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Triphenylphosphine oxide
PRICE INQUIRYCatalog Number
ACM791286-2
Product Name
Triphenylphosphine oxide
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/791-28-6.gif)
CAS
791-28-6
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
1
EC Number
212-338-8
Exact Mass
278.086g/mol
H-Bond Acceptor
1
Heavy Atom Count
20
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
3
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.
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