Chemical Identity and Structure

Benzyl 5-bromopyridin-3-ylcarbamate (SKU B186471) is an organic compound with molecular formula C₁₃H₁₁BrN₂O₂ and a molecular weight of approximately 307.14 g/mol. The molecule consists of a pyridine ring bearing a bromo substituent at the 5-position and a benzyloxycarbonyl (Cbz)-protected amino group at the 3-position. The aryl bromide moiety serves as a reactive handle for metal-catalyzed coupling reactions, while the Cbz group protects the amine from undesired side reactions during multistep synthesis. This combination of orthogonal functional groups makes the compound particularly valuable as a bifunctional building block in complex molecule assembly.

Synthetic Applications and Reactivity

The aryl C–Br bond in Benzyl 5-bromopyridin-3-ylcarbamate undergoes a broad range of palladium- and copper-catalyzed cross-coupling transformations, including Suzuki–Miyaura (boronic acid coupling), Buchwald–Hartwig (C–N bond formation), Negishi, and Sonogashira reactions. These reactions allow introduction of diverse carbon or heteroatom substituents at the 5-position of the pyridine ring, enabling rapid generation of analogue libraries in medicinal chemistry programs.

The Cbz carbamate protecting group is stable under most standard coupling conditions (basic aqueous workup, mild Lewis acid conditions) and is selectively removed by catalytic hydrogenolysis (H₂, Pd/C) to unmask the free 3-aminopyridine, which may then be further functionalized. This orthogonal deprotection strategy is widely used in the synthesis of aminopyridine-containing drug candidates.

Handling, Storage, and Safety

As with all organobromine compounds and carbamate derivatives, Benzyl 5-bromopyridin-3-ylcarbamate should be handled with appropriate personal protective equipment, including nitrile gloves, a laboratory coat, and safety glasses. Work in a well-ventilated fume hood is recommended. The compound should be stored in a tightly sealed container at room temperature or under refrigeration (2–8 °C) away from moisture, light, and incompatible oxidizing agents to ensure long-term stability.

Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific prior to use for complete hazard classification, first-aid measures, and disposal guidance. Waste should be disposed of in accordance with applicable local and institutional regulations for halogenated organic compounds.

Purity, Quality, and Regulatory Information

Aladdin Scientific supplies Benzyl 5-bromopyridin-3-ylcarbamate (B186471) as a research-grade reagent. Purity is verified by standard analytical methods such as HPLC and NMR spectroscopy. A Certificate of Analysis (CoA) is available for each lot and provides specific purity values, analytical data, and lot-specific testing results. Researchers requiring material for GMP or clinical applications should contact Aladdin Scientific's technical team to discuss suitable grades and documentation.

This product is intended for research and development use only and is not approved for human or veterinary therapeutic applications.