1,1-BIS(PHENYLSULFONYL)ETHYLENE Chemical Properties

Melting point:

124-126 °C

Boiling point:

567.9±46.0 °C(Predicted)

Density 

1.347±0.06 g/cm3(Predicted)

form 

solid

color 

colorless

BRN 

2056786

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

1,1-BIS(PHENYLSULFONYL)ETHYLENE Usage And Synthesis

Uses

1,1-Bis(phenylsulfonyl)ethylene was used in the preparation of α,α-disubstituted alpha-amino acid derivatives.

Application

1,1-Bis(phenylsulfonyl)ethylene (1,1-BPSE) is a powerful Michael acceptor and dienophile; reagent for two-carbon homologation of ketones; synthetic equivalent of ethylene in Diels-Alder reactions and of ethylene 1,2-dipole in cycloadditions^[1].

Preparation

1,1-Bis(phenylsulfonyl)ethylene can be prepared via careful oxidation of the corresponding ketene dithioacetal or via Mannich condensation of bis(phenylsulfonyl)methane with paraformaldehyde and a secondary amine followed by elimination with acids^[2].

storage

1,1-Bis(phenylsulfonyl)ethylene keep dry and refrigerated; potential alkylating agent; use in a fume hood.

References

1. (a) Neplyuev, V. M.; Bazarova, I. M.; Lozinskii, M. O. RCR 1986, 55, 883. (b) De Lucchi, O.; Pasquato, L. T 1988, 44, 6755. (c) Simpkins, N. S. In Sulphones in Organic Synthesis; Pergamon: Oxford, 1993.
2. (a) Carpino, L. A. JOC 1973, 38, 2600. (b) Stetter, H.; Steinbeck, K. LA 1974, 1315.

1,1-BIS(PHENYLSULFONYL)ETHYLENE(39082-53-6)Related Product Information

• PHENYL VINYL SULFOXIDE
• Methyl vinyl sulfone
• METHYLTHIOMETHYL PHENYL SULFONE
• 1,1-BIS(METHYLTHIO)ETHYLENE
• BIS(PHENYLTHIO)METHANE
• MMTS
• BIS(PHENYLSULFONYL)METHANE
• Phenyl vinyl sulfone
• 1,1-BIS(PHENYLSULFONYL)ETHYLENE