CAS 5535-48-8|(ethenesulfonyl)benzene|Phenyl vinyl sulfone|(ethenesulfonyl)benzene|Phenyl vinyl sulfone|苯基乙烯基砜|(ethenesulfonyl)benzene

General Information

Structure

Molecular Formula

C₈H₈O₂S

Molecular Mass

168.21292

Exact Mass

168.0245005

Charge

InChI

InChI=1S/C8H8O2S/c1-2-11(9,10)8-6-4-3-5-7-8/h2-7H,1H2

InChIKey

UJTPZISIAWDGFF-UHFFFAOYSA-N

Canonic Smiles

C=CS(=O)(=O)c1ccccc1

Isomeric Smiles

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

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

1.5459023

LogD (pH = 7.4)

1.5459023

Log P

1.5459023

Molar Refractivity

43.5982

Polarizability

17.903816

Polar Surface Area

34.14

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

(ethenesulfonyl)benzene

Synonyms

Phenyl vinyl sulfonePhenyl vinyl sulfone苯基乙烯基砜(ethenesulfonyl)benzene

IUPAC name

(ethenesulfonyl)benzene

Names and Identifiers

Registration numbers

MDL Number

MFCD00007554

CAS Number

5535-48-8

PubChem SID

248874402488743916203575824854323

Beilstein Number

1906894

EC Number

226-890-2

PubChem CID

79664

Registration numbers

Properties

Pharmacology Properties

human ... LOC129293(129293)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

241717

Packaging
1, 5 g in glass bottle
Application
Common reagent used in a variety of cycloaddition reactions to form cyclopropanes,1 cyclohexenes,2,3 and cyclooctadienes.4

79293

Other Notes
Dienophile; adducts can conveniently be transformed into alkanes or ketones (equivalent of ethylene or ketene), review1

Molecule Details

References

PubChem Literature

From Data Sources

• Undergoes the Baylis-Hillman reaction (addition to aldehydes in the presence of 1,4-Diazabicyclo[2.2.2]octane, A14003): Tetrahedron, 44, 6095 (1988).

• Reactive dienophile. Can function as an acetylene equivalent if benzenesulfinic acid is eliminated thermally from the Diels-Alder adduct to form an olefinic double bond: J. Am. Chem. Soc., 100, 1597 (1978).

• Can also behave as an activated form of ethylene if the sulfone group is cleaved from the adduct, e.g. with Na amalgam, with the possibility of prior alkylation of the adduct: J. Org. Chem., 48, 4976 (1983):

• For addition to 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, L06100, see: J. Org. Chem., 48, 4986 (1983). Addition to steroids with a cyclopentadienoid D-ring, followed by cleavage of the resulting alkene, gives the diformyl derivatives, useful for further functionalization: J. Chem. Soc., Perkin 1, 241 (1990).

• See also Divinyl sulfone, L12827.

• For use in a 1,3-dipolar cycloaddition reaction, see 3-Hydroxypyridine, A13910.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

(ethenesulfonyl)benzene

Synonyms

Phenyl vinyl sulfonePhenyl vinyl sulfone苯基乙烯基砜(ethenesulfonyl)benzene

IUPAC name

(ethenesulfonyl)benzene

Registration numbers

MDL Number

MFCD00007554

CAS Number

5535-48-8

PubChem SID

248874402488743916203575824854323

Beilstein Number

EC Number

PubChem CID

Molecule Details

241717

Packaging
1, 5 g in glass bottle
Application
Common reagent used in a variety of cycloaddition reactions to form cyclopropanes,1 cyclohexenes,2,3 and cyclooctadienes.4

79293

Other Notes
Dienophile; adducts can conveniently be transformed into alkanes or ketones (equivalent of ethylene or ketene), review1

References

PubChem Literature

From Data Sources

• Undergoes the Baylis-Hillman reaction (addition to aldehydes in the presence of 1,4-Diazabicyclo[2.2.2]octane, A14003): Tetrahedron, 44, 6095 (1988).

• See also Divinyl sulfone, L12827.

• For use in a 1,3-dipolar cycloaddition reaction, see 3-Hydroxypyridine, A13910.

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

human ... LOC129293(129293)

Molecule

ID:70033