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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
MDL number:
MFCD31625434
UNSPSC Code:
12352101
NACRES:
NA.22

Quality Level

100

assay

≥98%

form

powder or crystals

mp

146-149 °C

functional group

amide

SMILES string

F[S](=O)(=O)N([S](=O)(=O)F)c1ccc(cc1)NC(=O)C

InChI key

SMMIWAIOWMUFCR-UHFFFAOYSA-N

Related Categories

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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Description
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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF4272V
WXBF2213V
WXBF0709V
WXBF2402V
WXBD9543V

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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 Solid Alternative to Sulfuryl Fluoride Gas

ASIF provides bench-stable alternative to sulfuryl fluoride gas for installing SO2F functional group in organic synthesis.

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