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804681

Sigma-Aldrich

Potassium 5-hydroxypentanoyltrifluoroborate

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Empirical Formula (Hill Notation):
C5H9BF3KO2
CAS Number:
Molecular Weight:
208.03
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

mp

123.6 °C

SMILES string

[K+].OCCCCC(=O)[B-](F)(F)F

InChI

1S/C5H9BF3O2.K/c7-6(8,9)5(11)3-1-2-4-10;/h10H,1-4H2;/q-1;+1

InChI key

OLLDPQQFLCSTQN-UHFFFAOYSA-N

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General description

Potassium 5-hydroxypentanoyltrifluoroborate belongs to the class of compounds known as potassium acyltrifluroborates (KATs). It acts as an acyl donor during the amidation of O-benzoyl hydroxylamine to form the corresponding amide product.

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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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