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About This Item
Empirical Formula (Hill Notation):
C7H4FNO3S
Molecular Weight:
201.17
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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form
liquid
Quality Level
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.
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.
signalword
Warning
hcodes
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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