Skip to Content
Merck
All Photos(1)

Key Documents

ALD00420

Sigma-Aldrich

2-cyanophenyl sulfofluoridate

Sign Into View Organizational & Contract Pricing


About This Item

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

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

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service