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213306 Sigma-Aldrich

Phenyl vinyl sulfoxide

95%

  • CAS Number 20451-53-0

  • Linear Formula C6H5SOCH=CH2

  • Molecular Weight 152.21

  •  Beilstein/REAXYS Number 2039218

  •  EC Number 243-831-6

  •  MDL number MFCD00002086

  •  PubChem Substance ID 24852679

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, Chemical Synthesis, Organic Building Blocks, Sulfoxides, Sulfur Compounds More...
assay   95%
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)

Description

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.

Packaging

5 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Flash Point(F) 
230 °F
Flash Point(C) 
110 °C

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Protocols & Articles

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 vi...
Keywords: Addition reactions, Asymmetric synthesis, Building blocks, Catalysis, Cycloadditions, Diels-Alder reaction, Immobilization

Peer-Reviewed Papers
15

References

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