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T84603

Sigma-Aldrich

Triphenylphosphine oxide

98%

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Synonym(s):
Ph3PO, TPPO, Triphenyl phosphorus oxide, 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

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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1 of 4

This Item
PHR25441478833261947
vibrant-m

T84603

Triphenylphosphine oxide

vibrant-m

PHR2544

Orlistat Related Compound C

vibrant-m

1478833

Orlistat Related Compound C

vibrant-m

261947

1,4-Bis(diphenylphosphino)butane

functional group

phosphine oxide

functional group

-

functional group

-

functional group

phosphine

assay

98%

assay

-

assay

-

assay

98%

reaction suitability

reagent type: ligand
reaction type: Coupling Reactions, reagent type: ligand
reaction type: Michael Reaction, reagent type: ligand
reaction type: Epoxidations

reaction suitability

-

reaction suitability

-

reaction suitability

reagent type: ligand
reaction type: Alkylations, reagent type: ligand
reaction type: Heck Reaction, reagent type: ligand
reaction type: Isomerizations, reagent type: ligand
reaction type: Negishi Coupling, reagent type: ligand
reaction type: Sonogashira Coupling, reagent type: ligand
reaction type: Stille Coupling, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

150-157 °C (lit.)

mp

150-157 °C (lit.)

mp

150-157 °C (lit.)

mp

132-136 °C (lit.)

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

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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Customers Also Viewed

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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)
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)
R Kyle Palmer et al.
Assay and drug development technologies, 8(6), 703-713 (2010-12-17)
Transient receptor potential melastatin-5 (TRPM5) is a calcium-gated monovalent cation channel expressed in highly specialized cells of the taste bud and gastrointestinal tract, as well as in pancreatic β-cells. Well established as a critical signaling protein for G protein-coupled receptor-mediated
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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