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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:
791-28-6
Peso molecular:
278.28
Beilstein/REAXYS Number:
745854
EC Number:
212-338-8
MDL number:
MFCD00002080
UNSPSC Code:
12352002
PubChem Substance ID:
24900532
NACRES:
NA.22

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
GHS07

signalword

Warning

hcodes

H302,H412

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

Certificados de análisis (COA)

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Triphenylphosphine oxide-catalyzed stereoselective poly-and dibromination of unsaturated compounds
Yu T, et al.
Chemical Communications (Cambridge, England), 50(58), 7817-7820 (2014)
Phosphine oxide-catalysed chlorination reactions of alcohols under Appel conditions
Denton RM, et al.
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)
Stephen M Richoll et al.
Journal of chromatography. A, 1127(1-2), 147-153 (2006-07-04)
A versatile procedure has been developed and validated for the determination of triphenylphosphine oxide (TPPO) at low levels in various active pharmaceutical ingredients (APIs). This procedure incorporates the use of the novel hollow-fiber liquid-phase microextraction (LPME) for the measurement of
S Takeda et al.
Anticancer research, 13(1), 193-199 (1993-01-01)
We have investigated the nature of lipid peroxidation occurring in association with cancer-killing produced by gamma-linolenic acid (GLA) and iron (Fe) in cultured human breast cancer cells (ZR-75-1: ZR). UV-spectrophotometry, high performance liquid chromatography (HPLC) and gas chromatography (GC) or
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