804673
Potassium (2-phenylacetyl)trifluoroborate
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About This Item
Empirical Formula (Hill Notation):
C8H7BF3KO
CAS Number:
Molecular Weight:
226.05
UNSPSC Code:
12352103
PubChem Substance ID:
MDL number:
InChI
1S/C8H7BF3O.K/c10-9(11,12)8(13)6-7-4-2-1-3-5-7;/h1-5H,6H2;/q-1;+1
SMILES string
[K+].F[B-](F)(F)C(=O)Cc1ccccc1
InChI key
SEOSMCJOPUBHBF-UHFFFAOYSA-N
form
powder
mp
178-183 °C (d)
functional group
phenyl
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
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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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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