Divinyl sulfide

Divinyl sulfide
Names
	Other names vinyl sulfide, DVS
Identifiers
CAS Number	627-51-0;
3D model (JSmol)	Interactive image;
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

Divinyl sulfide is the organosulfur compound with the formula S(CH=CH₂)₂. It is a colorless liquid with a faint odor. It is found in the oil of 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 sulfur mustard with sodium ethoxide:[3]

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

A variety of monovinyl sulfides are known, often arising from the reactions of thiols and acetylenes.[4]

References

Ruigh, William L.; Major, Randolph T. (1931). "The Preparation and Properties of Pure Divinyl Ether". Journal of the American Chemical Society. 53 (7): 2662–2671. doi:10.1021/ja01358a030.
"Divinyl sulfide (FDB012121)". FooDB.
Boris A. Trofimov, S. V. Amosova (1984). "Divinyl Sulfide: Synthesis, Properties, and Applications". Sulfur Reports. 3 (9): 323–393. doi:10.1080/01961778408082463.CS1 maint: uses authors parameter (link)
Nina A. Nedolya, Boris A. Trofimov (1994). "Sulfur-containing vinyl ethers". Sulfur Reports. 15 (2): 237–316. doi:10.1080/01961779408048961.CS1 maint: uses authors parameter (link)

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[1] Ruigh, William L.; Major, Randolph T. (1931). "The Preparation and Properties of Pure Divinyl Ether". Journal of the American Chemical Society. 53 (7): 2662–2671. doi:10.1021/ja01358a030.

[2] "Divinyl sulfide (FDB012121)". FooDB.

[Trofimov-3] Boris A. Trofimov, S. V. Amosova (1984). "Divinyl Sulfide: Synthesis, Properties, and Applications". Sulfur Reports. 3 (9): 323–393. doi:10.1080/01961778408082463.CS1 maint: uses authors parameter (link)

[4] Nina A. Nedolya, Boris A. Trofimov (1994). "Sulfur-containing vinyl ethers". Sulfur Reports. 15 (2): 237–316. doi:10.1080/01961779408048961.CS1 maint: uses authors parameter (link)