A sterically shielded, electron-rich aromatic thiol in which two methyl donors at the 3- and 5-positions raise the –SH electron density (pKa 6.5) while maintaining good oxidative stability. The meta-dimethyl pattern delivers unique reactivity and surface-assembly behaviour, enabling:
High-performance RAFT chain-transfer agent: the hindered thiol produces narrowly dispersed (Đ <1.10) polystyrene and polymethacrylate macro-CTAs for block-copolymer lithography and 3-D printing resins.
Silver-antimicrobial self-assembled monolayers: the densely packed hydrophobic surface (water contact angle 102°) sustains >99 % bacterial kill after 24 h and suppresses Ag tarnishing in saline atmospheres .
Heavy-metal scavenger: the soft sulfur and π-electron-rich ring form a stable complex with Pd(II) (log K = 18.3), enabling recovery of palladium from spent cross-coupling liquors to <0.2 ppm residual .
Flavour & fragrance precursor: laccase-mediated oxidation converts the thiol into the corresponding disulfide, a long-lasting vanilla-like odorant (odour threshold 0.02 ng L⁻¹) used in beverage aromatisation .
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 .
