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901243

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
Assay:
≥98%
Form:
powder or crystals
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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

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

Technology Spotlight

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

901243-1G: + 901243-BULK: + 901243-5G: + 901243-VAR: + 901243-25G:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF8040V
WXBF4272V
WXBF2213V
WXBF0709V
WXBF2402V

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Articles

AISF：固体のスルフリルフッ素化試薬

AISFは、実験環境で安定であり、有機合成でSO2F基を導入するためのスルフリルフルオリドガスの代わりに使用できます。

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.

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