Divinyl sulfide
| Names | |
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| Preferred IUPAC name
(Ethenylsulfanyl)ethene | |
| Other names
vinyl sulfide, DVS
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
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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]
Preparation
[edit | edit source]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
[edit | edit source]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
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