804681
Potassium 5-hydroxypentanoyltrifluoroborate
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About This Item
Empirical Formula (Hill Notation):
C5H9BF3KO2
CAS Number:
Molecular Weight:
208.03
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
Form:
powder
InChI
1S/C5H9BF3O2.K/c7-6(8,9)5(11)3-1-2-4-10;/h10H,1-4H2;/q-1;+1
SMILES string
[K+].OCCCCC(=O)[B-](F)(F)F
InChI key
OLLDPQQFLCSTQN-UHFFFAOYSA-N
form
powder
mp
123.6 °C
functional group
hydroxyl
Quality Level
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.
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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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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