![1-[(o-Chlorophenyl)thio]-2-propanone](/upload/20251021/56cc8aca0a922b80097197b879544192.png)
An ambiphilic building block that unites a nucleophilic 2-chlorophenyl-thio ether with a ketone handle. The α-thio-ketone motif is readily elaborated via:
Julia–Kocienski olefination: the derived sulfone is shelf-stable and delivers >90 % (E)-selectivity in one-pot Julia couplings to construct fluorinated stilbenes and agrochemical intermediates.
Enolate chemistry: LDA deprotonation gives the α-thio-enolate, which undergoes diastereoselective aldol or Mannich reactions to furnish β-hydroxy- or β-amino-ketones for pharmaceutical synthesis.
High-flux RAFT chain-transfer agent: the sterically hindered tertiary thio-ether yields narrowly dispersed (Đ <1.10) poly(meth)acrylate macro-CTAs for block-copolymer lithography and 3-D printing resins.
FEMA-GRAS meat-flavour precursor: enzymatic oxidation generates the corresponding disulfide, a roast-beef, onion-like odorant (threshold 0.03 ng L⁻¹) used in savoury seasonings at 0.1–5 ppm.
Heavy-metal scavenger: the soft thio-ether sulfur forms a stable 1 : 1 complex with Pd(II) (log K = 17.8), enabling recovery of palladium from spent cross-coupling liquors to <0.2 ppm residual.
Store under nitrogen at 2–8 °C, away from light and oxidants to suppress disulfide formation .
