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746959

Sigma-Aldrich

Ethenesulfonyl fluoride

95%

Synonym(e):

ESF, Vinyl sulfonyl fluoride

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About This Item

Empirische Formel (Hill-System):
C2H3FO2S
CAS-Nummer:
677-25-8
Molekulargewicht:
110.11
MDL-Nummer:
MFCD00051388
UNSPSC-Code:
12352101
PubChem Substanz-ID:
329765803
NACRES:
NA.22

Qualitätsniveau

100

Assay

95%

Form

liquid

Eignung der Reaktion

reaction type: click chemistry

Brechungsindex

n20/D 1.385

Dichte

1.328 g/mL at 25 °C

SMILES String

O=S(F)(C=C)=O

InChI

1S/C2H3FO2S/c1-2-6(3,4)5/h2H,1H2

InChIKey

BYPHZHGVWNKAFC-UHFFFAOYSA-N

Allgemeine Beschreibung

Ethenesulfonylfluoride is a Michael acceptor used in dyestuffs, functional materials,photoresist materials, lubricating oil additives, and medicinal chemistry. Itexhibits extraordinary reactivity in SuFEx click chemistry and organicsynthesis.

Anwendung

Ethenesulfonyl fluoride can be used as a reactant to synthesize:
  • β-Arylethenesulfonyl fluorides via palladium(II) acetate-catalyzed Heck-Matsuda reaction with arenediazonium tetrafluoroborates.
  • Bisalkylsulfonyl fluoride(BSF) monomers via Michael addition reaction with amines/anilines. BSF monomers are applicable in the synthesis of polysulfonates.
  • Cyclobutane-fused pyridinyl sulfonyl fluorides by photocatalytic [2 + 2] cycloaddition with pyridones or isoquinolones.

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Gefahreneinstufungen

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Flam. Liq. 3 - Muta. 2 - Skin Corr. 1B - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

104.0 °F - closed cup

Flammpunkt (°C)

40 °C - closed cup

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Artikel

SuFEx: Sulfonyl Fluorides that Participate in the Next Click Reaction

In collaboration with K. Barry Sharpless and coworkers, we offer a variety of sulfonyl fluoride reagents that undergo a “Click II” reaction.

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Sharpless Group – Professor Product Portal

The Sharpless Lab pursues useful new reactivity and general methods for selectively controlling chemical reactions.

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