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804673 Sigma-Aldrich

Potassium (2-phenylacetyl)trifluoroborate

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Properties

Related Categories Aryl Trifluoroborate Salts, Boronic Acids and Derivatives, Chemical Synthesis, Heteroaryl Trifluoroborate Salts, Organometallic Reagents,
Quality Level   100
form   powder
mp   178-183 °C (d)
SMILES string   [K+].F[B-](F)(F)C(=O)Cc1ccccc1
InChI   1S/C8H7BF3O.K/c10-9(11,12)8(13)6-7-4-2-1-3-5-7;/h1-5H,6H2;/q-1;+1
InChI key   SEOSMCJOPUBHBF-UHFFFAOYSA-N

Description

General description

Potassium (2-phenylacetyl)trifluoroborate (potassium benzyltrifluoroborate, phenylacetyl trifluoroborate) belongs to the class of compounds known as potassium acyltrifluroborates (KATs). This trifluoroborate salt is stable and does not readily undergo trimerization. It undergoes palladium-catalyzed cross-coupling reaction with p-nitro triflate to form the corresponding biaryl. Phenylacetyl trifluoroborate acts as an acyl donor during the amidation of O-benzoyl hydroxylamine to form the corresponding amide.

Application

Potassium acyltrifluroborates (KATs) are bench, air and moisture stable reagents for rapid chemoselective amide bond formations with hydroxylamines. These amide bond forming reactions proceed under aqueous conditions without the need for coupling reagents or protecting groups. This product was introduced in collaboration with the Bode Research Group.

Packaging

500 mg in glass bottle

Other Notes

Rapid Ligations with Equimolar Reactants in Water with the Potassium Acyltrifluoroborate (KAT) Amide Formation
Amide-Forming Ligation of Acyltrifluoroborates and Hydroxylamines in Water
Synthesis of Chemically and Configurationally Stable Monofluoro Acylboronates: Effect of Ligand Structure on their Formation, Properties, and Reactivities

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Jeffrey Bode Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Jeffrey Bode Group – Professor Product Portal
Keywords: Annulations, Asymmetric synthesis, Catalysis, Cross couplings, transformation

Peer-Reviewed Papers
15

References

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