739588
Potassium 2-methoxypyrimidin-5-yl-5-trifluoroborate
90%
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About This Item
Empirical Formula (Hill Notation):
C5H5BF3KN2O
CAS Number:
Molecular Weight:
216.01
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
Assay
90%
form
solid
mp
239-254 °C
SMILES string
[K+].COc1ncc(cn1)[B-](F)(F)F
InChI
1S/C5H5BF3N2O.K/c1-12-5-10-2-4(3-11-5)6(7,8)9;/h2-3H,1H3;/q-1;+1
InChI key
ACPITJHSWGPRRF-UHFFFAOYSA-N
Application
Potassium 2-methoxypyrimidin-5-yl-5-trifluoroborate can be used as a substrate in:
- Metal-free synthesis of biaryls through oxidative electrocoupling reaction.
- Cross-coupling reactions with unactivated alkyl halides in the presence of a nickel catalyst.
- Suzuki-Miyaura coupling with aryl and heteroaryl halides using a palladium catalyst.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
Certificates of Analysis (COA)
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Arif Music et al.
Journal of the American Chemical Society, 142(9), 4341-4348 (2020-02-11)
We report herein versatile, transition metal-free and additive-free (hetero)aryl-aryl coupling reactions promoted by the oxidative electrocoupling of unsymmetrical tetra(hetero)arylborates (TABs) prepared from ligand-exchange reactions on potassium trifluoroarylborates. Exploiting the power of electrochemical oxidations, this method complements the existing organoboron toolbox.
Nickel-catalyzed cross-coupling of potassium aryl-and heteroaryltrifluoroborates with unactivated alkyl halides
Molander GA, et al.
Organic Letters, 12(24), 5783-5785 (2010)
Electrochemical Synthesis of Biaryls via Oxidative Intramolecular Coupling of Tetra(hetero)arylborates
Music A, et al.
Journal of the American Chemical Society, 142(9), 4341-4348 (2020)
Scope of the Suzuki- Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates
Molander GA, et al.
The Journal of Organic Chemistry, 74(3), 973-980 (2009)
Gary A Molander et al.
Organic letters, 12(24), 5783-5785 (2010-11-26)
A method for the cross-coupling of alkyl electrophiles with various potassium aryl- and heteroaryltrifluoroborates has been developed. Nearly stoichiometric amounts of organoboron species could be employed to cross-couple a large variety of challenging heteroaryl nucleophiles. Several functional groups were tolerated
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