridine derivatives, which are useful precursors for further coupling chemistry. Care should be taken to avoid N-alkylation, which may occur depending on the tautomeric form predominating under reaction conditions.

Directed Metalation and Functionalization: The combination of a directing hydroxyl group and the ring nitrogen makes 2-Bromo-3-pyridinol a substrate amenable to directed ortho-metalation strategies after appropriate protection of the OH group, enabling further regioselective functionalization of the ring.

Medicinal Chemistry Applications: This compound serves as a key building block for the preparation of bioactive heterocyclic scaffolds, including kinase inhibitor cores, antibacterial agents, and other pharmacologically relevant pyridine derivatives. Its dual functionality allows divergent synthetic routes from a single starting material.

Quality, Purity and Analytical Verification

Purity Assessment: Aladdin Scientific's 2-Bromo-3-pyridinol (SKU: B110249) is supplied with a Certificate of Analysis (CoA) specifying purity determined by HPLC or GC analysis. Researchers should consult the CoA for the specific lot-level purity data prior to use in sensitive synthetic or biological assays.

Identity Confirmation: The identity of 2-Bromo-3-pyridinol can be confirmed by the following analytical techniques: (1) ¹H NMR spectroscopy — characteristic signals for the three aromatic ring protons and the exchangeable OH proton; (2) ¹³C NMR spectroscopy — signals consistent with the substituted pyridine carbon framework; (3) Mass spectrometry — molecular ion cluster at m/z 173/175 reflecting the natural isotope pattern of one bromine atom; (4) IR spectroscopy — broad O–H stretch (~3200–3400 cm⁻¹) and C–Br stretch bands.

Melting Point: The melting point can serve as a rapid purity indicator; consult the current CoA for the specified value. Significant deviation from the stated range may indicate degradation or contamination.

Handling High-Sensitivity Applications: For use in sensitive catalytic reactions, ensure that the reagent is fully dried if moisture-sensitive conditions are required. Dissolve in anhydrous solvent under inert atmosphere (N₂ or Ar) immediately before use when necessary.

Ordering, Packaging and Technical Support

Ordering: 2-Bromo-3-pyridinol is available from Aladdin Scientific under SKU B110249. Orders can be placed through the Aladdin Scientific online portal, by contacting your regional sales representative, or via authorized distributors. Bulk and custom quantities may be available upon request — please contact the Aladdin Scientific sales team for quotation.

Packaging: The compound is packaged under conditions designed to maintain stability during transit. Standard packaging options are listed on the product page. For long-distance or international shipments, the material is dispatched with appropriate cold-chain provisions to preserve product integrity.

Certificate of Analysis and Safety Data Sheet: A lot-specific CoA and a current SDS are available for download from the Aladdin Scientific product page for B110249, or upon request from customer service. Researchers are advised to review both documents before handling the material.

Technical Support: For application-specific guidance, compatibility questions, or custom synthesis inquiries, contact Aladdin Scientific's technical support team. Our scientific staff can advise on reaction conditions, compatible reagents, and formulation strategies tailored to your research needs.