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Diphenyl disulfide is one of the most popular organic disulfides used in organic synthesis. It is used as a reagent for the α-phenylsulfenylation of carbonyl compounds. It participates in hydrothiolation of alkynes via amine-mediated single electron transfer mechanism. It is the hydrolysis product of dyfonate.
Tsuyoshi Taniguchi; Tatsuya Fujii; Atsushi Idota; Hiroyuki Ishibashi. Reductive addition of the benzenethiyl radical to alkynes by amine-mediated single electron transfer reaction to diphenyl disulfide. Organic Letters. 2009, 11, (15)3298-3301
S.C.Mitchell; R.M.Nickson; E.R.Porter; W.F.Jackson; S.L.Preston; A.Q.Zhang. The fate of diphenyl sulphide, diphenyl sulphoxide and diphenyl sulphone in the rat. Drug Metabolism and Drug Interactions. 2000, 16, (3)191-206
Sulfenylation agent for enolates of ketones, esters or carboxylic acid dianions: J. Am. Chem. Soc., 95, 6840 (1973); 98, 4887 (1976); Chem. Rev., 78, 363 (1978). Oxidation to the sulfoxide and thermal elimination can be used for the conversion of ketones to enones via thermal sulfoxide elimination, less frequently used than the selenoxide route (cf preceding entry), due to the higher temperatures required.
Also sulfenylates organolithium reagents from, e.g. lithiated furans: J. Org. Chem., 46, 2473 (1981).
Alkyl halides under phase-transfer conditions give alkyl phenyl sulfides in good yields,: Synth. Commun., 12, 595 (1982), and alkenyl halides in the presence of CuI give alkenyl sulfides: Chem. Lett., 769 (1989).
For use as a catalyst in the photochemical cis-trans isomerization of olefins (used in the synthesis of the macrolide ricinelaidic acid lactone), see: Org. Synth. Coll., 7, 470 (1990).
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant