4-Bromo-2,6-difluoroaniline (CAS 67567-26-4) is a critical intermediate in modern organic synthesis, prized for its unique combination of functional groups and their strategic placement. Its utility spans across pharmaceuticals, agrochemicals, and materials science, largely due to its versatility in coupling reactions and the electronic influence of its fluorine substituents. Understanding its synthesis and reactivity is key for chemists aiming to leverage its full potential. As a premier supplier, we provide high-purity 4-Bromo-2,6-difluoroaniline, enabling complex chemical transformations for innovative applications.

Synthesis Routes for 4-Bromo-2,6-difluoroaniline

The production of 4-Bromo-2,6-difluoroaniline typically involves the targeted bromination of 2,6-difluoroaniline. A common and effective method is the electrophilic aromatic substitution where bromine is introduced at the para position relative to the amine group. This process is often carried out in an acidic medium, such as glacial acetic acid, which can also serve as a solvent. Bromine is added slowly to the solution, and the reaction proceeds efficiently at room temperature over a short period. The yield is typically high, often exceeding 90%, especially under optimized conditions. The work-up involves neutralization, extraction, and purification to yield the desired product.

Alternative methods might involve variations in solvents, catalysts, or reaction conditions to optimize yield, purity, or to adapt to specific manufacturing scales. For instance, using different solvent systems like acetonitrile or dichloromethane can influence reaction rates and selectivity, although acetic acid often provides superior results due to its ability to stabilize reaction intermediates.

Key Reactivity and Applications

The true value of 4-Bromo-2,6-difluoroaniline lies in its rich reactivity, driven by the interplay of its substituents:

  • Bromine for Cross-Coupling: The para-bromine atom is an excellent leaving group for palladium-catalyzed cross-coupling reactions. This includes:
    • Suzuki-Miyaura Coupling: Reacting with boronic acids to form new C-C bonds, crucial for synthesizing biaryl compounds, which are common in pharmaceuticals and advanced materials for OLEDs.
    • Sonogashira Coupling: Reacting with terminal alkynes to create acetylene-bridged systems, important for conjugated polymers and electronic materials.
    • Heck Reaction: Coupling with alkenes to introduce vinyl groups.
  • Amine Group Functionality: The amine group can participate in various reactions, including acylation, alkylation, and diazotization followed by azo coupling for dye synthesis. It also serves as a nucleophile in reactions like the Buchwald-Hartwig amination.
  • Influence of Fluorine Atoms: The two ortho-fluorine atoms have a significant impact on the molecule's electronic properties. They are electron-withdrawing, which can influence the reactivity of the aromatic ring and the amine group. Crucially, they modulate the HOMO-LUMO energy levels of derived conjugated systems, making them suitable for applications in organic electronics such as OLEDs and solar cells, by enhancing charge transport and stability.

These reactivity patterns make 4-Bromo-2,6-difluoroaniline an indispensable intermediate. Its use in synthesizing hole-transporting materials for OLEDs, precursors for novel pharmaceuticals targeting cancer, and components for advanced agrochemicals underscores its importance. If you are looking to buy 4-Bromo-2,6-difluoroaniline, sourcing from a reliable manufacturer like us ensures you receive a high-purity product (≥99.0%) ready for your complex synthesis needs. We are your trusted partner for advancing chemical innovation. Contact us for quotations and sample requests.