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T84603

Sigma-Aldrich

Triphenylphosphine oxide

98%

Synonym(s):

Ph3PO, TPPO, Triphenyl phosphorus oxide, Triphenylphosphine monoxide

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About This Item

Linear Formula:
(C6H5)3PO
CAS Number:
791-28-6
Molecular Weight:
278.28
Beilstein:
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

Signal Word

Warning

Hazard Statements

H302,H412

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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?-Selective Ribofuranosylation of Alcohols with Ribofuranosyl Iodides and Triphenylphosphine Oxide
Oka N, et al.
The Journal of Organic Chemistry, 79(16), 7656-7664 (2014)
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)
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
Richard J Emery et al.
Environment international, 31(2), 207-211 (2005-01-22)
The degradation of triphenylphosphine oxide (TPPO) in water, a toxic compound typically found in effluents from the pharmaceutical industry, by means of ultrasonic irradiation at 20 kHz has been investigated with emphasis on the effect of various parameters on conversion
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