Divinyl sulfide

Source: Wikipedia, the free encyclopedia.
Divinyl sulfide
Names
Preferred IUPAC name
(Ethenylsulfanyl)ethene
Other names
vinyl sulfide, DVS
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
UNII
  • InChI=1S/C4H6S/c1-3-5-4-2/h3-4H,1-2H2
    Key: UIYCHXAGWOYNNA-UHFFFAOYSA-N
  • C=CSC=C
Properties
C4H6S
Molar mass 86.15 g·mol−1
Appearance colorless liquid
Density 0.9098 g/cm3 (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 [77 °F], 100 kPa).

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.[1][2]

It is notable as the product from hydrogen sulfide and acetylene, a combination that arises when acetylene is generated by hydrolysis of technical-grade calcium carbide, which contains impurities of calcium sulfide.[3]

Divinylsulfide was first prepared in 1920 by the reaction of bis(2-chloroethyl)sulfide with sodium ethoxide:[3]

(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.[4] One example is phenyl vinyl sulfide.[5][6] Alkyl ketones react with thiols in the presence of phosphorus pentoxide to give vinyl sulfides:[7]

RSH + CH3C(O)R' → CH2=C(SR)R' + H2O

References

  1. doi:10.1021/ja01358a030
    .
  2. ^ "Divinyl sulfide (FDB012121)". FooDB.
  3. ^
    doi:10.1080/01961778408082463
    .
  4. doi:10.1080/01961779408048961
    .
  5. doi:10.15227/orgsyn.064.0157
    .
  6. doi:10.15227/orgsyn.074.0124
    .
  7. doi:10.1021/ja00353a037
    .
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