| Identification | Back Directory | [Name]
PHENYL VINYL SULFOXIDE | [CAS]
20451-53-0 | [Synonyms]
NISTC20451530
(Vinylsulfinyl)benzene
PHENYL VINYL SULFOXIDE
VINYL PHENYL SULFOXIDE
phenyl vinyl sulphoxide
Sulfoxide, phenyl vinyl
(Ethenylsulfinyl)benzene
Phenyl ethenyl sulfoxide
Phenyl (ethenyl) sulfoxide
Benzene, (ethenylsulfinyl)- | [EINECS(EC#)]
243-831-6 | [Molecular Formula]
C8H8OS | [MDL Number]
MFCD00002086 | [MOL File]
20451-53-0.mol | [Molecular Weight]
152.21 |
| Chemical Properties | Back Directory | [Boiling point ]
93-95 °C0.2 mm Hg(lit.)
| [density ]
1.139 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.585(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [solubility ]
sol most organic solvents | [form ]
liquid
| [color ]
deeply yellow
| [BRN ]
2039218 | [InChI]
1S/C8H8OS/c1-2-10(9)8-6-4-3-5-7-8/h2-7H,1H2 | [InChIKey]
MZMJHXFYLRTLQX-UHFFFAOYSA-N | [SMILES]
C=CS(=O)c1ccccc1 |
| Hazard Information | Back Directory | [Uses]
Phenyl vinyl sulfoxide is used as acetylene equivalent in Diels-Alder, dipolar cycloaddition, and Michael reactions; can be deprotonated to the unsaturated α-sulfinyl carbanion; undergoes additive Pummerer reactions.
| [Preparation]
Phenyl vinyl sulfoxide can be prepared by reaction of a carbanion with chiral arylsulfinates derived from menthol or glucose, or N-sulfinyloxazolidinones of norephedrine or phenylalanine, or by sequential arylation-vinylation of sulfites derived from lactic acid or aminosulfites derived from ephedrine (99+% ee).
| [Synthesis Reference(s)]
The Journal of Organic Chemistry, 61, p. 2260, 1996 DOI: 10.1021/JO960178X | [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. | [Precautions]
As with most optically active sulfoxides, Phenyl vinyl sulfoxide racemizes in the presence of acids. Use in a fume hood.
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| Company Name: |
Energy Chemical
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| Tel: |
021-021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
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