4-(Acetylamino)phenyl]imidodisulfuryl difluoride

Name: 4-(Acetylamino)phenyl]imidodisulfuryl difluoride
Brand: ALDRICH
Price: 109.5 USD
Availability: InStock

≥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

Key Documents

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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

Related Categories

Chemical Synthesis

Halogenation Reagents

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This Item	ALD00132	437646	ALD00036
Sigma-Aldrich 901243 4-(Acetylamino)phenyl]imidodisulfuryl difluoride	Sigma-Aldrich ALD00132 4-Phenoxybenzenesulfonyl fluoride	Sigma-Aldrich 437646 Sodium hydrogen difluoride	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

Technology Spotlight

related product

Product No.

Description

Pricing

903132

1-(Fluorosulfonyl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate, ≥95%

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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

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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4-(Acetylamino)phenyl]imidodisulfuryl difluoride