A sterically hindered, electron-rich aromatic thiol in which two ortho-methyl groups block the thiol site and raise its oxidation potential. The high electron density (pKa 6.5) and lipophilic clogP 3.3 make it a preferred building block for:
High-performance RAFT chain-transfer agent: the hindered thiol yields narrowly dispersed (Đ <1.10) polystyrene and polymethacrylate macro-CTAs for block-copolymer lithography and 3-D printing resins .
Silver-antimicrobial SAMs: self-assembled monolayers on Ag(110) give densely packed hydrophobic surfaces (water contact angle 102°) that retain >99 % bacterial kill after 24 h while suppressing tarnishing in saline atmospheres .
FEMA GRAS flavour ingredient: the thiol and its oxidised disulfide impart roast-beef, coffee and nut nuances at thresholds down to 0.02 ng L⁻¹; used in meat, beverage and confectionery aromatisation at 0.05–5 ppm [^156^, ^163^].
Heavy-metal scavenger: the soft sulfur and electron-rich ring form a stable Pd(II) complex (log K = 18.3), enabling recovery of palladium from spent cross-coupling liquors to <0.2 ppm residual .
Synthetic relay to benzothiazoles: metal-free oxidative cyclisation with aldehydes furnishes 2-substituted benzothiazoles in 88–94 % yield, streamlining pharmaceutical building-block synthesis .
Store under nitrogen at 2–8 °C, away from light and oxidants to prevent disulfide formation .
