Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

View All Documentation

213306

Sigma-Aldrich

Phenyl vinyl sulfoxide

95%

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
C6H5SOCH=CH2
CAS Number:
20451-53-0
Molecular Weight:
152.21
Beilstein/REAXYS Number:
2039218
EC Number:
243-831-6
MDL number:
MFCD00002086
UNSPSC Code:
12352100
PubChem Substance ID:
24852679
NACRES:
NA.22

assay

95%

form

liquid

refractive index

n20/D 1.585 (lit.)

bp

93-95 °C/0.2 mmHg (lit.)

density

1.139 g/mL at 25 °C (lit.)

functional group

sulfoxide

storage temp.

2-8°C

SMILES string

C=CS(=O)c1ccccc1

InChI

1S/C8H8OS/c1-2-10(9)8-6-4-3-5-7-8/h2-7H,1H2

InChI key

MZMJHXFYLRTLQX-UHFFFAOYSA-N

Gene Information

human ... LOC129293(129293)

Looking for similar products? Visit Product Comparison Guide

General description

Phenyl vinyl sulfoxide reacts with lithium enolates of ketones at -78°C in THF to yield bicyclo[n.2.0]alkan-1-ols. It also reacts with in situ generated (dialkylamino)magnesium reagent to yield symmetrical β-(dialkylamino)dithioacetals. It participates as an acetylene equivalent in Diels-Alder reactions.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
69296MJV
S22518
69296MJ
08624EE
09907CW

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

Divinyl sulfone contains hydroquinone as inhibitor, ≥96%

Sigma-Aldrich

V3700

Divinyl sulfone

Diphenyl sulfoxide 96%

Sigma-Aldrich

P35405

Diphenyl sulfoxide

Use of phenyl vinyl sulfoxide as an acetylene equivalent in Diels-Alder cycloadditions.
Paquette LA, et al.
Journal of the American Chemical Society, 100(5), 1597-1599 (1978)
X Ji et al.
Acta crystallographica. Section B, Structural science, 45 ( Pt 1), 93-99 (1989-02-01)
Three diastereomers of bicyclo[2.2.1]hept-5-en-2-yl phenyl sulfoxide were prepared by Diels-Alder [4 + 2] cycloadditions between phenyl vinyl sulfoxide and cyclopentadiene. The isomers were separated by column chromatography on silica gel and repeated recrystallizations gave the pure racemates of three of
Masataka Kawakita et al.
The Journal of organic chemistry, 62(23), 8015-8017 (2001-10-24)
Vinyl sulfoxides (PhSOCR(1)=CHR(2): R(1) = H, Me, or Ph; R(2) = H or Me) were treated with (dialkylamino)magnesium reagents, generated in situ from the reaction of EtMgBr with secondary amines (R(3)R(4)NH: R(3) = Et, i-Pr, or Bn; R(4) = Me
Wendy A Loughlin et al.
Organic & biomolecular chemistry, 1(8), 1347-1353 (2003-08-22)
The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 degrees C in THF react with (+/-)-phenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel

Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service