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Key Documents

92788

Sigma-Aldrich

(3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide

technical, ≥95% (NT)

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About This Item

Empirical Formula (Hill Notation):
C24H26BrPSi
CAS Number:
Molecular Weight:
453.43
Beilstein:
3581358
MDL number:
UNSPSC Code:
12352000

grade

technical

Assay

≥95% (NT)

mp

166-167 °C (dec.) (lit.)

SMILES string

[Br-].C[Si](C)(C)C#CC[P+](c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C24H26PSi.BrH/c1-26(2,3)21-13-20-25(22-14-7-4-8-15-22,23-16-9-5-10-17-23)24-18-11-6-12-19-24;/h4-12,14-19H,20H2,1-3H3;1H/q+1;/p-1

InChI key

PBSHVEOONSKWJF-UHFFFAOYSA-M

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Application

Reactant for:
  • Horner-Wadsworth-Emmons olefination
  • Aromatic ring umpolung
  • Stereoselective Wittig reaction
  • Bromoetherification reactions
  • Olefination of Garner′s aldehyde
  • Regioselective Wittig reaction

Other Notes

Wittig reagent for the synthesis of en-ynes; the (E)-olefin is formed preferentially

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R. Pontikis et al.
Canadian Journal of Chemistry, 67, 2240-2240 (1989)
E.J. Corey et al.
Tetrahedron Letters, 1495-1495 (1973)
Convergent, enantiospecific total synthesis of the hypocholesterolemic agent (+)-compactin.
P A Grieco et al.
Journal of the American Chemical Society, 108(19), 5908-5919 (1986-09-01)

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