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804673

Sigma-Aldrich

Potassium (2-phenylacetyl)trifluoroborate

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About This Item

Empirical Formula (Hill Notation):
C8H7BF3KO
CAS Number:
1229039-50-2
Molecular Weight:
226.05
MDL number:
MFCD22417243
UNSPSC Code:
12352103
PubChem Substance ID:
329768889

form

powder

mp

178-183 °C (d)

functional group

phenyl

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

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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.

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF5140

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Organotrifluoroborates: Expanding Organoboron Chemistry
Molander GA and Figueroa RF
Aldrichimica Acta, 38(2), 58-58 (2005)
Amide-forming ligation of acyltrifluoroborates and hydroxylamines in water.
Aaron M Dumas et al.
Angewandte Chemie (International ed. in English), 51(23), 5683-5686 (2012-04-28)

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