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213306

Sigma-Aldrich

Phenyl vinyl sulfoxide

95%

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About This Item

Formule linéaire :
C6H5SOCH=CH2
Numéro CAS:
20451-53-0
Poids moléculaire :
152.21
Numéro Beilstein :
2039218
Numéro CE :
243-831-6
Numéro MDL:
MFCD00002086
Code UNSPSC :
12352100
ID de substance PubChem :
24852679
Nomenclature NACRES :
NA.22

Pureté

95%

Forme

liquid

Indice de réfraction

n20/D 1.585 (lit.)

Point d'ébullition

93-95 °C/0.2 mmHg (lit.)

Densité

1.139 g/mL at 25 °C (lit.)

Groupe fonctionnel

sulfoxide

Température de stockage

2-8°C

Chaîne SMILES 

C=CS(=O)c1ccccc1

InChI

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

Clé InChI

MZMJHXFYLRTLQX-UHFFFAOYSA-N

Informations sur le gène

human ... LOC129293(129293)

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Description générale

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.

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

230.0 °F - closed cup

Point d'éclair (°C)

110 °C - closed cup

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

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

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Sigma-Aldrich

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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
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)
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.

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.

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.

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.

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