Triphenylphosphine oxide

Base Information

• Chemical Name: Triphenylphosphine oxide
• CAS No.: 791-28-6
• Deprecated CAS: 47027-44-1
• Molecular Formula: C18H15OP
• Molecular Weight: 278.29
• Hs Code.: 29310095
• European Community (EC) Number: 212-338-8
• NSC Number: 398
• UNII: Z69161FKI3
• DSSTox Substance ID: DTXSID2022121
• Nikkaji Number: J3.036.729D,J541J
• Wikipedia: Triphenylphosphine_oxide
• Wikidata: Q421154
• ChEMBL ID: CHEMBL482091
• Mol file: 791-28-6.mol

Synonyms:diphenylphosphine oxide;triphenylphosphine oxide

Chemical Property of Triphenylphosphine oxide

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 2.62E-08mmHg at 25°C
• Melting Point: 154-158 °C
• Refractive Index: 1.619
• Boiling Point: 462.9 °C at 760 mmHg
• Flash Point: 233.8 °C
• PSA: 26.88000
• Density: 1.17g/cm³
• LogP: 3.32600
• Storage Temp.: Store at RT.
• Solubility.: methanol: 25 mg/mL, clear
• Water Solubility.: slightly soluble
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 278.086052095
• Heavy Atom Count: 20
• Complexity: 281

Purity/Quality:

99% ^*data from raw suppliers

Triphenylphosphine oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-52/53
• Safety Statements: 26-61-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3
• 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.
• Uses: Triphenylphosphine oxide is a phosphine ligand used for coupling reactions, epoxidations, and Michael reactions 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. 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.

Technology Process of Triphenylphosphine oxide

There total 2287 articles about Triphenylphosphine oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

2,2'-dipyridyldisulphide (2127-03-9) + 2,4-dimethylbenzenesulfonic acid (88-61-9) + triphenylphosphine (603-35-0) → 2-Sulfanylpyridine (2637-34-5,73018-10-7) + 2,4-dimethyl-thiophenol (13616-82-5) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

In benzene; for 2h; Product distribution; Mechanism; Heating; further reaction partners - various diaryl disulfides;

DOI:10.1246/bcsj.57.232

Reference yield: 89.0%

benzamide (55-21-0,27208-38-4) + triphenylphosphine (603-35-0) → benzonitrile (100-47-0) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With aluminum oxide; LutClO₄; In dichloromethane; constant current electrolysis;

Reference yield: 86.0%

p-nitrophenyl-N-(p-toluenesulfonyl)sulfinimidoyl chloride (5184-32-7) + triphenylphosphine (603-35-0) → di(p-nitrophenyl) disulfide (100-32-3) + Triphenylphosphine oxide (791-28-6) + N-p-tolylsulfonylphosphine imide (1058-14-6)

Guidance literature:

p-nitrophenyl-N-(p-toluenesulfonyl)sulfinimidoyl chloride; triphenylphosphine; In benzene; at 20 ℃; for 0.5h;

With water; In benzene; for 5h; Further stages.;

DOI:10.1002/hc.20408

upstream raw materials:

diethyl ether

phosphoric acid triphenyl ester

ethanol

diphenyldiazomethane triphenylphosphazine

Downstream raw materials:

(3-benzyl-phenyl)-diphenyl-phosphine oxide

tetraphenyl phosphonium chloride

diphenyl-phosphinic acid

triphenylphosphine

Refernces

Dual [Fe+Phosphine] catalysis: Application in catalytic wittig olefination

10.1002/cctc.201500053

The study presented in the PDF document titled "Dual [Fe+Phosphine] Catalysis: Application in Catalytic Wittig Olefination" focuses on the development and application of a dual catalysis system involving iron hydride complexes and phosphines for the selective reduction of carbonyl and phosphine oxide groups. The researchers explored the use of Fe-based complexes for the hydrosilylation of aldehydes, ketones, and phosphine oxides, demonstrating that these complexes could effectively reduce phosphine oxides to phosphines. This reduction process was then integrated into a catalytic Wittig olefination reaction, which is a synthetically useful transformation for the formation of olefins from aldehydes or ketones and a-halocarboxylic acid esters. The study successfully utilized a readily accessible Fe-H complex in conjunction with triphenylphosphine as an organocatalyst and phenylsilane as a stoichiometric reductant, achieving moderate to good yields of the desired olefination products. This work not only expands the application scope of Fe-based catalysis but also provides a potential avenue for the in situ recycling of phosphines, which is beneficial for large-scale applications and more sustainable chemical processes.