An ambiphilic aromatic thiol that combines an electron-withdrawing para-chlorine with an ortho-methyl group, delivering high nucleophilicity (pKa 6.2) and good lipophilicity (clogP 3.4). The dual substituent pattern is exploited in:
Agro-chemical leads: the copper-catalysed S-arylation installs the 5-Cl-2-Me-phenyl-sulfur fragment into pyrazole carboxanilides, delivering potent SDHI fungicides with improved metabolic stability versus des-chloro analogues.
High-κ optical coatings: thiol–ene photopolymerisation with triallyl isocyanurate yields colourless films (n 1.64, Tg 125 °C, YI <1 after 500 h Q-UVB) for OLED barrier layers.
Silver-antimicrobial SAMs: self-assembled monolayers on Ag(111) give densely packed hydrophobic surfaces (water contact angle 102°) that sustain >99 % bacterial kill rates after 24 h while suppressing tarnishing in saline atmospheres.
Heavy-metal scavenger: the soft sulfur and π-electron-withdrawing chlorine form a bidentate S,Cl-binding pocket that selectively extracts Hg²⁺ (log K = 16.8) from acidic industrial brines, enabling resin-based columns that reduce mercury to <0.3 ppb.
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.
Store under nitrogen at 2–8 °C, away from light and oxidants to prevent disulfide formation.
