2-Cyanobenzyl Bromide (CAS: 22115-41-9) is a fine chemical intermediate that holds significant importance in various industrial applications, particularly within the pharmaceutical sector. Its unique molecular structure, combining a nitrile group with a reactive benzyl bromide, allows it to serve as a crucial building block for complex organic synthesis. This article aims to provide a comprehensive understanding of its chemical properties, synthesis, safe handling, and key applications.

Chemical Properties and Reactivity

The molecular formula for 2-Cyanobenzyl Bromide is C8H6BrN, with a molecular weight of approximately 196.04 g/mol. Typically supplied as a white to off-white solid, it exhibits a melting point in the range of 72-74°C. The compound's reactivity is primarily driven by the benzylic bromide functionality, which is susceptible to nucleophilic substitution reactions. This makes it an excellent electrophilic reagent for introducing the 2-cyanobenzyl group into other molecules. The nitrile group (-CN) offers additional possibilities for functional group transformations, such as reduction to an amine or hydrolysis to a carboxylic acid, further enhancing its utility in synthesis.

Synthesis and Manufacturing

The common synthetic route for 2-Cyanobenzyl Bromide involves the bromination of o-tolunitrile (2-methylbenzonitrile). This process typically employs radical bromination using reagents like N-bromosuccinimide (NBS) in the presence of a radical initiator such as azobisisobutyronitrile (AIBN) or under UV light. Solvents like carbon tetrachloride are often used. Ensuring high purity requires careful control of reaction conditions, efficient purification techniques (such as recrystallization or distillation), and robust quality control by manufacturers. Companies seeking to buy 2-Cyanobenzyl Bromide should look for suppliers who can guarantee consistent quality and purity levels, often specified as ≥98.0%.

Key Applications and Significance

The most prominent application of 2-Cyanobenzyl Bromide is its use as a critical intermediate in the synthesis of Alogliptin. Alogliptin is a dipeptidyl peptidase-4 (DPP-4) inhibitor used to treat type 2 diabetes. The structural features of 2-Cyanobenzyl Bromide are integral to building the pharmacologically active molecule of Alogliptin. Beyond this specific pharmaceutical application, 2-Cyanobenzyl Bromide serves as a versatile building block in general organic synthesis for creating novel compounds, specialty chemicals, and materials. Researchers and chemical engineers often source this compound for R&D projects involving complex molecular architectures.

Sourcing and Handling Information

When procuring 2-Cyanobenzyl Bromide, it is important to consider factors such as supplier reliability, packaging, and shipping. Many global suppliers, particularly from China, offer this compound with competitive 2-Cyanobenzyl Bromide prices. It's crucial to work with a reputable 2-Cyanobenzyl Bromide supplier that provides necessary safety data sheets (SDS) and adheres to proper handling and storage guidelines. Due to its reactive nature and potential for irritation, it should be handled in a well-ventilated area with appropriate personal protective equipment (PPE).

In conclusion, 2-Cyanobenzyl Bromide is a fundamental chemical intermediate with significant industrial value. Its well-defined properties and reactivity make it an indispensable tool for pharmaceutical synthesis and broader organic chemistry research. Understanding its characteristics and sourcing it from reliable manufacturers ensures successful application in advanced chemical projects.