Phenyl vinyl sulfide is the smallest aromatic–vinyl thio-ether, consisting of a phenyl and a vinyl group linked by a sulfur atom. The molecule is air-stable, freely miscible with common organic solvents (dichloromethane, chloroform, ethyl acetate, alcohols, ketones), and essentially insoluble in water. Commercial material is normally supplied with 200 ppm tert-butylcatechol (TBC) as polymerisation inhibitor.
Key physicochemical data:
Density: 1.042 g cm⁻³ (25 °C)
Refractive index n²⁰/D: 1.599
Boiling point: 94–95 °C / 25 mmHg; 204 °C / 760 mmHg
Flash point: 45 °C (114 °F, closed cup)
Log P (octanol/water): 2.9 (predicted)
Typical uses:
Versatile building block for benzo[b]thiophenes, vinyl sulfoxides/sulfones and other sulfur-containing heterocycles via cyclo-addition, cross-coupling or oxidation chemistry .
Precursor for photo-initiators, OLED electron-transport materials and flavour/fragrance intermediates.
Model substrate for mechanistic studies on vinyl C–S bond activation and metal-catalysed coupling reactions.
Quality specification (commercial grade):
Purity (GC): ≥97 % (typically 98 % min.)
Water content (KF): ≤0.2 %
Inhibitor (TBC): 150–250 ppm (when specified)
Residue on ignition: ≤0.1 %
Heavy metals: ≤20 ppm
Hazard statement:
Flammable liquid and vapour (H226). Causes skin and eye irritation (H315 + H319). Keep away from heat, sparks and open flames. Use gloves, goggles and adequate ventilation. Store under nitrogen with polymerisation inhibitor. SDS available on request .
