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773034

Sigma-Aldrich

Potassium (3-butenyl)trifluoroborate

90%

Synonym(s):

Potassium homoallyltrifluoroborate

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About This Item

Empirical Formula (Hill Notation):
C4H7BF3K
CAS Number:
608140-67-6
Molecular Weight:
162.00
MDL number:
MFCD11052817
UNSPSC Code:
12352103
PubChem Substance ID:
329767597
NACRES:
NA.22

Quality Level

100

assay

90%

form

solid

mp

>300 °C

SMILES string

[K+].F[B-](F)(F)CCC=C

InChI

1S/C4H7BF3.K/c1-2-3-4-5(6,7)8;/h2H,1,3-4H2;/q-1;+1

InChI key

UPXWGXKSNOQOKH-UHFFFAOYSA-N

Application

Organotrifluoroborate involved in:
  • Catalytic allylboration[1]
  • Stereoselective nucleophilic addition[2]
  • Pd-catalyzed heterocyclizations[3]
  • Oxidation reactions[4] and Oxidative Mannich reactions[5]
  • Cross-coupling reactions[6]


Organotrifluoroborates as versatile and stable boronic acid surrogates

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKE122082

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Oxidation of alkyl trifluoroborates: an opportunity for tin-free radical chemistry.
Geoffroy Sorin et al.
Angewandte Chemie (International ed. in English), 49(46), 8721-8723 (2010-10-12)
The development of a Selectfluor-mediated oxidative Mannich reaction
M. H. Daniels and J. Hubbs,
Tetrahedron Letters, 52, 3543-3546 (2011)
Catalytic activation of pinacolyl allylboronate with indium(I): development of a general catalytic allylboration of ketones.
Uwe Schneider et al.
Angewandte Chemie (International ed. in English), 46(31), 5909-5912 (2007-06-20)
Michael J Burns et al.
Dalton transactions (Cambridge, England : 2003), 39(43), 10391-10400 (2010-10-15)
A new synthetic methodology for the catalytic C-H functionalisation of 2-pyrones is described which proceeds regioselectively at the C3 position, mirroring the observed regioselectivity in 6π-electrocyclisation/oxidative aromatisation reactions of related compounds. Insight into the reaction mechanism is provided, with support
A new organic transformation by introducing crotyl/allyltrifluoroborates in cross-coupling reaction with aroyl chlorides
M. Al-Masum and K. Liu,
Tetrahedron Letters, 52, 5090-5093 (2011)
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