4-Phenylthio benzyl chloride is an aromatic sulfide carrying a reactive chloromethyl group para to the sulfur bridge. It is moisture-sensitive, freely soluble in dichloromethane, ethyl acetate and toluene, and essentially insoluble in water. Commercial material is supplied ≥98 % pure and should be stored under inert atmosphere.
Key physicochemical data:
Melting point: 38–40 °C (lit.)
Boiling point: 340 °C / 760 mmHg (predicted)
Density: 1.28 g cm⁻³ (25 °C, solid)
Refractive index n²⁰/D: 1.635 (50 °C)
Flash point: >110 °C (closed cup)
Log P (octanol/water): 4.6 (predicted)
Typical uses:
Versatile electrophile for the introduction of the 4-phenylthio-benzyl (PhSCH₂–Ar) protecting/activating group in alcohols, amines and carboxylic acids.
Key intermediate for sulfur-containing pharmaceutical intermediates, optical brighteners and UV-absorbers.
Precursor for sulfur-stabilised carbanions used in Julia–Kocienski olefinations and related C=C bond-forming reactions.
Quality specification (commercial grade):
Purity (GC): ≥98 %
Water content (KF): ≤0.2 %
Free chloride (as Cl⁻): ≤0.1 %
Residue on ignition: ≤0.1 %
Heavy metals: ≤20 ppm
Hazard statement:
Causes severe skin burns and eye damage (H314). Harmful if swallowed (R22). Reacts violently with water and strong bases. Use only with adequate ventilation, gloves and eye protection; store under argon. SDS available on request.
