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901243

Sigma-Aldrich

4-(Acetylamino)phenyl]imidodisulfuryl difluoride

≥98%

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Synonym(s):
(4-Acetamidophenyl)(fluorosulfonyl)sulfamoyl fluoride, AISF
Empirical Formula (Hill Notation):
C8H8F2N2O5S2
CAS Number:
2172794-56-6
Molecular Weight:
314.29

Quality Level

100

Assay

≥98%

form

powder or crystals

mp

146-149 °C

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This Item
AX1235437646ALD00132
4-(Acetylamino)phenyl]imidodisulfuryl difluoride ≥98%

Sigma-Aldrich

901243

4-(Acetylamino)phenyl]imidodisulfuryl difluoride

Ammonium Bifluoride Practical

Supelco

AX1235

Ammonium Bifluoride

Sodium hydrogen difluoride granular, 98%

Sigma-Aldrich

437646

Sodium hydrogen difluoride

4-Phenoxybenzenesulfonyl fluoride 95%

Sigma-Aldrich

ALD00132

4-Phenoxybenzenesulfonyl fluoride

form

powder or crystals

form

flakes

form

granular

form

solid

mp

146-149 °C

mp

126 °C

mp

-

mp

45-49 °C

Quality Level

100

Quality Level

200

Quality Level

-

Quality Level

100

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. This product was introduced collaboratively with Pfizer and BioDuro.

Other Notes

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

Technology Spotlight

related product

Product No.
Description
Pricing

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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