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804711 Sigma-Aldrich

Potassium 4-fluorobenzoyltrifluoroborate

  • CAS Number 1590389-14-2

  • Empirical Formula (Hill Notation) C7H4BF4KO

  • Molecular Weight 230.01

  •  PubChem Substance ID 329768891

  •  NACRES NA.22

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Properties

Related Categories Boronic Acids and Derivatives, Chemical Synthesis, Heteroaryl Trifluoroborate Salts, Organometallic Reagents, Trifluoroborate Salts More...
Quality Level   100
form   powder
SMILES string   O=C(B(F)(F)F)C1=CC=C(F)C=C1.[K]
InChI   1S/C7H4BF4O.K.H/c9-6-3-1-5(2-4-6)7(13)8(10,11)12;;/h1-4H;;
InChI key   BDIWURUUSCKZDU-UHFFFAOYSA-N

Description

General description

Potassium 4-fluorobenzoyltrifluoroborate belongs to the potassium acyltrifluoroborate (KAT) group. It can be synthesized from 1-(methoxy(4-fluorophenyl)methyl)-1H-benzotriazole.

Application

Potassium 4-fluorobenzoyltrifluoroborate may be used in the synthesis of MIDA (N-methyliminodiacetic acid) 4-fluorobenzoylboronate. It may also be used in the synthesis of potassium O-(4-benzoyltrifluoroborate)-O’-methylpolyethylene glycols of varying molecular weights.

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.

Packaging

1 g in glass bottle

Other Notes

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
Amide-Forming Ligation of Acyltrifluoroborates and Hydroxylamines in Water

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Jeffrey Bode Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Jeffrey Bode Group – Professor Product Portal
Keywords: Annulations, Asymmetric synthesis, Catalysis, Cross couplings, transformation

Peer-Reviewed Papers
15

References

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