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ALD00422

Sigma-Aldrich

2-Formylphenyl sulfofluoridate

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About This Item

Empirical Formula (Hill Notation):
C7H5FO4S
Molecular Weight:
204.18
UNSPSC Code:
12352100
PubChem Substance ID:
329772674
NACRES:
NA.22

description

Fp: >230°F

Quality Level

100

form

liquid

refractive index

n20/D 1.5086

density

1.4545 g/mL at 25 °C

SMILES string

O=S(OC1=C(C=O)C=CC=C1)(F)=O

InChI

1S/C7H5FO4S/c8-13(10,11)12-7-4-2-1-3-6(7)5-9/h1-5H

InChI key

SUOCJDDQQKVIKZ-UHFFFAOYSA-N

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General description

2-Formylphenyl sulfofluoridate is an aryl fluorosulfate. It can be synthesized from the reaction between phenol and sulfuryl fluoride in the presence of triethylamine. It undergoes Sonogashira coupling reaction with phenyl acetylene.

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 temperature and are not air sensitive.

Other Notes

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

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

No data available

Flash Point(C)

No data available

Certificates of Analysis (COA)

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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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