Para-fluoro benzyl thiol combining a soft nucleophilic –SH and an aryl-fluoride handle. The electron-withdrawing fluorine lowers sulfur pKa (~9.5) and accelerates thiol-ene or SNAr reactions, enabling:
S-protecting group for alcohols/amines in peptide and nucleoside synthesis, removable by mild oxidation or photolysis;
Precursor to bis(4-fluorobenzyl) di- and tetra-sulfides used as degradation markers for fluorapacin antibiotics ;
Building block for Au₂₅(SR)₁₈ nanoclusters and SERS-active SAMs on gold, where the para-F reduces surface defect density by 20 % ;
Agro-chemical intermediate via Cu-catalysed thio-arylation to give 4-fluoro-aryl sulfide fungicides;
Chain-transfer agent in RAFT polymerisation, allowing post-polymerisation functionalisation through Suzuki or SNAr chemistry on the aryl fluoride.
Store under nitrogen at 2–8 °C, away from light and oxidants.
