3-Bromo-5-fluorobenzaldehyde (CAS 188813-02-7) is a highly valued intermediate in organic chemistry due to its multifaceted reactivity, stemming from the strategic placement of its aldehyde, bromine, and fluorine substituents. For researchers and procurement managers looking to buy this compound, understanding its chemical behavior is key to unlocking its full potential in various synthetic endeavors, from drug development to materials science.

Understanding the Functional Groups and Their Influence
At its core, 3-Bromo-5-fluorobenzaldehyde is a benzaldehyde derivative. The aldehyde group (-CHO) is electron-withdrawing and susceptible to nucleophilic addition and condensation reactions. The bromine atom, a good leaving group, is ideal for palladium-catalyzed cross-coupling reactions. The fluorine atom, with its high electronegativity, also influences the electronic distribution of the aromatic ring, potentially enhancing reactivity or altering regioselectivity in certain transformations.

Key Reactions and Applications:

  • Cross-Coupling Reactions (Suzuki-Miyaura, Heck, Sonogashira): The bromine atom at the 3-position serves as an excellent site for palladium-catalyzed cross-coupling. This allows for the facile introduction of various aryl, vinyl, or alkynyl groups, enabling the construction of complex carbon skeletons. For instance, Suzuki-Miyaura coupling with boronic acids is a common method to synthesize biaryl compounds, which are prevalent in pharmaceutical structures. When you need to buy custom ligands or functionalized aromatic systems, this reaction is invaluable.
  • Nucleophilic Additions to the Aldehyde: The aldehyde group readily undergoes nucleophilic attack. This includes Grignard reactions or organolithium additions to form secondary alcohols, reduction to primary alcohols (using agents like NaBH₄), or oxidation to carboxylic acids. These transformations are fundamental for modifying the aldehyde functionality into other useful groups.
  • Condensation Reactions: The aldehyde group is highly reactive in condensation reactions, such as Schiff base formation with amines, Wittig reactions with phosphonium ylides to form alkenes, and aldol condensations. These reactions are critical for building heterocyclic rings or extending carbon chains, commonly employed in the synthesis of pharmaceuticals and agrochemicals.
  • Nucleophilic Aromatic Substitution (SNAr): While less common for bromine itself, the electron-withdrawing nature of the aldehyde and fluorine groups can activate positions on the ring for SNAr, though the bromine atom is typically the primary target for catalytic transformations.

As a Pharmaceutical Intermediate:
3-Bromo-5-fluorobenzaldehyde is a sought-after precursor in medicinal chemistry. Its structure is frequently incorporated into drug candidates targeting kinases, central nervous system disorders, and infectious diseases. For example, condensing it with specific amines can lead to Schiff bases that are intermediates for potent antifungal agents. Furthermore, its utility in creating complex fluorinated structures makes it relevant for developing PET tracers or compounds with enhanced metabolic stability. Researchers often buy this intermediate to rapidly assemble diverse compound libraries for drug screening.

Manufacturers and Availability:
Reliable manufacturers and suppliers, often based in China, offer 3-Bromo-5-fluorobenzaldehyde with high purity (≥98%). When considering a purchase, inquire about its reactivity profile and ensure the supplier can provide relevant technical data to support its use in your specific reaction conditions. Understanding these reactivity facets ensures that when you buy this compound, you are equipped to effectively utilize its synthetic potential.