PhCH2SSCH2Ph

PhCH2SSCH2Ph, commonly called dibenzyl disulfide, is an organosulfur compound in which two benzyl groups are joined by a disulfide bond (PhCH2-S-S-CH2Ph). Its molecular formula is C14H14S2 and the approximate molecular weight is 246.4 g/mol. The molecule is nonpolar and typically exists as a colorless to pale yellow solid or oil at room temperature; it is sparingly soluble in water and more soluble in many organic solvents such as dichloromethane, benzene, and alcohols.

Synthesis and preparation methods include oxidative coupling of benzyl mercaptan (PhCH2SH) or oxidation of the corresponding thioether, dibenzyl sulfide, to the disulfide. Alternative routes involve oxidation of thiolate intermediates in the presence of mild oxidants. These routes provide access to the symmetric disulfide from common benzyl sulfur precursors.

Reactions and applications: The S-S bond in dibenzyl disulfide can undergo homolytic cleavage under radical conditions to generate benzyl thiyl radicals, enabling various radical transformations. It also participates in thiol-disulfide exchange, allowing formation of mixed disulfides with other thiols and enabling manipulation of sulfur-containing linkages in organic synthesis. As a reagent, it can be used to introduce benzylthio motifs or to serve as a precursor to benzyl thiols upon reduction or exchange, depending on the reaction conditions.

Safety and handling: Dibenzyl disulfide is an irritant and should be handled with appropriate personal protective equipment. It should be stored in a well-closed container away from oxidizers and sources of heat or ignition, under recommended storage conditions.