|Jmol-3D images||Image 1|
|Molar mass||218.34 g mol−1|
|Melting point||61 to 62 °C (142 to 144 °F; 334 to 335 K)|
|Solubility in water||Insoluble|
|Solubility in other solvents||Soluble in diethyl ether, benzene, carbon disulfide, and THF|
|Dipole moment||0 D|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Diphenyl disulfide is the chemical compound with the formula (C6H5S)2. This colorless crystalline material is often abbreviated Ph2S2. It is one of the most popular organic disulfides used in organic synthesis. Minor contamination by thiophenol is responsible for the disagreeable odour associated with this compound.
Preparation and structure
Ph2S2 is usually prepared by the oxidation of thiophenol:
- 2 PhSH + I2 → Ph2S2 + 2 HI
Like most organic disulfides, the C2S2 core of Ph2S2 is non-planar with a dihedral angle approaching 85°.
- RC(O)CHLiR’ + Ph2S2 → RC(O)CH(SPh)R’ + LiSPh
Ph2S2 undergoes reduction, a reaction characteristic of disulfides:
- Ph2S2 + 2 M → 2 MSPh (M = Li, Na, K)
Hydride reagents such as sodium borohydride and super hydride can also be used as reductants. The salts PhSM are sources of the potent nucleophile PhS-. Most alkyl halides, RX (X = halide) convert it to the thioethers with the general formula RSPh. Analogously, protonation of MSPh gives thiophenol:
- PhSM + HCl → HSPh + MCl
Catalyst for photoisomerization of alkenes
- Ravikumar,K. S.; Kesavan, V.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. (2003), "Mild and Selective Oxidation of Sulfur Compounds in Trifluoroethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide", Org. Synth. 80: 184
- Byers, J. H. "Diphenyl Disulfide" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289.
- Thalmann, A. Oertle, K.; Gerlach, H. (1990), "Ricinelaidic Acid Lactone", Org. Synth.; Coll. Vol. 7: 470
- Field, L.; Locke, J. M. (1973), "Methyl Benzenesulfinate", Org. Synth.; Coll. Vol. 5: 723