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Divinyl sulfide

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Divinyl sulfide
Names
Preferred IUPAC name (Ethenylsulfanyl)ethene
Other names vinyl sulfide, DVS
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H6S/c1-3-5-4-2/h3-4H,1-2H2Key: UIYCHXAGWOYNNA-UHFFFAOYSA-N
SMILES
  • C=CSC=C
Properties
Chemical formula C4H6S
Molar mass 86.15 g·mol
Appearance colorless liquid
Density 0.9098 g/cm (20 °C)
Melting point 20 °C (68 °F; 293 K)
Boiling point 84 °C (183 °F; 357 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Divinyl sulfide is the organosulfur compound with the formula S(CH=CH2)2. A colorless liquid with a faint odor, it is found in some species of Allium.

Preparation

Divinyl sulfide is formed from hydrogen sulfide and acetylene. Divinylsulfide can arise when inadvertently when acetylene is generated by hydrolysis of technical-grade calcium carbide contaminated with calcium sulfide.

Divinylsulfide was first prepared in 1920 by the reaction of bis(2-chloroethyl)sulfide with sodium ethoxide:

(ClCH2CH2)2S + 2 NaOEt → (CH2=CH)2S + 2 EtOH + 2 NaCl

Monovinyl sulfides

With the formula CH2=CHSR, a variety of monovinyl sulfides are known. They can arise by the dehydrohalogenation of -2-haloethyl phenyl sulfides. One example is phenyl vinyl sulfide. Alkyl ketones react with thiols in the presence of phosphorus pentoxide to give vinyl sulfides:

RSH + CH3C(O)R' → CH2=C(SR)R' + H2O

References

  1. "Divinyl sulfide (FDB012121)". FooDB.
  2. Trotuş, Ioan-Teodor; Zimmermann, Tobias; Schüth, Ferdi (2014). "Catalytic Reactions of Acetylene: A Feedstock for the Chemical Industry Revisited". Chemical Reviews. 114 (3): 1761–1782. doi:10.1021/cr400357r. PMID 24228942.
  3. ^ Boris A. Trofimov; S. V. Amosova (1984). "Divinyl Sulfide: Synthesis, Properties, and Applications". Sulfur Reports. 3 (9): 323–393. doi:10.1080/01961778408082463.
  4. Nina A. Nedolya; Boris A. Trofimov (1994). "Sulfur-Containing Vinyl Ethers". Sulfur Reports. 15 (2): 237–316. doi:10.1080/01961779408048961.
  5. Leo A. Paquette; Richard V. C. Carr (1986). "Phenyl Vinyl Sulfone and Sulfoxide". Organic Syntheses. 64: 157. doi:10.15227/orgsyn.064.0157.
  6. Daniel S. Reno; Richard J. Pariza (1997). "Phenyl Vinyl Sulfide". Organic Syntheses. 74: 124. doi:10.15227/orgsyn.074.0124.
  7. Trost, Barry M.; Lavoie, Alvin C. (1983). "Enol thioethers as enol substitutes. An alkylation sequence". Journal of the American Chemical Society. 105 (15): 5075–5090. doi:10.1021/ja00353a037.
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