Diphenylphosphine oxide

Base Information

• Chemical Name: Diphenylphosphine oxide
• CAS No.: 4559-70-0
• Molecular Formula: C12H11OP
• Molecular Weight: 202.193
• Hs Code.: 29319090
• European Community (EC) Number: 625-671-2
• NSC Number: 77604
• UNII: XXW49HG6X3
• DSSTox Substance ID: DTXSID60422562
• Wikipedia: Diphenylphosphine_oxide
• Wikidata: Q72473451,Q106902862
• Mol file: 4559-70-0.mol

Synonyms:NSC 77604;

Chemical Property of Diphenylphosphine oxide

Chemical Property:

• Appearance/Colour: Yellow to light orange crystals
• Melting Point: 56-57 °C(lit.)
• Refractive Index: 1.608-1.61
• Boiling Point: 329.217 °C at 760 mmHg
• Flash Point: 152.905 °C
• PSA: 40.54000
• LogP: 2.19710
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Moisture Sensitive
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 201.046926936
• Heavy Atom Count: 14
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

Diphenylphosphine oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[P+](=O)C2=CC=CC=C2
• General Description: Diphenylphosphine oxide (also known as NSC 77604) is a key phosphorus source used in the synthesis of water-soluble tertiary phosphine oxides via Pd/C-catalyzed P-C coupling in water. Diphenylphosphine oxide serves as a precursor in an environmentally friendly and efficient method for carbon-phosphorus bond formation, enabling the production of phosphine derivatives with high yields and purity. The resulting water-soluble phosphine oxides are advantageous for industrial applications involving homogeneous catalysis, as the process eliminates the need for organic solvents and is both recyclable and scalable.

Technology Process of Diphenylphosphine oxide

There total 112 articles about Diphenylphosphine 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: 98.0%

1-(diphenylphosphinoyl)-1,1-dimethoxy-3-butene → methyl but-3-enoate (3724-55-8) + Diphenylphosphine oxide (4559-70-0)

Guidance literature:

With hydrogenchloride; In dichloromethane;

DOI:10.1002/ejoc.200300631

Reference yield: 94.0%

1-(diphenylphosphinoyl)-1,1-dimethoxy-2-phenylethane → Diphenylphosphine oxide (4559-70-0) + benzeneacetic acid methyl ester (101-41-7)

Guidance literature:

With hydrogenchloride; In dichloromethane;

DOI:10.1002/ejoc.200300631

Reference yield: 89.0%

Triphenylphosphine oxide (791-28-6) → triphenylphosphine (603-35-0) + Diphenylphosphine oxide (4559-70-0)

Guidance literature:

Triphenylphosphine oxide; With chloro-trimethyl-silane; tetrabutylammomium bromide; copper; zinc; In acetonitrile; at 45 ℃; for 2.15h; Electrochemical reaction; Inert atmosphere;

With hydrogenchloride; In water; acetonitrile; Inert atmosphere;

DOI:10.1055/s-0031-1289612

upstream raw materials:

chloro-diphenylphosphine

phosphonic acid diethyl ester

diphenyl-phosphinic acid

P,P'-tetraphenyl-oxalic acid diphosphide

Downstream raw materials:

Diphenylphosphinic chloride

N-phenyl(diphenylphosphinoyl)formamide

1-(diphenylphosphoryl)-N-phenylmethanethioamide

(dimethylamino)(diphenylphosphinoyl)methoxymethane

Refernces

Synthesis of water-soluble phosphine oxides by Pd/C-catalyzed P-C coupling in water

10.1021/ol300582y

This research presents a green, simple, and fast protocol for synthesizing water-soluble tertiary phosphine oxides through Pd/C-catalyzed P-C coupling in water. The purpose is to develop an environmentally friendly and sustainable method for carbon-phosphorus coupling that produces water-soluble phosphine derivatives, which have advantages in industrial processes based on homogeneous catalysts. Key chemicals used include diphenylphosphine oxide as the P-source, halogenated benzoic acids as coupling partners, and Pd/C as the catalyst. The reaction is performed in water, with microwave irradiation and K2CO3 as the base. The method allows for the synthesis of several new phosphine oxides with high yields and purity, without the need for organic solvents in reactions and workup. The protocol is also recyclable and scalable, making it a promising candidate for both laboratory and large-scale synthesis.