What Is 2-Bromo-N-(3-pyridinyl)benzamide?

2-Bromo-N-(3-pyridinyl)benzamide (SKU: B1318976) is an organic compound featuring a benzamide core substituted with a bromine atom at the ortho position of the benzoyl ring and a 3-pyridinyl group on the nitrogen. Its molecular formula is C₁₂H₉BrN₂O with a molecular weight of approximately 277.12 g/mol.

The compound belongs to the class of N-aryl benzamides and combines two pharmacophore-relevant heterocyclic/aromatic motifs: an ortho-bromophenyl carbonyl group and a pyridine ring. This dual functionality makes it a versatile intermediate in organic synthesis, particularly in transition-metal-catalyzed coupling reactions and the construction of bioactive heterocyclic scaffolds.

Key Chemical Properties and Handling

The ortho-bromo substituent on the benzoyl ring serves as a reactive handle for palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig, and carbonylative coupling reactions. The amide nitrogen–hydrogen bond can also participate in directed C–H activation chemistry.

As with most organobromine compounds, 2-Bromo-N-(3-pyridinyl)benzamide should be handled with care. Appropriate personal protective equipment (PPE) including gloves, lab coat, and safety glasses should be worn at all times. Work should be conducted in a well-ventilated area or fume hood. The compound should be stored in a cool, dry location away from light and moisture to maintain stability and purity.

Compatibility with common organic solvents such as DMSO, DMF, dichloromethane, and ethyl acetate is generally expected for this class of compound, though solubility should be verified experimentally prior to use in sensitive assays.

Synthetic and Research Applications

2-Bromo-N-(3-pyridinyl)benzamide is primarily employed as a building block in medicinal chemistry and heterocyclic synthesis. The aryl bromide moiety enables efficient palladium- or nickel-catalyzed cross-coupling with boronic acids, amines, and other nucleophiles to generate structurally diverse biaryl amide libraries.

The pyridine nitrogen can act as a coordination site in metal-catalyzed reactions and also contributes to the aqueous solubility profile of resulting products—a desirable attribute in drug discovery programs. Compounds derived from N-(pyridinyl)benzamide scaffolds have been explored in research targeting kinases and other enzyme classes, although specific biological activity data for 2-Bromo-N-(3-pyridinyl)benzamide itself should be verified from primary literature.

Researchers in process chemistry may also use this compound as a reference standard or as a precursor in the preparation of more complex amide-containing pharmacophores.

Ordering and Quality Information

2-Bromo-N-(3-pyridinyl)benzamide is available from Aladdin Scientific under SKU B1318976. Researchers are encouraged to review the product specification sheet for confirmed purity, analytical data (such as HPLC or NMR), and lot-specific certificates of analysis (CoA) prior to placing an order.

For bulk quantities or custom purity grades, please contact Aladdin Scientific's sales team. Standard packaging is designed to maintain reagent integrity during shipping and short-term storage. Upon receipt, inspect the packaging for damage and store according to the label instructions.