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15151

Sigma-Aldrich

1,1-Bis(phenylsulfonyl)ethylene

≥98.0% (CH)

Synonym(s):

(Ethene-1,1-diyldisulfonyl)dibenzene, 1,1-Bis(benzenesulfonyl)ethylene, 1,1-Bis(phenylsulfonyl)ethene, 1,1′-[Ethenylidenebis(sulfonyl)]bis[benzene]

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About This Item

Empirical Formula (Hill Notation):
C14H12O4S2
CAS Number:
39082-53-6
Molecular Weight:
308.37
Beilstein:
2056786
MDL number:
MFCD00043149
UNSPSC Code:
12352100
PubChem Substance ID:
57647326
NACRES:
NA.22

Assay

≥98.0% (CH)

form

powder

mp

124-126 °C

SMILES string

C=C(S(=O)(=O)c1ccccc1)S(=O)(=O)c2ccccc2

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

InChI key

KABQEPJVQFXVIN-UHFFFAOYSA-N

Application

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

Other Notes

A synthetic equivalent of the ethylene 1,2-dipole; Dienophile for Diels-Alder reactions, review; A useful synthon for neutral homologation of ketones.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Andrea-Nekane R Alba et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(18), 5354-5361 (2010-03-09)
A new, easy, and highly enantioselective method for the synthesis of quaternary alpha-alkyl-alpha-amino acids based on organocatalysis is reported. The addition of oxazolones to 1,1-bis(phenylsulfonyl)ethylene is efficiently catalyzed by simple chiral bases or thioureas. The reaction affords alpha,alpha-disubstituted alpha-amino acid
O. De Lucchi et al.
Tetrahedron Letters, 25, 3643-3643 (1984)
O. De Lucchi et al.
Tetrahedron Letters, 25, 3647-3647 (1984)
Xianghong Liu et al.
Scientific reports, 4, 7452-7452 (2014-12-17)
With Fe2O3 as a proof-of-concept, free-standing nanomembrane structure is demonstrated to be highly advantageous to improve the performance of Li-ion batteries. The Fe2O3 nanomembrane electrodes exhibit ultra-long cycling life at high current rates with satisfactory capacity (808 mAh g(-1) after 1000
O. De Lucchi et al.
Tetrahedron, 44, 6755-6755 (1988)

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