In the intricate world of organic chemistry, certain molecular structures stand out for their versatility and impact on synthetic pathways. 2-(4-Bromophenyl)pyridine (CAS: 63996-36-1) is one such compound, a valuable pyridine derivative that acts as a cornerstone in the construction of complex organic molecules. This article explores its chemical backbone, reactivity, and significance in contemporary synthesis, highlighting its importance for researchers and manufacturers seeking to buy this essential intermediate.

Molecular Structure and Key Features

At its core, 2-(4-Bromophenyl)pyridine is a bicyclic structure where a pyridine ring is directly attached at its 2-position to a phenyl ring that is substituted with a bromine atom at the para (4-) position. This arrangement is critical to its utility:

  • Pyridine Ring: The nitrogen atom in the pyridine ring imparts basicity and offers sites for Lewis acid coordination or hydrogen bonding. It influences the electron distribution across the molecule and can direct regioselectivity in certain reactions.
  • Bromophenyl Group: The presence of bromine on the phenyl ring is arguably its most synthetically useful feature. Bromine is an excellent leaving group in palladium-catalyzed cross-coupling reactions, a cornerstone of modern organic synthesis for forming C-C, C-N, and C-O bonds.

Typically supplied as a white powder with a melting point between 61-65℃ and a purity of at least 97%, this compound is designed for high-performance synthesis. Manufacturers, especially those in China, ensure this quality through rigorous analytical testing.

Reactivity and Synthetic Transformations

The dual nature of its functional groups makes 2-(4-Bromophenyl)pyridine exceptionally versatile. Its most exploited reactivity involves the aryl bromide:

  • Suzuki-Miyaura Coupling: Reacting with boronic acids or esters in the presence of a palladium catalyst, allowing the introduction of various aryl, vinyl, or alkyl groups at the para position of the phenyl ring.
  • Heck Reaction: Coupling with alkenes to form substituted styrenes or related structures.
  • Sonogashira Coupling: Reacting with terminal alkynes to introduce alkyne functionalities.
  • Buchwald-Hartwig Amination: Forming C-N bonds by reacting with amines.

The pyridine nitrogen can also be quaternized or form complexes with transition metals, enabling its use as a ligand in catalysis or as a component in coordination polymers.

Applications Across Industries

The primary demand for 2-(4-Bromophenyl)pyridine comes from the pharmaceutical industry, where it serves as a key intermediate in the synthesis of drug candidates targeting a wide range of diseases. Its structural motif can be found in molecules being investigated for their efficacy as kinase inhibitors, receptor modulators, and more. Beyond pharmaceuticals, its utility extends to materials science for creating novel organic semiconductors, luminescent materials, and liquid crystals. Researchers looking to buy this compound for innovative projects can rely on specialized chemical suppliers for consistent quality and availability.

In essence, 2-(4-Bromophenyl)pyridine is a foundational molecule that enables the creation of sophisticated organic architectures, driving progress in chemistry and its applied fields.