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

A12586 Diphenyl disulfide, 98%

Codice CAS
882-33-7
Sinonimi
Phenyl disulfide

Dimensioni Prezzo ($) Quantità Disponibilità
50g 37,70
250g 139,00
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Diphenyl disulfide, 98%

MDL
MFCD00003065
EINECS
212-926-4

Proprietà chimiche

Formula
C12H10S2
Peso formula
218.34
Punto di fusione
58-62°
Punto di ebollizione
310°
Solubilità
Insoluble in water.

Applicazioni

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.

Note

Stable under recommended storage conditions. Incompatible with oxidizing agents.

Letteratura

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).

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H315-H319-H335

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

Dichiarazioni precauzionali: 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.

Altri riferimenti

Beilstein
639794
Codice tariffe armonizzato
2930.90
TSCA
Yes
RTECS
SS6825000

Raccomandato

  • A10173

    Trifluoromethanesulfonic acid, 98+%
  • A10221

    Imidazole, 99%
  • A10849

    Benzenesulfonyl chloride, 98%
  • A12197

    6-Mercaptopurine monohydrate, 98%
  • 11186

    Yttrium(III) acetate tetrahydrate, REacton®, 99.99% (REO)

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