Chemical Abstract Service (CAS) numbers are unique identifiers crucial for the precise referencing of chemical substances. CAS No. 301652-23-3 refers to 4-Methyl-2-(tributylstannyl)pyridine, an organometallic compound that plays a significant role as an intermediate in various chemical synthesis pathways. Understanding its properties and applications is vital for researchers and procurement professionals in the chemical and pharmaceutical industries.

Chemical Identity and Structure:

4-Methyl-2-(tributylstannyl)pyridine is characterized by its molecular formula C18H33NSn and a molecular weight of approximately 382.16 g/mol. The molecule consists of a pyridine ring substituted with a methyl group at the 4-position and a tributylstannyl group (-Sn(n-Bu)₃) at the 2-position. This organotin moiety is key to its reactivity, particularly in carbon-carbon bond-forming reactions.

Key Chemical Reactions and Synthesis:

The most prominent application of 4-Methyl-2-(tributylstannyl)pyridine lies in its utility as a nucleophilic coupling partner in palladium-catalyzed cross-coupling reactions. The Stille coupling, which involves reacting an organotin compound with an organohalide, is a prime example. The tributylstannyl group readily undergoes transmetalation with palladium catalysts, facilitating the formation of new carbon-carbon bonds. This makes it an invaluable intermediate for synthesizing complex organic molecules, including pharmaceuticals and advanced materials. Synthesis typically involves metalation-stannylation reactions of suitably substituted pyridines or cross-coupling strategies.

Physical Properties and Handling:

Typically, 4-Methyl-2-(tributylstannyl)pyridine appears as a liquid. Its solubility profile indicates good compatibility with common organic solvents, while it shows limited solubility in water, consistent with its hydrophobic tributyl groups. Due to the reactive nature of organotin compounds, proper handling and storage are essential. Recommendations often include storage under an inert atmosphere and at refrigerated temperatures to maintain purity and prevent degradation.

Applications in Research and Industry:

The primary use of CAS 301652-23-3 is as a versatile building block in organic synthesis. It is widely employed in academic research and industrial R&D for creating complex heterocyclic structures relevant to medicinal chemistry and material science. Its ability to introduce a functionalized pyridine moiety makes it a sought-after intermediate for drug discovery and the development of novel chemical entities.

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