S-Phenyl benzenesulfonothioate is a mixed thiosulfonic ester (ArSO₂–SAr) combining a benzenesulfonyl and a phenylthio unit. The compound is essentially odourless, stable to air and moisture, and readily soluble in dichloromethane, chloroform, ethyl acetate and acetone, while only sparingly soluble in water (<50 mg L⁻¹ at 25 °C). It serves as a mild, crystalline source of the “PhS” or “PhSO₂” synthon and is employed for the chemoselective transfer of either moiety under neutral or mildly basic conditions. Commercial material is supplied at ≥98 % purity and should be stored at 2–8 °C to preserve colour and assay.
Key Physicochemical Data:
Melting point: 45 °C (lit.)
Boiling point: 125 °C / 0.01 mmHg (lit.)
Density: 1.4 ± 0.1 g cm⁻³ (20 °C, solid)
Flash point: 200.7 ± 24 °C (closed cup)
Log P (octanol/water): 3.76 (predicted)
Refractive index: 1.663 (20 °C, solid)
Typical Uses:
Chemoselective sulfenylation or sulfonylation reagent for the preparation of unsymmetrical sulfides, sulfoxides and sulfones from Grignard or organozinc reagents.
Precursor to unsymmetrical di-aryl disulfides via metal-catalysed cross-coupling with aryl halides.
Building block for thiosulfonate-based pro-fragrances and anti-oxidant additives in personal-care formulations.
Quality Specification (Commercial Grade):
Purity (HPLC): ≥98 %
Water content (KF): ≤0.3 %
Free acid (as PhSO₃H): ≤0.2 %
Residue on ignition: ≤0.1 %
Heavy metals: ≤20 ppm
Hazard Statement:
Causes skin and eye irritation (H315 + H319). May cause respiratory irritation if inhaled. Avoid dust formation; use gloves, goggles and adequate ventilation. Store in a cool, dry place away from strong oxidants and bases. SDS available on request.
