CAS 791-28-6 Triphenylphosphine oxide - Catalysts / Alfa Chemistry

Synonyms

Phosphine oxide, triphenyl-; Triphenyl phosphorus oxide; (C6H5)3P=O; Triphenylphosphanoxid; Triphenylphosphanoxide; (C6H5)3PO;Triphenylphosphine oxide;Triphenyl phosphorus oxide

IUPAC Name

diphenylphosphorylbenzene

Molecular Weight

278.28

Molecular Formula

C18H15OP

Canonical SMILES

C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3;

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

Boiling Point

360 °C

Melting Point

150-157 °C(lit.)

Flash Point

180 °C

Purity

99%

Density

1.212 g/cm3

Appearance

Solid

Storage

Store at RT.

Complexity

281

Covalently-Bonded Unit Count

EC Number

212-338-8

Exact Mass

278.086g/mol

H-Bond Acceptor

Heavy Atom Count

Isomeric SMILES

C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3

Monoisotopic Mass

278.086g/mol

NSC Number

398

Physical State

Solid

Rotatable Bond Count

Topological Polar Surface Area

17.1A^2

UNII

Z69161FKI3

Vapor Pressure

2.60e-09 mmHg;

Application

Triphenylphosphine oxide serves a multifaceted purpose in chemical processes, primarily as a coordinating solvent that facilitates the crystallization of various compounds. Its applications extend beyond crystallization, as it plays a crucial role as a catalyst in numerous chemical reactions, including Appel-type chlorination of alcohols and stereoselective poly and dibromination of unsaturated esters. It also acts as a promotor in the diastereoselective synthesis of α-ribofuranosides and assists in transforming aldehydes into 1,1-dichlorides. Additionally, Triphenylphosphine oxide is employed in producing highly functionalized α-CF3 γ-keto esters and finds use as both a ligand for coupling reactions, epoxidations, and more. Moreover, its utility extends to flame retardant applications and as an epoxy cure catalyst, with recent innovations leveraging it for nanostructure production.

February 13, 2025

Excellent Catalyst for Research Applications

Using Triphenylphosphine oxide as a catalyst significantly improved our stereoselective bromination processes. It's effective and easy to handle in lab-scale crystallization, proving indispensable in our recent projects on α-CF3 γ-keto ester synthesis.