ortho-Bromo benzyl thiol combining a soft nucleophilic –SH and an aryl-bromide handle. It serves as:
A dual-functional linker in Pd-catalysed one-pot thio-arylations, giving benzothiazole or benzothiophene APIs with 85–92 % yield ;
A photolabile protecting group for alcohols/amines—S-benzyl cleavage occurs under 365 nm LED or single-electron oxidant, useful in photoresponsive drug-delivery systems;
A precursor for gold-silver nanoclusters (Au₂₅(SR)₁₈) and SERS-active SAMs, where the ortho-bromine lowers surface defect density by 30 % compared with unsubstituted benzyl thiol;
A building block for macrocyclic diterpenes and mitomycin antibiotics via radical cyclisation routes ;
A chain-transfer agent in RAFT polymerisation, enabling post-polymerisation modification through Suzuki or Sonogashira coupling on the aryl bromide.
Store under nitrogen at 2–8 °C, away from light and oxidants.
