2,2′,6,6′-Tetrachlorodiphenyl disulfide is an aromatic disulfide in which both phenyl rings are substituted with two chlorine atoms at the ortho positions. The steric bulk and electron-withdrawing character of the four chlorine atoms render the S–S bond markedly resistant to reductive cleavage and impart high thermal stability. The compound is essentially insoluble in water, sparingly soluble in hexane, and readily soluble in dichloromethane, chloroform, hot ethanol and toluene. Commercial lots are released at ≥98 % purity and are stable for ≥2 years when stored in a tightly closed container at 2–8 °C away from light.
Key physicochemical data:
Melting point: 148–150 °C (lit.)
Predicted boiling point: 436 °C / 760 mmHg
Density: 1.62 g cm⁻³ (25 °C, solid)
Flash point: >200 °C
Log P (octanol/water): 6.7 (predicted)
Typical uses:
Sterically hindered building block for redox-robust organic semiconductors and liquid-crystalline materials.
Precursor for thiol-functionalized tetra-ortho-chloro ligands used in asymmetric catalysis.
Model substrate for mechanistic studies on hindered disulfide bond activation and chlorine-directed aromatic functionalization.
Quality specification (commercial grade):
Purity (HPLC): ≥98 %
Water content (KF): ≤0.3 %
Residual solvents (GC): ≤0.5 %
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 reducing agents and light. SDS available on request.
