Vinyl sulfone

From Wikipedia, the free encyclopedia

Vinyl sulfone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 201-057-6
558721
UNII
UN number 2810 (DIVINYL SULFONE)
  • InChI=1S/C4H6O2S/c1-3-7(5,6)4-2/h3-4H,1-2H2
    Key: AFOSIXZFDONLBT-UHFFFAOYSA-N
  • C=CS(=O)(=O)C=C
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 labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H300, H310, H314, H315, H335, H341
P203, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P361+P364, P362+P364, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

A vinyl sulfone is an organic compound with the formula O2S(CH=CH2)2. The molecule consisting of two vinyl groups bonded to a sulfone. It is the parent of several vinyl sulfones of the type O2S(CH=CH2)R.[1] Many vinyl sulfones are known.

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]

(AcOCH2CH2)2SO2 → (CH2=CH)2SO2 + 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

Safety

References

Related Articles

Wikiwand AI