2,2'-Dinitro diphenyl disulfide is an electron-deficient aromatic disulfide in which nitro groups are located ortho to the –S–S– bridge on both benzene rings. The compound is essentially odourless, stable under ambient conditions, freely soluble in hot ethanol, benzene and dichloromethane, and practically insoluble in water.
Key physicochemical data:
Melting point: 194–197 °C (lit. ≥193 °C)
Predicted boiling point: 441.9 °C at 760 mmHg
Density: 1.62 g cm⁻³ (20 °C, solid)
Refractive index: 1.651
Flash point: 221 °C
Log P (octanol/water): 5.35 (predicted)
PSA: 142.2 Ų
Typical uses:
Mild oxidant and “ArS•” radical precursor for photo- and redox-initiated transformations; the ortho-nitro groups facilitate visible-light absorption and single-electron transfer.
Reagent for regioselective o-nitro-phenylthiation of carbonyls, amines and aryl halides; precursor for o-nitro-thiophenols used in metal-catalysed coupling sequences.
Building block for o-nitro-diaryl sulfoxides/sulfones, OLED electron-transport materials and high-purity pharmaceutical intermediates.
Quality specification (commercial grade):
Purity (HPLC): ≥98 % (typically ≥99 %)
Water content (KF): ≤0.3 %
Free thiol (as o-NO₂-PhSH): ≤0.2 %
Residue on ignition: ≤0.1 %
Heavy metals: ≤20 ppm
Hazard statement:
Causes skin and eye irritation (H315 + H319). May cause respiratory irritation (H335). Avoid inhalation of dust; use gloves, goggles and adequate ventilation. Store in a cool, dry place away from oxidants and reducing agents. SDS available on request.
