2-Bromopyridine (CAS109-04-6)

Uses:

• Pharmaceuticals: Crucial in creating drug molecules, acting as a scaffold for anti-cancer drugs (e.g., Cobimetinib, Vismodegib) and anesthetics (e.g., Remimazolam).
• Agrochemicals: Used in the synthesis of various plant protection agents and pesticides.
• Organic Synthesis: A versatile reagent for creating carbon-nitrogen (C-N) bonds through cross-coupling reactions (like Negishi coupling) and for introducing the 2-pyridyl group.
• Specialty Chemicals: Employed in research and industry for producing other complex organic compounds and intermediates.

• Building Block: Its bromine atom makes it highly reactive, allowing chemists to easily attach other functional groups.
• Organometallic Reagents: Reacts with reagents like butyllithium to form 2-lithiopyridine, a powerful synthetic tool.
• N-Oxidation: Can be converted to its N-oxide, enabling further functionalization, as seen in the synthesis of pyrithione.

Key Applications

• Pharmaceuticals: An essential intermediate for drugs including remimazolam (anesthetic) and cobimetinib, vismodegib (anticancer agents).
• Agrochemicals: Used in the production of various crop protection chemicals.
• Biocides: A precursor for pyrithione-based antifungal and antibacterial agents.
• Organic Synthesis: Acts as a key reagent in:
  • Cross-Coupling Reactions: Forms new carbon-carbon (C-C) and carbon-nitrogen (C-N) bonds via palladium-catalyzed reactions like Suzuki and Negishi couplings.
  • Nucleophilic Substitutions: Reacts to introduce functional groups, like sulfur, after conversion to 2-lithiopyridine or N-oxide.

• Its reactivity at the 2-position makes it ideal for introducing the 2-pyridyl group into larger molecules.
• It is converted into versatile organometallic reagents, such as 2-lithiopyridine, by reaction with butyllithium.

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