An ambiphilic aromatic thiol carrying an electron-withdrawing 3-chloro and a 2-fluoro substituent. The vicinal halogens lower the pKa of the –SH group to ≈5.0 and enhance oxidative stability, while the electron-poor ring remains susceptible to nucleophilic aromatic substitution. Key applications include:
Agro-chemical building block: the copper-catalysed S-arylation installs the 3-Cl-2-F-phenyl-sulfur motif into pyrazole carboxanilides, delivering potent SDHI fungicides with improved metabolic stability versus des-halo 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 after 24 h while suppressing tarnishing in saline atmospheres.
Heavy-metal scavenger: the soft sulfur and electron-poor ring form a stable Pd(II) complex (log K = 18.7), 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.
