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Merck

901243

4-(Acetylamino)phenyl]imidodisulfuryl difluoride

≥98%

Synonym(s):

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

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CLP 149,000

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CLP 539,000

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CLP 1,330,000

CLP 149,000

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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

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Product Name

4-(Acetylamino)phenyl]imidodisulfuryl difluoride, ≥98%

InChI key

SMMIWAIOWMUFCR-UHFFFAOYSA-N

SMILES string

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

assay

≥98%

form

powder or crystals

mp

146-149 °C

functional group

amide

Quality Level

100

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This Item
ALD00132437646ALD00036
4-(Acetylamino)phenyl]imidodisulfuryl difluoride ≥98%

Sigma-Aldrich

901243

4-(Acetylamino)phenyl]imidodisulfuryl difluoride

4-Phenoxybenzenesulfonyl fluoride 95%

Sigma-Aldrich

ALD00132

4-Phenoxybenzenesulfonyl fluoride

Sodium hydrogen difluoride granular, 98%

Sigma-Aldrich

437646

Sodium hydrogen difluoride

4-Nitrobenzenesulfonyl fluoride 95%

Sigma-Aldrich

ALD00036

4-Nitrobenzenesulfonyl fluoride

assay

≥98%

assay

95%

assay

98%

assay

95%

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

mp

146-149 °C

mp

45-49 °C

mp

-

mp

75-80 °C, 78-80 °C (lit.)

form

powder or crystals

form

solid

form

granular

form

solid

functional group

amide

functional group

-

functional group

-

functional group

-

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
Pricing

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF8040V
WXBF4272V
WXBF2213V
WXBF0709V
WXBF2402V

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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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