Biology:Vinyl sulfone

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Vinyl sulfone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 201-057-6
558721
UNII
UN number 2810 (DIVINYL SULFONE)
Properties
C4H6O2S
Molar mass 118.15 g·mol−1
Appearance colorless oil
Density 1.177 g cm−3
Melting point -26 °C
Boiling point 90–92 °C (194–198 °F; 363–365 K) 8 mmHg
Hazards
GHS pictograms GHS05: CorrosiveGHS06: ToxicGHS07: HarmfulGHS08: Health hazard
GHS Signal word Danger
H300, H310, H314, H315, H335, H341
P203Script error: No such module "Preview warning".Category:GHS errors, P260, P261, P262, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P270, P271, P280, P301+316Script error: No such module "Preview warning".Category:GHS errors, P301+330+331, P302+352, P302+361+354Script error: No such module "Preview warning".Category:GHS errors, P304+340, P305+354+338Script error: No such module "Preview warning".Category:GHS errors, P316Script error: No such module "Preview warning".Category:GHS errors, P317Script error: No such module "Preview warning".Category:GHS errors, P318Script error: No such module "Preview warning".Category:GHS errors, P319Script error: No such module "Preview warning".Category:GHS errors, P321, P330, P332+317Script error: No such module "Preview warning".Category:GHS errors, P361+364Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, P363
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

A vinyl sulfone is an organic compound with the formula O
2S(CH=CH
2)
2. The molecule consisting of two vinyl groups bonded to a sulfone. It is the parent of several vinyl sulfones of the type O
2S(CH=CH
2)R.[1] Many vinyl sulfones are known.

Vinyl sulfones

Examples include phenyl vinyl sulfone,[2] methyl vinyl sulfone,[3] and ethyl vinyl sulfone.[4]

Preparation

Divinyl sulfone is prepared from the diacetate bis(2-hydroxyethyl)sulfide. Oxidation of this diester with hydrogen peroxide gives the sulfone. The sulfone is then pyrolyzed to induce elimination of two equivalents of acetic acid:[5]

(AcOCH
2CH
2)
2SO
2 → (CH
2=CH)
2SO
2 + 2 HOAc (Ac = acetyl)

Other vinyl sulfones are prepared analogously to the vinyl sulfone, i.e. by H2O2-oxidation of the sulfide.[6]

Reactions and uses

Vinyl sulfones are dienophiles. Subsequent to the cycloaddition to a vinyl sulfone, the phenylsulfonyl group can be removed by reduction with zinc.[7]

Vinyl sulfones are Michael acceptors.[8] Vinyl sulfones add thiols, such as cysteine residues.[9] This same reactive nature is responsible for their major industrial use in vinyl sulfone dyes.[10]

Phenyl vinyl sulfone has been applied to ruthenium chemistry as part of olefin metathesis reactions.[11]

Vinyl sulfone has applications to protein purification, especially when linked with mercaptoethanol.[12]

Commercial applications

Vinyl sulfone has uses as a molluscicide pesticide.[13]

Safety

Like similar compounds, vinyl sulfone is a lacrymator and skin irritant. These properties are somewhat mitigated because of its low volatility.[8]

References

  1. ↑ Leonard, Edward C. (1970). Vinyl and Diene Monomers, Part 3. Wiley-Interscience. p. 1466. 
  2. ↑ Gustavson, Clarence (1952). Reactions of Phenyl Vinyl Sulfone with Organometallic Reagents. Syracuse University. 
  3. ↑ Keith, Lawrence H.; Walters, Douglas B. (1991). The National Toxicology Program's Chemical Data Compendium (Volume 8 ed.). CRC Press. ISBN 9780873717229. https://books.google.com/books?id=3rmiNPNOe0AC&pg=PA585. 
  4. ↑ Leonard, Edward C. (1970). Vinyl and Diene Monomers, Part 3. Wiley-Interscience. p. 1475. 
  5. ↑ Overberger, C. G.; Schoene, D. L.; Kamath, P. M.; Tashlick, Irving (1954). "A Convenient Synthesis of Vinyl Sulfone". The Journal of Organic Chemistry 19 (9): 1486–1489. doi:10.1021/jo01374a012. 
  6. ↑ Leo A. Paquette and Richard V. C. Carr (1986). "Phenyl Vinyl Sulfone and Sulfoxide". Organic Syntheses 64: 157. doi:10.15227/orgsyn.064.0157. 
  7. ↑ Ho-shen Lin and Leo A. Paquette (1989). "Reductive Annulation of Vinyl Sulfones: Bicyclo[4.3.0.]Non-1-En-4-One". Organic Syntheses 67: 163. doi:10.15227/orgsyn.067.0163. 
  8. ↑ 8.0 8.1 Lucchi, Ottorino; Fabbri, Davide; Santoyo-Gonzalez, Francisco; Hernandez-Mateo, Fernando; Lopez-Jaramillo, F. Javier; Ortega-Muñoz, Mariano (2021). "Divinyl Sulfone". Encyclopedia of Reagents for Organic Synthesis. pp. 1–8. doi:10.1002/047084289X.rd476.pub2. ISBN 978-0-471-93623-7. 
  9. ↑ Patterson, Cam; Cyr, Douglas M., eds (2005). Ubiquitin-Proteasome Protocols. Springer Science & Business Media. p. PA7. ISBN 9781592598953. https://books.google.com/books?id=qv3ok4y7-j0C&pg=PA7. 
  10. ↑ Research In Technology Of Synthetic Dyes, Pigments And Intermediates. Engineers India. 2005. ISBN 9788186732519. https://books.google.com/books?id=c98gNFmnnYAC&pg=PA274. 
  11. ↑ Bruneau, Christian; Dixneuf, Pierre H. (2004). Ruthenium Catalysts and Fine Chemistry. Springer Science & Business Media. ISBN 9783540205432. https://books.google.com/books?id=6UP05zXC5ioC&pg=PA101. 
  12. ↑ Scopes, Robert K. (1993). Protein Purification: Principles and Practice. Springer Science & Business Media. p. 184. ISBN 9780387940724. https://books.google.com/books?id=byi_lK0gk6cC&pg=PA184. 
  13. ↑ Pesticides Abstracts. U.S. Environmental Protection Agency, Office of Pesticide Programs, Program Support Division. 1975. 




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