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882-33-7 - Diphenyl disulfide, 98% - Phenyl disulfide - A12586 - Alfa Aesar

A12586 Diphenyl disulfide, 98%

Número CAS
882-33-7
Nombre Alternativo
Phenyl disulfide

Tamaño Precio ($) Cantidad Disponibilidad
50g 38,11
250g 122,40
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Diphenyl disulfide, 98%

MDL
MFCD00003065
EINECS
212-926-4

Propiedades químicas

Fórmula
C12H10S2
Peso molecular
218.34
Punto de fusión
58-62°
Punto de ebullición
310°
Solubilidad
Insoluble in water.

Aplicaciones

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.

Notas

Stable under recommended storage conditions. Incompatible with oxidizing agents.

Referencias documentales

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).

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Indicaciones de precaución: P280g-P305+P351+P338

Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Otras referencias

Beilstein
639794
Código de tarifa arancelaria unificado
2930.90
TSCA
Yes
RTECS
SS6825000

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