Diphenylphosphine

Base Information

• Chemical Name: Diphenylphosphine
• CAS No.: 829-85-6
• Molecular Formula: C12H11P
• Molecular Weight: 186.193
• Hs Code.: 29319090
• European Community (EC) Number: 212-591-4
• NSC Number: 152123
• UNII: F9B5T7O7ZY
• DSSTox Substance ID: DTXSID50232076
• Nikkaji Number: J99.507J
• Wikipedia: Diphenylphosphine
• Wikidata: Q413810
• Mol file: 829-85-6.mol

Synonyms:Diphenylphosphine;829-85-6;diphenylphosphane;Phosphine, diphenyl-;PH2PH;UNII-F9B5T7O7ZY;F9B5T7O7ZY;C12H11P;EINECS 212-591-4;MFCD00003040;NSC-152123;Diphenylphosphine,99%(10Wt%Inhexane);diphenylphospine;diphenyl-phosphane;Diphenyl phosphine;diphenyl-Phosphine;(diphenyl)phosphine;NSC152123;HPPH2;Diphenylphosphine, 98%;SCHEMBL49343;DIPHENYLPHOSPHINE [MI];SCHEMBL7779011;GPAYUJZHTULNBE-UHFFFAOYSA-;DTXSID50232076;AMY39375;BCP22575;C12-H11-P;AKOS015840617;GC10090;NSC 152123;D1020;FT-0625280;Diphenylphosphine, 99% (10 wt% in hexanes);EN300-8107138;Q413810;DIPHENYLPHOSPHANE;DIPHENYLPHOSPHINE;PHOSPHINE,DIPHENYL

Chemical Property of Diphenylphosphine

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 2 mm Hg ( 110 °C)
• Melting Point: 65-67oC (338-340 K)
• Refractive Index: n20/D 1.625(lit.)
• Boiling Point: 275 °C at 760 mmHg
• PKA: diphenylphosphine is weakly basic. The pKa of the protonated derivative is 0.03.
• Flash Point: 120.1 °C
• PSA: 13.59000
• Density: 1.07 g/cm³
• LogP: 2.31590
• Storage Temp.: 2-8°C
• Sensitive.: Air & Moisture Sensitive
• Solubility.: Chloroform
• Water Solubility.: Miscible with ethanol, ether, benzene, concentrated hydrochloric acid. Immiscible with water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 186.059837349
• Heavy Atom Count: 13
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

Diphenylphosphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 17-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: C1=CC=C(C=C1)PC2=CC=CC=C2
• Uses: It can be used the intermediates of organic, catalysts. suzuki reaction Diphenylphosphine is used in the synthesis of aminophosphines for application as catalysts. It is also used in the preparation of chiral palladacycles with N-heterocyclic carbene ligands as catalysts. Diphenylphosphine acts as an intermediate in the preparation of diphenylphosphide derivatives, phosphonium salts, phosphine ligands and Wittig-Horner reagents. The presence of hydrogen atom bonded to phosphorus undergoes Michael-like addition to activated alkenes. It is involved in the preparation of 1,2-bis(diphenylphosphino)ethane and (phenyl-(phenylmethyl)phosphoryl)benzene. Further, it is used in the synthesis of aminophosphines and chiral palladacycles with N-heterocyclic carbene ligands as catalysts.

Technology Process of Diphenylphosphine

There total 138 articles about Diphenylphosphine 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: 80.0%

bromobenzene (108-86-1,52753-63-6) → triphenylphosphine (603-35-0) + diphenylphosphane (829-85-6) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With phosphorous; Ni⁽⁰⁾bipy; In N,N-dimethyl-formamide; Electrochemical reaction; Zn anode;

DOI:10.1016/j.jorganchem.2004.11.008

Reference yield: 75.0%

iodobenzene (591-50-4) → triphenylphosphine (603-35-0) + phenylphosphane (638-21-1) + diphenylphosphane (829-85-6)

Guidance literature:

With phosphorous; Ni⁽⁰⁾bipy; In N,N-dimethyl-formamide; Electrochemical reaction; Zn anode;

DOI:10.1016/j.jorganchem.2004.11.008

Reference yield: 69.0%

Triphenylphosphine oxide (791-28-6) → triphenylphosphine (603-35-0) + Diphenylphosphine oxide (4559-70-0) + diphenylphosphane (829-85-6)

Guidance literature:

Triphenylphosphine oxide; With chloro-trimethyl-silane; tetrabutylammomium bromide; platinum; 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:

phenyl diphenylphosphinite

chloro-diphenylphosphine

Diphenylphosphinic chloride

diphenylisothiocyanatophosphine

Downstream raw materials:

Tetraphenyldiphosphin

2-(diphenylphosphinyl)ethanol

ethyl (diphenylphosphino)acetate

diphenylphosphinoacetic acid

Refernces

• 1、 Ushakov, N. V.,Vdovin, V. M.,Pozdnyakova, M. V.,Pritula, N. A.. "REACTION OF LITHIUM DIPHENYLPHOSPHIDE WITH MONOSILACYCLOBUTANES". . p. 1920 - 1923. Retrieved 1983.
• 2、 Cammarata, Jose,Gschwind, Ruth M.,Lennert, Ulrich,Rothfelder, Robin,Scott, Daniel J.,Streitferdt, Verena,Wolf, Robert,Zeitler, Kirsten. "Photocatalytic Arylation of P4 and PH3: Reaction Development Through Mechanistic Insight". supporting information. p. 24650 - 24658. Retrieved 2021/10/14.
• 3、 Gasperini, Danila,Neale, Samuel E.,Mahon, Mary F.,MacGregor, Stuart A.,Webster, Ruth L.. "Phosphirenium ions as masked phosphenium Catalysts: Mechanistic evaluation and application in synthesis". . p. 5452 - 5462. Retrieved 2021/06/01.