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
• Uses: suzuki reaction Used in the preparation of triarylphosphine oxides, and as asymmetric catalysts, preparation of alkenyldiphenylphosphine oxides, and Horner-Wittig reagents. It is a ligand for Buchwald-Hartwig Cross Coupling Reaction, Hydrophosphonylations and Suzuki-Miyaura Coupling.

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:

(dimethylamino)(diphenylphosphinoyl)methoxymethane

1,2-Bis(diphenylphosphinyl)ethylidenimin

diphenyl(acetyl)phosphine oxide

1-Diphenylphosphinoyl-1-diphenylphosphinoyloxyaethan

Refernces

• 1、 Storch,Siebert,Rominger,Trapp. "5,5'-Diamino-BIPHEP ligands bearing small selector units for non-covalent binding of chiral analytes in solution". . p. 15665 - 15668. Retrieved 2015.
• 2、 Shioji, Kosei,Matsumoto, Akio,Takao, Masahiko,Kurauchi, Yoshimitsu,Shigetomi, Toshiyuki,Yokomori, Yoshinobu,Okuma, Kentaro. "Cycloadditions of 3,4-dihydro-2H-pyrrole N-oxide with thioketones and a selenoketone". . p. 743 - 746. Retrieved 2007.
• 3、 Zhang, Jian-Qiu,Zhao, Jingzhuo,Li, Chunya,Ye, Jingjing,Han, Li-Biao. "Conversion of α‐hydroxy(2,4,6‐trimethylbenzyl)diphenylphosphine oxide to TPO: oxidation vs decomposition". . p. 207 - 210. Retrieved 2020.
• 4、 Alexandrova, Elena А.,Lotsman, Kristina А.,Lyssenko, Konstantin А.,Trishin, Yuri G.. "Synthesis of novel N,O-macrocyclic ligands, functionalized by phosphine oxide groups". . p. 875 - 881. Retrieved 2019.
• 5、 Trishin,Kudryavtseva,Shafeeva,Avdeeva,Karpova. "First example of phosphorylation of macrocyclic azomethine with secondary phosphine oxides". . p. 2345 - 2346. Retrieved 2013.
• 6、 Ling, Liang,Luo, Meiming,Tang, Jinghua,Yuan, Shuqing,Zeng, Xiaoming. "Catalytic Cleavage of Unactivated C(aryl)-P Bonds by Chromium". supporting information. p. 1581 - 1586. Retrieved 2022/03/14.
• 7、 Yi, Ming-Jun,Xiao, Teng-Fei,Li, Wen-Hui,Zhang, Yi-Fan,Yan, Pen-Ji,Zhang, Baoxin,Xu, Peng-Fei,Xu, Guo-Qiang. "Organic photoredox catalytic α-C(sp3)-H phosphorylation of saturated: Aza -heterocycles". supporting information. p. 13158 - 13161. Retrieved 2021/12/16.