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804363

Sigma-Aldrich

Potassium 4-anisoyltrifluoroborate

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About This Item

Empirical Formula (Hill Notation):
C8H7BF3KO2
CAS Number:
1622923-47-0
Molecular Weight:
242.04
UNSPSC Code:
12352103
PubChem Substance ID:
329768864
NACRES:
NA.22

form

powder

Quality Level

100

SMILES string

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

InChI

1S/C8H7BF3O2.K.H/c1-14-7-4-2-6(3-5-7)8(13)9(10,11)12;;/h2-5H,1H3;;

InChI key

VXVQBCXLJYVTDZ-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.

Other Notes

Amide-Forming Ligation of Acyltrifluoroborates and Hydroxylamines in Water
Rapid Ligations with Equimolar Reactants in Water with the Potassium Acyltrifluoroborate (KAT) Amide Formation
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Related Content

Bode Group – Professor Product Portal

The Bode Group aims to develop new reactions and reagents for the synthesis of complex molecules. The Bode Group has developed N-mesityl-substituted NHCs as organocatalysts for the catalytic generation of reactive species including activated carboxylates, homoenolates, and enolates. These novel catalysts and reactions have made possible a new generation of highly enantioselective annulations from simple starting materials under mild reaction conditions, usually at room temperature and without added reagents. Furthering the goal of designing new reagents to enable the assembly of complex molecules, the Bode group has developed SnAP reagents for the facile, one-pot conversion of aldehydes into N-unprotected, saturated N-heterocycles, including bicyclic and spirocyclic structures. These easy to handle reagents provide a simple and robust alternative to the challenging and restrictive cross-coupling methods for the functionalization of saturated N-heterocycles.

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