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901243

Sigma-Aldrich

4-(Acetylamino)phenyl]imidodisulfuryl difluoride

≥98%

Synonym(s):

(4-Acetamidophenyl)(fluorosulfonyl)sulfamoyl fluoride, AISF

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About This Item

Empirical Formula (Hill Notation):
C8H8F2N2O5S2
CAS Number:
2172794-56-6
Molecular Weight:
314.29
UNSPSC Code:
12352101
NACRES:
NA.22

Quality Level

100

Assay

≥98%

form

powder or crystals

mp

146-149 °C

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Application

4-(Acetylamino)phenyl]imidodisulfuryl difluoride (AISF) is a shelf-stable, crystalline reagent for synthesis of fluorosulfates and sulfamoyl fluorides via reaction with phenol and amine nucleophiles. A convenient alternative to the toxic sulfuryl fluoride gas traditionally required for installation of the valuable -SO2F functional group, the solid reagent AISF will find wide utility in preparation of synthetic precursors as well as chemical biology, polymer chemistry, cross-coupling, and deoxyfluorination applications.

Other Notes

Introduction of a Crystalline, Shelf-Stable Reagent for the Synthesis of Sulfur(VI) Fluorides

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Hua Zhou et al.
Organic letters, 20(3), 812-815 (2018-01-13)
The design, synthesis, and application of [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF), a shelf-stable, crystalline reagent for the synthesis of sulfur(VI) fluorides, is described. The utility of AISF is demonstrated in the synthesis of a diverse array of aryl fluorosulfates and sulfamoyl fluorides

Articles

AISF: A Stable, Solid Alternative to Sulfuryl Fluoride Gas

A solid and bench-stable alternative to sulfuryl fluoride gas has been developed, 4-(Acetylamino)phenyl]imidodisulfuryl difluoride (ASIF). ASIF is a shelf-stable, crystallilne reagent for the installation of the valuable SO2F functional group.

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