![[(Chloromethyl)thio]benzene](/upload/20251022/7e60ff41073210d3f0e1fb2d85ced3a6.png)
[(Chloromethyl)thio]benzene is an aromatic sulfide carrying a reactive chloromethyl group attached to sulfur. It is moisture-sensitive, freely miscible with common organic solvents (dichloromethane, ethyl acetate, toluene) and essentially insoluble in water. Commercial material is supplied ≥98 % pure and should be stored under inert atmosphere.
Key physicochemical data:
Density: 1.23 g cm⁻³ (25 °C)
Refractive index n²⁰/D: 1.585
Boiling point: 220 °C / 760 mmHg (predicted)
Flash point: 96 °C (closed cup)
Log P (octanol/water): 2.8 (predicted)
Typical uses:
Versatile electrophile for the introduction of the phenylthiomethyl (PhSCH₂–) protecting/activating group in alcohols, amines and carboxylic acids.
Key intermediate for benzyl-type sulfides, sulfoxides and sulfones used in pharmaceutical and agro-chemical synthesis.
Precursor for sulfur-stabilised carbanions (PhSCH₂⁻) 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.
