For any chemist engaged in advanced organic synthesis, a thorough understanding of the chemical properties of their building blocks is fundamental. 5-Bromo-8-fluoroisoquinoline, identified by its CAS number 679433-94-4, is a fascinating molecule that offers significant utility due to its specific structural features. As a key intermediate, its reactivity profile dictates the types of transformations it can undergo and the complexity of molecules that can be built from it. Companies looking to buy this compound for their synthesis projects should consider these chemical aspects.

Molecular Structure and Significance

The chemical formula for 5-Bromo-8-fluoroisoquinoline is C9H5BrFN, with a molecular weight of approximately 226.05 g/mol. The core structure is isoquinoline, a bicyclic aromatic heterocycle containing a nitrogen atom. The strategic placement of substituents is what makes this molecule particularly valuable:

  • Isoquinoline Core: This fused ring system provides a rigid framework common in many biologically active molecules and natural products. The nitrogen atom in the ring can influence solubility and participate in hydrogen bonding or salt formation.
  • Bromine at C5: The bromine atom is an excellent leaving group and a prime site for palladium-catalyzed cross-coupling reactions. This functionality allows for the introduction of carbon-carbon or carbon-heteroatom bonds, which are crucial for elaborating complex molecular structures. For instance, Suzuki, Sonogashira, or Heck reactions can be readily performed at this position.
  • Fluorine at C8: Fluorine is a highly electronegative atom that can significantly alter the electronic properties of the aromatic system. It can influence the molecule's acidity/basicity, lipophilicity, and its interactions with biological targets. The C-F bond is also very strong, generally enhancing metabolic stability in drug molecules.

Reactivity and Synthetic Applications

The interplay of these functional groups provides synthetic chemists with a powerful tool. The bromine atom's reactivity in cross-coupling is complemented by the electronic influence of the fluorine atom and the inherent properties of the isoquinoline ring. Common synthetic strategies employing 5-Bromo-8-fluoroisoquinoline include:

  • Preparation of Arylated Isoquinolines: Using Suzuki coupling with aryl boronic acids to introduce various aromatic substituents at the C5 position.
  • Alkynylation: Employing Sonogashira coupling with terminal alkynes to append carbon chains or functional groups.
  • Amination Reactions: Utilizing Buchwald-Hartwig amination to form carbon-nitrogen bonds, introducing amine functionalities.

When sourcing this chemical, understanding its behavior under various reaction conditions is key. Manufacturers often provide detailed specifications and safety data sheets (SDS) that can guide its proper handling and use in synthesis. If you are looking to buy 5-Bromo-8-fluoroisoquinoline, engaging with suppliers who can provide technical insights into its reactivity will ensure successful project execution.

Conclusion

5-Bromo-8-fluoroisoquinoline is more than just a chemical compound; it is an enabler of molecular innovation. Its well-defined chemical properties, particularly the reactive bromine and the electron-withdrawing fluorine on the robust isoquinoline scaffold, make it an indispensable intermediate for creating novel compounds in pharmaceuticals, agrochemicals, and materials science. For those in need of this versatile building block, securing a reliable supply from a trusted manufacturer is the first step towards unlocking new synthetic possibilities.