A dual-donor aromatic thiol bearing an electron-releasing para-methoxy and an ortho-methyl group, delivering high nucleophilicity (pKa 6.4) and excellent steric-access balance. Applications include:
Late-stage hetero-aryl coupling: the copper(I) thiolate cleanly cross-couples with unactivated bromo-pyrazines under Buchwald conditions, installing metabolically robust 4-MeO-2-Me-phenyl-sulfur fragments into agrochemical leads and JAK-1 inhibitors.
High-κ optical coatings: thiol–ene photopolymerisation with triallyl isocyanurate gives colourless films (n 1.64, Tg 135 °C, YI <1 after 500 h Q-UVB) for AR layers on OLED encapsulation glass.
Mercury-ion optrodes: the soft sulfur and adjacent methoxy oxygen form a bidentate pocket that selectively binds Hg²⁺ (log K 15.3), enabling fibre-optic sensors with a 0.5 ppb detection limit in drinking water.
Fragrance precursor: enzymatic oxidation with chloroperoxidase generates the corresponding disulfide, a long-lasting clove-like odorant (odour threshold 0.02 ng L⁻¹) used in fine perfumery.
RAFT chain-transfer agent: the hindered phenol moiety acts as an internal radical sink, producing narrowly dispersed (Đ <1.10) methacrylic macromonomers for 3-D printing resins.
Store under nitrogen at 2–8 °C, protected from light and peroxides to avoid disulfide formation .
