- Diphenyl disulfide
Diphenyl disulfide Identifiers CAS number PubChem ChemSpider ChEMBL RTECS number SS6825000 Jmol-3D images Image 1 Properties Molecular formula C12H10S2 Molar mass 218.36 g/mol Appearance Colourless crystals Density ? g/cm3 Melting point
Solubility in water Insoluble Solubility in other solvents Diethyl ether,
Structure Dipole moment 0 D Hazards R-phrases 36/37/38 S-phrases 26 Main hazards Flammable Related compounds Related compounds C6H5SH,
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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°.
Ph2S2 is mainly used in organic synthesis as a source of the PhS substituent. A typical reaction entails the formation of PhS-substituted carbonyl compounds via the enolate:
- 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
Ph2S2 reacts with chlorine to give phenylsulfenyl chloride PhSCl (Zincke disulfide cleavage). This species is somewhat difficult to isolate, so it is usually generated in situ.
Catalyst for photoisomerisation 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, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v80p0184
- ^ 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., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv7p0470 ; Coll. Vol. 7: 470
- ^ Field, L.; Locke, J. M. (1973), "Methyl Benzenesulfinate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0723 ; Coll. Vol. 5: 723
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