T84603

Sigma-Aldrich

Triphenylphosphine oxide

98%

Synonym(s):
TPPO, Triphenyl phosphorus oxide, Ph3PO, Triphenylphosphine monoxide
Linear Formula:
(C6H5)3PO
CAS Number:
Molecular Weight:
278.28
Beilstein/REAXYS Number:
745854
EC Number:
MDL number:
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

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.

Packaging

25, 100 g in poly bottle

pictograms

Exclamation mark

signalword

Warning

hazcat

Acute Tox. 4 Oral - Aquatic Chronic 3

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 2

Flash Point F

356.0 °F

Flash Point C

180 °C

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Li Na Quan et al.
Nature communications, 11(1), 170-170 (2020-01-12)
Reduced-dimensional perovskites are attractive light-emitting materials due to their efficient luminescence, color purity, tunable bandgap, and structural diversity. A major limitation in perovskite light-emitting diodes is their limited operational stability. Here we demonstrate that rapid photodegradation arises from edge-initiated photooxidation...
Phosphine oxide-catalysed chlorination reactions of alcohols under Appel conditions
Denton RM, et al.
Chemical Communications (Cambridge, England), 46(17), 3025-3027 (2010)
Ya-Kun Wang et al.
Nature communications, 11(1), 3674-3674 (2020-07-24)
Metal halide perovskites have emerged as promising candidates for solution-processed blue light-emitting diodes (LEDs). However, halide phase segregation - and the resultant spectral shift - at LED operating voltages hinders their application. Here we report true-blue LEDs employing quasi-two-dimensional cesium...
?-Selective Ribofuranosylation of Alcohols with Ribofuranosyl Iodides and Triphenylphosphine Oxide
Oka N, et al.
The Journal of Organic Chemistry, 79(16), 7656-7664 (2014)
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...

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