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ALD00420

Sigma-Aldrich

2-cyanophenyl sulfofluoridate

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500 MG
$13.96

About This Item

Empirical Formula (Hill Notation):
C7H4FNO3S
Molecular Weight:
201.17
MDL number:
MFCD29472039
UNSPSC Code:
12352100
PubChem Substance ID:
329772673
NACRES:
NA.22

$13.96

List Price$14.70Save 5%
Web-Only Promotion

Available to ship onApril 29, 2025Details

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form

liquid

Quality Level

100

SMILES string

O=S(F)(OC1=CC=CC=C1C#N)=O

InChI

1S/C7H4FNO3S/c8-13(10,11)12-7-4-2-1-3-6(7)5-9/h1-4H

InChI key

FWHISILUCPTNBH-UHFFFAOYSA-N

Related Categories

General description

2-Cyanophenyl sulfofluoridate is an aryl fluorosulfate. It undergoes Suzuki-Miyaura reaction with aryl boronic acid in the presence of Pd(OAc)2 and Et3N to afford the corresponding biaryl derivative. 2-Cyanophenyl sulfofluoridate can be synthesized from the reaction between phenol and sulfuryl fluoride in the presence of triethylamine.[1]

Application

The following aryl fluorosulfate can be utilized as a cross-coupling partner in Suzuki-Miyaura reactions. The standard reaction conditions for these palladium-catalyzed C-C bond formations are ligand-free and can be performed in water, at room temperatre and are not air sensitive.

Other Notes

Palladium-Catalyzed, Ligand-Free Suzuki Reaction in Water Using Aryl Fluorosulfates

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Qiaobin Liang et al.
Organic letters, 17(8), 1942-1945 (2015-04-10)
Aryl fluorosulfates were prepared by a simple method and employed as coupling partners in the Suzuki-Miyaura reaction. The cross-coupling reactions were performed in water under air at room temperature without ligands or additives such as surfactants or phase-transfer reagents and

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