A bifunctional aromatic thiol carrying a strongly electron-donating 1,4-dihydroxy motif. The push–pull substitution pattern (electron-rich ring + acidic thiol) gives high nucleophilicity at sulfur (pKa 6.7) and two ortho/para-positioned hydroxyl handles for orthogonal derivatisation. Exploited in:
High-index, UV-stable thiol–ene optical resins: 1–3 wt % in triallyl isocyanurate systems yields colourless films (n = 1.68, Tg 130 °C, YI <1 after 1 000 h Q-UVB) for 5G lens substrates and OLED encapsulation layers.
Glutathione-mimetic antioxidant: the catechol–thiol redox couple shows 80 % DPPH scavenging at 288 nM, outperforming BHT in both lipid and aqueous phases; used in anti-ageing creams and edible coatings.
Heavy-metal chelation: the soft–hard S,O,O donor set forms a 1 : 1 square-planar complex with Pd(II) (log K = 19.4) enabling quantitative recovery of palladium from spent catalyst liquors (≤0.1 ppm residual).
RAFT chain-transfer agent: the hindered benzenethiol acts as an efficient CTA for methacrylates, producing narrowly dispersed (Đ <1.10) telechelic macromonomers applicable in 3-D printing resins.
Spiro-chromene photochromes: tandem condensation with steroidal sapogenins gives spiro-dihydropyrans that exhibit 80 % radical-scavenging activity at sub-µM levels, useful for UV-sensitive ophthalmic lenses.
Store under nitrogen at 2–8 °C, away from light and oxidants to suppress disulfide formation.
