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804460

Sigma-Aldrich

Potassium 6-bromonicotinoyltrifluoroborate

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Empirical Formula (Hill Notation):
C6H3BBrF3KNO
CAS Number:
Molecular Weight:
291.90
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

form

powder

mp

195.33 °C

SMILES string

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

InChI

1S/C6H3BBrF3NO.K.H/c8-5-2-1-4(3-12-5)6(13)7(9,10)11;;/h1-3H;;

InChI key

ZEDTWTUAQGIVLM-UHFFFAOYSA-N

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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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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