PhSSPh

PhSSPh, commonly known as diphenyl disulfide, is an organosulfur compound with the formula C12H10S2. Its structure consists of two phenyl rings linked by a disulfide bond (Ph-S-S-Ph). It is a widely used reagent and building block in organic synthesis and materials science.

In its appearance, PhSSPh is typically a pale yellow solid that is soluble in many nonpolar organic solvents and only sparingly soluble in water. It is relatively stable under ambient conditions but can decompose at elevated temperatures or in strongly reducing or oxidizing environments.

Production and sources: Diphenyl disulfide is commonly prepared by oxidative coupling of thiophenol or diarylthiolates, using oxidants such as air, iodine, or other reagents. It can also be formed via other oxidative coupling methods that join two phenylthio units.

Reactions and applications: PhSSPh serves as a source of phenylthiyl radicals under photochemical or thermal conditions, enabling various thiolation and thioaryl-transfer reactions. It can participate in disulfide exchange and can be reduced to two equivalents of thiophenol. In polymer and materials chemistry, diphenyl disulfide acts as a redox-responsive disulfide linker. In organic synthesis, it is used to introduce phenylthio groups into substrates or as a coupling partner in methods that form C–S bonds or thioaryl motifs.

Safety and handling: Diphenyl disulfide can irritate skin and eyes and has a sulfurous odor. It should be handled in a well-ventilated area, away from strong oxidizers, acids, and bases, and stored in a cool, dry place.