767441
Potassium [(4-methoxybenzyloxy)methyl]trifluoroborate
97%
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About This Item
Empirical Formula (Hill Notation):
C9H11BF3KO2
CAS Number:
Molecular Weight:
258.09
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Assay
97%
form
solid
mp
203-213 °C
functional group
ether
SMILES string
[K+].COc1ccc(COC[B-](F)(F)F)cc1
InChI
1S/C9H11BF3O2.K/c1-14-9-4-2-8(3-5-9)6-15-7-10(11,12)13;/h2-5H,6-7H2,1H3;/q-1;+1
InChI key
HWHMOMQODHUMRW-UHFFFAOYSA-N
Application
Alkoxymethyltrifluoroborate undergoes palladium-catalyzed carbon-carbon bond formation (Suzuki-Miyuara reaction) with aryl chlorides to provide a non-traditional disconnection for the preparation of aryl- and heteroaryl ethers.
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
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Gary A Molander et al.
Organic letters, 10(11), 2135-2138 (2008-04-29)
A wide variety of alkoxymethyltrifluoroborate substrates were prepared via SN2 displacement of potassium bromomethyltrifluoroborate with various alkoxides in excellent yields. These alkoxymethyltrifluoroborates were effectively cross-coupled with several aryl chlorides. This method provides a unique dissonant disconnect that allows greater flexibility
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