A bifunctional aromatic thiol combining a 5-chloro substituent with a 2-n-propoxy ether. The strong +M effect of the propoxy group raises the HOMO of sulfur (pKa ≈ 6.2) while the para-chlorine lowers electron density on the ring, giving unique reactivity for:
High-impact savoury flavour building block – at 0.1–0.5 ppm it delivers a roasted meat/onion note with an odour threshold <0.02 ppb, used in soups, baked goods and meat analogues ;
Agro-chemical intermediate – Cu-catalysed thio-arylation affords 2-alkylthio-4-chlorophenols active as rice-blast fungicides;
RAFT chain-transfer agent for living polymerisation of methacrylates; chain-end can be photo-cleaved (365 nm) for block-copolymer synthesis;
SERS-active SAMs on gold – the propoxy tail increases surface hydrophobicity and reduces defect density by 25 %, enhancing mercury-ion detection sensitivity;
Benzothiazole UV-absorbers – cyclisation with aldehydes gives 2-substituted-6-chlorobenzothiazoles with λmax 340 nm.
Store under nitrogen at 2–8 °C, away from light and oxidants.
