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Sigma-Aldrich

Phenyl vinyl sulfoxide

95%

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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.)

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)

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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.

wgk_germany

WGK 3

flash_point_f

230.0 °F

flash_point_c

110 °C

ppe

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

Certificates of Analysis (COA)

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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
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)
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. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

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