Divinyl sulfide

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]

Divinyl sulfide

Names
Preferred IUPAC name (Ethenylsulfanyl)ethene
Other names vinyl sulfide, DVS
Identifiers
CAS Number	627-51-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:177668
ChemSpider	11817
PubChem CID	12321
UNII	CL87X0NVJA
CompTox Dashboard (EPA)	DTXSID10211766
InChI InChI=1S/C4H6S/c1-3-5-4-2/h3-4H,1-2H2 Key: UIYCHXAGWOYNNA-UHFFFAOYSA-N
SMILES C=CSC=C
Properties
Chemical formula	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). Infobox references

Preparation

Divinyl sulfide is formed from hydrogen sulfide and acetylene.^[2] Divinylsulfide can arise when inadvertently when acetylene is generated by hydrolysis of technical-grade calcium carbide contaminated with 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