Chemical Identity and Structure

5-Bromo-N,N-diethylpicolinamide belongs to the picolinamide family of heterocyclic compounds. Its structure consists of a pyridine ring bearing a bromine substituent at the 5-position and a diethylcarboxamide group at the 2-position (picolinic acid position). This combination of an electrophilic C–Br bond and a coordinating amide moiety on the same ring makes the compound a bifunctional building block suitable for a variety of synthetic transformations.

The C5 carbon–bromine bond is well-suited for oxidative addition into palladium(0) and nickel(0) catalytic cycles, enabling participation in palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig couplings. Simultaneously, the 2-carboxamide group can serve as a directing group in transition-metal-mediated C–H functionalization or as a ligand-binding motif in coordination chemistry.

The N,N-diethyl substitution on the amide nitrogen increases steric bulk around the carbonyl, reducing susceptibility to hydrolysis relative to primary or secondary amides, and modulating the electronic character of the pyridine ring.

Physicochemical Properties and Purity

As a member of the brominated picolinamide class, 5-Bromo-N,N-diethylpicolinamide is typically a white to off-white crystalline solid at room temperature. Key physicochemical attributes relevant to laboratory use include its molecular formula C₁₀H₁₃BrN₂O and a molecular weight of approximately 257.13 g/mol.

The compound displays moderate lipophilicity due to the diethylamino substituents combined with the polar amide carbonyl, influencing its solubility profile: it is generally soluble in common organic solvents such as dichloromethane, tetrahydrofuran, dimethyl sulfoxide (DMSO), and ethyl acetate, and sparingly soluble in water. Researchers should verify solubility empirically for their specific application conditions.

For synthetic applications demanding high-fidelity coupling outcomes, purity is a critical parameter. Aladdin Scientific supplies this compound under SKU B730902; users are advised to consult the accompanying Certificate of Analysis (CoA) for confirmed purity data, melting point, and spectral characterization prior to use.

Note: Specific purity percentage and exact melting point values are not stated in the current source material; please refer to the product CoA or contact Aladdin Scientific for batch-specific data.

Laboratory Applications and Synthetic Utility

5-Bromo-N,N-diethylpicolinamide is valued primarily as a synthetic intermediate in medicinal chemistry, agrochemical research, and materials science. Its principal applications include:

• Palladium-catalyzed cross-coupling: The aryl C–Br bond undergoes efficient Suzuki–Miyaura coupling with arylboronic acids and esters, Negishi coupling with organozinc reagents, and Sonogashira coupling with terminal alkynes to install diverse substituents at the 5-position of the pyridine ring.
• Buchwald–Hartwig amination: The C–Br bond can be converted to C–N bonds under palladium catalysis, enabling access to aminopyridine derivatives.
• Directed ortho-metalation: The 2-carboxamide group can act as a directed metalation group (DMG), facilitating regioselective lithiation or other metalations at positions ortho to the directing group for further functionalization.
• Scaffold diversification in drug discovery: Picolinamide scaffolds frequently appear in bioactive molecules and pharmaceutical candidates; this compound provides a pre-functionalized entry point for library synthesis.

Researchers should optimize catalyst loadings, ligands, bases, solvents, and temperatures for their specific coupling protocols, as optimal conditions vary significantly depending on coupling partners and desired products.

Safe Handling, Storage, and Disposal

Personal Protective Equipment (PPE): Always handle 5-Bromo-N,N-diethylpicolinamide wearing appropriate PPE including chemical-resistant gloves, a laboratory coat, and safety glasses or goggles. Operations that generate dust or aerosols should be conducted in a well-ventilated fume hood to minimize inhalation exposure.

Storage: Store the compound in a tightly sealed container in a cool, dry, well-ventilated area, away from direct light, heat sources, and moisture. Segregate from strong oxidizers and reactive reagents. Keep the container closed when not in use to prevent moisture uptake and degradation.

Stability: As with most organobromine compounds, prolonged exposure to air, moisture, or elevated temperatures may lead to gradual decomposition. Verify compound integrity by checking appearance and, where warranted, running an NMR or HPLC analysis before use in critical experiments.

Disposal: Dispose of waste material in accordance with local, regional, and national regulations governing halogenated organic waste. Do not dispose of via drain, sewer, or general waste streams. Consult your institution's Environmental Health and Safety (EHS) office for approved disposal procedures.

Note: A full Safety Data Sheet (SDS) should be consulted for comprehensive hazard, first-aid, and regulatory information specific to this compound. Contact Aladdin Scientific for the current SDS.