Chemical Identity and Physical Properties

5-Bromo-2-(tert-butoxy)pyridine (SKU B726539) is a substituted pyridine bearing a bromine atom at the 5-position and a tert-butoxy group at the 2-position. Its molecular formula is C₉H₁₂BrNO with a molecular weight of approximately 230.10 g/mol. The compound is typically presented as a pale-yellow to off-white solid or liquid depending on purity and temperature. The electron-donating tert-butoxy substituent at the 2-position modulates the electron density of the pyridine ring, influencing both the reactivity of the aryl–bromide bond toward oxidative addition and the regioselectivity of downstream transformations. The tert-butoxy group also serves as a protecting group strategy for hydroxypyridine intermediates, enabling selective deprotection under acidic conditions when required.

Note: Precise physical constants (melting point, boiling point, density) should be confirmed from the current certificate of analysis (CoA) supplied with each lot from Aladdin Scientific.

Synthetic Applications and Reactivity

5-Bromo-2-(tert-butoxy)pyridine is a highly valued building block in modern organic and medicinal chemistry for the following key reasons:

• Palladium-Catalyzed Cross-Coupling: The aryl bromide moiety undergoes efficient Suzuki–Miyaura, Negishi, Buchwald–Hartwig, and Sonogashira coupling reactions under standard palladium catalysis conditions. These transformations enable rapid diversification of the pyridine scaffold for SAR exploration.
• Directed Metalation: The combined directing effects of the ring nitrogen and the 2-tert-butoxy group can facilitate directed ortho-metalation strategies, providing access to multiply substituted pyridine intermediates.
• Protecting Group Chemistry: The tert-butoxy group functions as an acid-labile protecting group for 2-hydroxypyridine (2-pyridinone tautomer). Selective cleavage using trifluoroacetic acid (TFA) or similar Brønsted acids liberates the free hydroxypyridine, a motif frequently encountered in bioactive molecules and drug candidates.
• Pharmaceutical Intermediate Synthesis: Pyridine-based scaffolds bearing ether substituents are recurrent motifs in kinase inhibitors, CNS agents, and other therapeutic classes, making this compound a strategic intermediate in drug discovery workflows.

Researchers should optimize catalyst loading, ligand selection, base, and solvent system for each specific transformation to achieve optimal yield and selectivity.

Safe Handling, Storage, and Disposal

As with all fine chemical reagents, appropriate laboratory safety practices must be observed when working with 5-Bromo-2-(tert-butoxy)pyridine. Researchers should consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific prior to use.

Handling

• Use in a well-ventilated fume hood to minimize inhalation exposure.
• Wear appropriate personal protective equipment (PPE): chemical-resistant gloves, safety goggles, and a laboratory coat.
• Avoid contact with skin, eyes, and mucous membranes.
• Wash hands thoroughly after handling.

Storage

• Store in a tightly sealed container in a cool, dry, and well-ventilated area.
• Keep away from direct sunlight, moisture, and incompatible materials (strong oxidizers, strong acids).
• Follow the storage temperature range specified on the product label and CoA.

Disposal

• Dispose of waste material in accordance with local, regional, and national regulations governing halogenated organic compounds.
• Do not pour down the drain or into the environment.

Always refer to the current Aladdin Scientific SDS for hazard classification, first-aid measures, and emergency response information specific to lot B726539.

Quality Specifications and Ordering Information

Aladdin Scientific supplies 5-Bromo-2-(tert-butoxy)pyridine (SKU: B726539) to meet the demands of research and development applications. Key quality attributes typically assessed include:

• Purity: Determined by GC or HPLC analysis; refer to the CoA for the specific lot purity value.
• Identity Confirmation: Verified by ¹H NMR and/or MS consistent with the target structure.
• Appearance: Visual inspection per internal specification.

Researchers requiring custom quantities, bulk pricing, or specific purity grades are encouraged to contact Aladdin Scientific's technical sales team. Lot-specific CoAs and SDS documents are available upon request or through the Aladdin online portal.

To order: Reference SKU B726539 when placing orders through the Aladdin Scientific website or authorized distributors.