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15575

Sigma-Aldrich

9-Borabicyclo[3.3.1]nonyl trifluoromethanesulfonate solution

purum, ~0.5 M in hexane

Synonym(s):

9-BBN triflate solution, 9-BBN·CF3SO3, 9-[[(Trifluoromethyl)sulfonyl]oxy]-9-borabicyclo[3.3.1]nonane

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About This Item

Empirical Formula (Hill Notation):
C9H14BF3O3S
CAS Number:
62731-43-5
Molecular Weight:
270.08
Beilstein:
995656
MDL number:
MFCD00167981
UNSPSC Code:
12352000
PubChem Substance ID:
24849562
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grade

purum

reaction suitability

reagent type: reductant

concentration

~0.5 M in hexane

SMILES string

FC(F)(F)S(=O)(=O)OB1C2CCCC1CCC2

InChI

1S/C9H14BF3O3S/c11-9(12,13)17(14,15)16-10-7-3-1-4-8(10)6-2-5-7/h7-8H,1-6H2/t7-,8+

InChI key

NXHUKDCGEGEZCX-OCAPTIKFSA-N

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Application

Reactant for:
  • Preparation of a dialkylborenium ion stabilized by an N-heterocyclic carbene
  • Mukaiyama aldol addition
  • Preparation of porphyrin dimethyldioxanyl tolyl derivative complex
  • Preparation of palladium porphyrin complexes
  • Boron-mediated β-alkoxy Me ketone aldol addition reactions

  • Enolization agent

Other Notes

Reagent used for the formation of enol borinates from carbonyl compounds employed in stereoselective aldol reactions[1][2][3]

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Journal of the American Chemical Society, 103, 1568-1568 (1981)
S. Massamune et al.
Journal of the American Chemical Society, 103, 1566-1566 (1981)
T. Inoue et al.
Bulletin of the Chemical Society of Japan, 53, 174-174 (1980)

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