Organic chemists constantly seek reliable building blocks that offer predictable reactivity and versatility for constructing complex molecular architectures. 3-Bromo-2-methylpyridine (CAS: 38749-79-0) is precisely such a compound, widely employed in both academic research and industrial applications. This guide highlights its chemical properties and practical applications for chemists aiming to master their synthetic endeavors.

Understanding the Reactivity Profile

3-Bromo-2-methylpyridine, also known as 3-Bromo-2-picoline, is characterized by its pyridine core, a methyl substituent at the C2 position, and a bromine atom at the C3 position. This specific arrangement dictates its chemical behavior:

  • Aryl Halide Nature: The bromine atom attached to the aromatic pyridine ring makes it an aryl halide, susceptible to a range of substitution and coupling reactions.
  • Pyridine Nitrogen: The presence of the nitrogen atom imparts basicity and can influence reaction conditions and regioselectivity.
  • Methyl Group: The methyl group can also participate in certain reactions under specific conditions, though its primary role is often steric or electronic influence.

Key Synthetic Transformations Employing 3-Bromo-2-methylpyridine

The utility of 3-Bromo-2-methylpyridine in organic synthesis is vast. Chemists frequently employ it in:

  • Palladium-Catalyzed Cross-Coupling Reactions: This is arguably the most significant application. Reactions like the Suzuki-Miyaura coupling (with boronic acids), Heck reaction (with alkenes), Sonogashira coupling (with alkynes), and Stille coupling (with organostannanes) are efficiently performed using this intermediate. These reactions are crucial for forming new carbon-carbon bonds, a cornerstone of organic synthesis.
  • Nucleophilic Aromatic Substitution (SNAr): While less common for aryl bromides compared to chlorides or fluorides, SNAr reactions can be achieved under forcing conditions or with specific activating groups.
  • Metal-Halogen Exchange: Treatment with strong organometallic bases (like n-butyllithium) can lead to the formation of an organolithium species, which can then react with various electrophiles.
  • Directed Ortho-Metallation (DoM): The pyridine nitrogen can sometimes direct metallation to adjacent positions, though the existing substituents may influence this.

Procuring High-Quality 3-Bromo-2-methylpyridine

For chemists, access to pure and reliable 3-Bromo-2-methylpyridine is essential for successful experimental outcomes. When selecting a supplier, chemists should prioritize suppliers that provide:

  • Detailed Specifications: CAS number (38749-79-0), Molecular Formula (C6H6BrN), Molecular Weight (172.02), and purity (≥99.0% GC).
  • Reputable Manufacturers: Companies with established reputations for quality and consistency in chemical production.
  • Appropriate Packaging: Suitable for laboratory use, ensuring stability and ease of handling.

Purchasing from trusted manufacturers, especially those offering direct sales or robust distribution networks, ensures you receive a product that meets your stringent research needs. For bulk purchases, inquiry regarding pricing and availability from leading chemical suppliers is recommended.

Conclusion

3-Bromo-2-methylpyridine (CAS: 38749-79-0) is an invaluable tool in the organic chemist's toolkit. Its predictable reactivity, especially in cross-coupling reactions, makes it a go-to intermediate for building complex molecules. By understanding its chemistry and ensuring a reliable supply of high-purity material, chemists can confidently accelerate their synthetic projects and drive innovation in their respective fields.