A bifunctional aromatic building block that couples a nucleophilic thiol and a primary alcohol on a para-substituted benzene ring. The two orthogonal handles enable sequential or one-pot chemoselective transformations, making the molecule a strategic intermediate for:
Self-assembled monolayers (SAMs) on gold: the thiol anchors the surface while the alcohol provides a hydroxyl-terminated interface (water contact angle 28°) for bioconjugation or further esterification, yielding low-fouling biosensor chips .
X-ray-opaque dental resins: thiol–ene photopolymerisation with triallyl isocyanurate gives highly cross-linked networks (ρ 1.45 g cm⁻³) that exhibit 30 % higher radiopacity than commercial Bis-GMA resins, facilitating post-operative radiographic diagnosis.
Redox-sensitive pro-fragrances: enzymatic oxidation with laccase generates the corresponding disulfide, a long-lasting musk-like odorant (odour threshold 0.03 ng L⁻¹) used in fine perfumery.
Metal-free aerobic oxidation: in the presence of bis(methoxypropyl) ether the –CH₂OH group is selectively oxidised to 4-mercaptobenzoic acid (84 % yield) under ambient O₂, providing an eco-friendly route to thiophenolic acids .
RAFT chain-transfer agent: the hindered benzylic thiol acts as an efficient CTA for methacrylates, producing narrowly dispersed (Đ <1.10) telechelic macromonomers applicable in 3-D printing resins.
Store under nitrogen at 2–8 °C, protected from light and peroxides to suppress disulfide formation .
