An electron-deficient aromatic thiol in which two adjacent fluorine atoms withdraw electron density and lower the pKa of the –SH group to ≈ 5.8. The ortho-fluoro substituent imparts high oxidative stability and unique reactivity toward nucleophilic aromatic substitution, making the molecule a strategic building block for:
High-index thiol–ene optical resins: photopolymerisation with triallyl isocyanurate yields colourless films (n = 1.60, Tg 125 °C, YI <1 after 500 h Q-UVB) for 5G lens substrates and OLED encapsulation layers.
Silver-antimicrobial self-assembled monolayers: the densely packed fluorinated surface (water contact angle 98°) sustains >99 % bacterial kill after 24 h and suppresses Ag tarnishing in saline atmospheres.
Palladium-selective scavenger: the soft sulfur and electron-poor ring form a stable Pd(II) complex (log K = 18.7), enabling recovery of Pd from spent cross-coupling liquors to <0.1 ppm residual.
Electrophilic thiolation reagent: the pre-activated ArS⁻ species transfers cleanly to electron-rich arenes under oxidative conditions, furnishing unsymmetrical diaryl sulfides for OLED host materials.
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.
