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Merck
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Principaux documents

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804452

Sigma-Aldrich

Potassium 3-ethoxycarbonylbenzoyltrifluoroborate

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About This Item

Formule empirique (notation de Hill):
C10H9BF3KO3
Numéro CAS:
1622923-42-5
Poids moléculaire :
284.08
Code UNSPSC :
12352103
ID de substance PubChem :
329768873
Nomenclature NACRES :
NA.22

Forme

powder

Chaîne SMILES 

CCOC(C1=CC=CC(C(B(F)(F)F)=O)=C1)=O.[K]

InChI

1S/C10H9BF3O3.K.H/c1-2-17-10(16)8-5-3-4-7(6-8)9(15)11(12,13)14;;/h3-6H,2H2,1H3;;

Clé InChI

WJLIBYVPNAKYHP-UHFFFAOYSA-N

Application

Acyltrifluroborates (KAT′s) 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.

Autres remarques

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number

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David M Nickerson et al.
Chemical communications (Cambridge, England), 49(39), 4289-4291 (2012-12-01)
The strategic incorporation of internal Lewis acids onto urea scaffolds gives rise to a family of tunable hydrogen bond donor catalysts. The nature of the Lewis acid and associated ligands affects the urea polarization, acidity, and activity in reactions of
Sonia S So et al.
Organic letters, 14(2), 444-447 (2012-01-03)
Boronate ureas operate as catalysts for the activation of nitrocyclopropane carboxylates in nucleophilic ring-opening reactions. A variety of amines were found to open the urea-activated nitrocyclopropane carboxylates, generating highly useful nitro ester building blocks in good yields. Standard manipulations allow
Tyler J Auvil et al.
Angewandte Chemie (International ed. in English), 52(43), 11317-11320 (2013-09-17)
It takes two: A unique organocatalyzed cascade for the unsymmetric double arylation of α-nitrodiazoesters is described. This organocascade features the strategic use of carbene-activating anilines in conjunction with a urea catalyst, thus allowing for the synthesis of pharmaceutically attractive α-diarylesters
Sonia S So et al.
The Journal of organic chemistry, 79(11), 4832-4842 (2014-05-07)
The power of hydrogen-bond donor catalysis has been harnessed to elicit and control carbene-like reactivity from nitrodiazoesters. Specifically, select ureas have been identified as effective catalysts for N-H insertion and multicomponent coupling reactions of nitrodiazoesters, anilines, and aromatic nucleophiles, thereby
Sonia S So et al.
Organic letters, 13(4), 716-719 (2011-01-14)
Boronate ureas are introduced as a new class of noncovalent catalysts for conjugate addition reactions with enhanced activity. Through intramolecular coordination of the urea functionality to a strategically placed Lewis acid, rate enhancements up to 10 times that of more
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