4-Formylphenylboronic acid CAS:87199-17-5

4-Formylphenylboronic acid (4-FPBA) is a compound renowned for its versatile applications, owing to its distinctive molecular structure comprising a boronic acid moiety attached to a phenyl ring substituted with a formyl group at the para position. 1. Synthetic Chemistry: Suzuki-Miyaura Cross-Coupling: 4-FPBA serves as a key reagent in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of various biaryl compounds. This reaction plays a pivotal role in pharmaceutical synthesis and material science. 2. Functional Group Transformation: Aldehyde Chemistry: The formyl group (-CHO) of 4-FPBA undergoes diverse transformations, including condensation, reduction, and oxidation reactions. This versatility allows for the synthesis of complex molecules with tailored functionalities. 3. Catalysis and Ligand Design: Transition Metal Complexation: 4-FPBA derivatives have been explored as ligands in transition metal catalysis, enhancing catalytic activity and selectivity in organic transformations such as hydrogenation and cross-coupling reactions. Asymmetric Synthesis: Chiral 4-FPBA derivatives have been employed in asymmetric synthesis, enabling the construction of enantioenriched molecules with high stereocontrol. 4. Biomedical Applications: Prodrug Design: 4-FPBA derivatives have been investigated for their potential as prodrugs, where enzymatic cleavage of the boronic ester linkage releases active pharmaceutical agents selectively at target sites, reducing off-target effects. Bioconjugation: The reactivity of the formyl group enables bioconjugation strategies for attaching biomolecules such as peptides, antibodies, and nucleic acids to surfaces or other molecules for diagnostic and therapeutic purposes. In summary, 4-Formylphenylboronic acid is a versatile compound with broad utility in synthetic chemistry, catalysis, and biomedical applications. Its unique reactivity and functional group tolerance make it a valuable building block for the construction of complex molecules and functional materials.