4-Fluoro-β-nitrostyrene (CAS number 706-08-1) is a fluorinated styrene with a nitro group substituted on the β-carbon. 4-Fluoro-β-nitrostyrene is a typical Michael acceptor with the electron withdrawing nitro group, which is readily for conjugated addition. When the conjugated addition is catalyzed by a chiral ligand, such as l-proline, syn-addition is favored, and the chirality of the Michael adducts can be selectively controlled. Hence, 4-fluoro-β-nitrostyrene has been exploited for chiral γ-nitroaldehydes, a precursor for pharmaceutically active γ-aminobutyric acid (GABA). 4-Fluoro-β-nitrostyrene is also used to synthesize benzopyran(chromenes) derivatives as pharmaceutical active ingredients(APIs).
In antibacterial activity study, 4-fluoro-β-nitrostyrene binds to PTP1B enzymes via hydrogen bonding interaction. It is followed by a Michael addition of thiol groups leading to the inhibition of protein tyrosine phosphatases in the microorganisms.