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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:
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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3

Storage Class Code

11 - Combustible Solids

WGK

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

Phosphine oxide-catalysed chlorination reactions of alcohols under Appel conditions
Denton RM, et al.
Chemical Communications (Cambridge, England), 46(17), 3025-3027 (2010)
Triphenylphosphine oxide-catalyzed stereoselective poly-and dibromination of unsaturated compounds
Yu T, et al.
Chemical Communications (Cambridge, England), 50(58), 7817-7820 (2014)
?-Selective Ribofuranosylation of Alcohols with Ribofuranosyl Iodides and Triphenylphosphine Oxide
Oka N, et al.
The Journal of Organic Chemistry, 79(16), 7656-7664 (2014)
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...
Steven Kealey et al.
Dalton transactions (Cambridge, England : 2003), (42)(42), 4763-4765 (2007-10-24)
A new tetrakis(pyrazolyl)borate ligand bearing triphenylphosphine oxide moieties appended to the 3-position of the pyrazolyl rings is reported and shown to display varied coordination chemistry from tridentate N(2)O coordination with thallium to hexadentate N(3)O(3) coordination with europium.

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