| Identification | Back Directory | [Name]
1,1-BIS(PHENYLSULFONYL)ETHYLENE | [CAS]
39082-53-6 | [Synonyms]
1,1-BIS(PHENYLSULFONYL)ETHYLENE
Benzene, 1,1-ethenylidenebis(sulfonyl)bis-
1,1-Bis(phenylsulfonyl)ethylene >=98.0% (CH) | [Molecular Formula]
C14H12O4S2 | [MDL Number]
MFCD00043149 | [MOL File]
39082-53-6.mol | [Molecular Weight]
308.37 |
| Chemical Properties | Back Directory | [Melting point ]
124-126 °C
| [Boiling point ]
567.9±46.0 °C(Predicted) | [density ]
1.347±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C, stored under nitrogen | [form ]
solid | [color ]
colorless | [BRN ]
2056786 | [InChI]
1S/C14H12O4S2/c1-12(19(15,16)13-8-4-2-5-9-13)20(17,18)14-10-6-3-7-11-14/h2-11H,1H2 | [InChIKey]
KABQEPJVQFXVIN-UHFFFAOYSA-N | [SMILES]
C=C(S(=O)(=O)c1ccccc1)S(=O)(=O)c2ccccc2 |
| Hazard Information | Back Directory | [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.
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