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MilliporeSigma

T84603

Sigma-Aldrich

Triphenylphosphine oxide

98%

Sinónimos:

Ph3PO, TPPO, Triphenyl phosphorus oxide, Triphenylphosphine monoxide

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About This Item

Fórmula lineal:
(C6H5)3PO
Número de CAS:
Peso molecular:
278.28
Beilstein/REAXYS Number:
745854
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

reaction suitability

reagent type: ligand
reaction type: Coupling Reactions

reagent type: ligand
reaction type: Epoxidations

reagent type: ligand
reaction type: Michael Reaction

mp

150-157 °C (lit.)

functional group

phosphine oxide

SMILES string

O=P(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C18H15OP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

InChI key

FIQMHBFVRAXMOP-UHFFFAOYSA-N

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Application

Triphenylphosphine oxide can be used:
  • As a catalyst in Appel-type chlorination reaction of acyclic primary and secondary alcohols.
  • As a catalyst in stereoselective poly and dibromination of α,β-unsaturated esters and β,γ-unsaturated α-ketoester compounds.
  • As a promotor in the diastereoselective synthesis of α-ribofuranosides through ribofuranosylation of alcohols with ribofuranosyl iodides.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

356.0 °F

flash_point_c

180 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Phosphine oxide-catalysed chlorination reactions of alcohols under Appel conditions
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Chemical Communications (Cambridge, England), 46(17), 3025-3027 (2010)
B H Lipshutz et al.
Organic letters, 3(12), 1869-1871 (2001-06-19)
[see reaction]. A simple, highly effective method for removing triphenylphosphine and/or triphenylphosphine oxide from reaction mixtures is described. Commercially available high-loading chloromethylated polystyrene 1, modified in situ with NaI, acts as a scavenger resin. Several coupling reactions catalyzed by Pd(0)
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