Triphenylphosphine oxide

Description

Triphenylphosphine oxide (TPPO) is a coordinating solvent used to activate crystallization of chemical compounds. It has been used in flame retardant applications, as an epoxy cure catalyst, and more recently, to produce nanostructures.

Chemical properties

White solid

The Uses of Triphenylphosphine oxide

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.

The Uses of Triphenylphosphine oxide

Triphenylphosphine oxide is a phosphine ligand used for coupling reactions, epoxidations, and Michael reactions

The Uses of Triphenylphosphine oxide

Triphenylphosphine Oxide (Orlistat USP Related Compound C) is a catalyst in the conversion of aldehydes into 1,1-dichlorides. Triphenylphosphine Oxide is used as a catalyst for the synthesis of hightly functionalized α-CF3 γ-keto esters.

Definition

ChEBI: A phosphine oxide in which the substituents on phosphorus are three phenyl groups.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 5463, 1990 DOI: 10.1016/S0040-4039(00)97873-0

Flammability and Explosibility

Not classified

Structure

Triphenylphosphine oxide is structurally related to POCl3. As established by X-ray crystallography, the geometry around P is tetrahedral, and the P-O distance is 1.48 ?. Other modifications of Ph3PO have been found: For example, a monoclinic form crystalizes in the space group P21/c with Z = 4 and a = 15.066 ?, b = 9.037 ?, c = 11.296 ?, and β = 98.47°.The orthorhombic modification crystallizes in the space group Pbca with Z = 4 and 29.089 ?, b = 9.1347 , c = 11.261(1) ?.

Purification Methods

It crystallises from absolute EtOH and is dried in vacuo. The gold chloride complex has m 177.5-178.5o. [Addison & Sheldon J Chem Soc 2705 1956, Cox & Westheimer J Am Chem Soc 80 5441 1958, Beilstein 16 III 864, 16 1011.]