A sterically hindered aromatic thiol carrying an electron-donating isopropyl ortho to the –SH group. The bulky substituent raises the oxidation potential and confers high chain-transfer efficiency, while the lipophilic side-chain boosts solubility in non-polar media. Key applications include:
High-performance RAFT chain-transfer agent: the ortho-isopropyl group hinders radical recombination, yielding narrowly dispersed (Đ <1.10) polystyrene and polymethacrylate macro-CTAs for block-copolymer lithography and 3-D printing resins.
Silver-antimicrobial coatings: self-assembled monolayers on Ag(110) give densely packed hydrophobic surfaces (water contact angle 105°) that sustain >99 % bacterial kill rates after 24 h while suppressing tarnishing in saline atmospheres .
Fruity flavour precursor: laccase-mediated oxidation converts the thiol into the corresponding disulfide, a long-lasting grapefruit-like odorant (odour threshold 0.02 ng L⁻¹) used in beverage aromatisation .
Copper-selective flotation collector: the hindered thiolate exhibits 95 % selectivity for Cu²⁺ over Fe³⁺ at pH 9, enabling greener recovery of chalcopyrite from low-grade ores without xanthate collectors .
Synthetic relay to benzothiazoles: one-pot oxidative cyclisation with aldehydes furnishes 2-substituted benzothiazoles in 88–94 % yield under metal-free conditions, streamlining pharmaceutical building-block synthesis .
Store under nitrogen at 2–8 °C, away from light and oxidants to prevent disulfide formation.
