An electron-rich aromatic thiol carrying two adjacent methyl donors at the 2- and 3-positions, affording high nucleophilicity (pKa 6.5) and excellent lipophilicity (clogP 3.3). The steric shield provided by the vicinal methyl groups raises the oxidation potential, making the compound a preferred building block for:
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 coatings: self-assembled monolayers on Ag(110) give densely packed hydrophobic surfaces (water contact angle 103°) 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 .
Heavy-metal scavenger: the soft sulfur and adjacent 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 .
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.
