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Merck
CN

804991

Sigma-Aldrich

Potassium 3-quinolinoyltrifluoroborate

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About This Item

Empirical Formula (Hill Notation):
C10H6BF3KNO
CAS Number:
1622923-60-7
Molecular Weight:
263.07
UNSPSC Code:
12352103
PubChem Substance ID:
329768915
NACRES:
NA.22

Key Documents

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form

powder

mp

87-92 °C

SMILES string

O=C([B-](F)(F)F)C1=CC(C=CC=C2)=C2N=C1.[K+]

InChI

1S/C10H6BF3NO.K/c12-11(13,14)10(16)8-5-7-3-1-2-4-9(7)15-6-8;/h1-6H;/q-1;+1

InChI key

GFHZIIJGNIFLTM-UHFFFAOYSA-N

General description

Potassium 3-quinolinoyltrifluoroborate is a potassium acyltrifluoroborate (KAT). They readily undergo chemoselective amide-bond formation reactions.

Application

Potassium 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

Precautionary Statements

P305 + P351 + P338

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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Hidetoshi Noda et al.
Journal of the American Chemical Society, 136(15), 5611-5614 (2014-04-02)
The identification of fast, chemoselective bond-forming reactions is one of the major contemporary challenges in chemistry. We show that chemoselective amide-forming ligations of potassium acyltrifluoroborates (KATs) and O-carbamoylhydroxylamines proceed in the presence of all unprotected functional groups with a second-order

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