Methyldiphenylphosphine

Base Information

• Chemical Name: Methyldiphenylphosphine
• CAS No.: 1486-28-8
• Molecular Formula: C13H13P
• Molecular Weight: 200.22
• Hs Code.: 29420000
• European Community (EC) Number: 216-065-5
• NSC Number: 158476
• UNII: RYN4FS3JEN
• DSSTox Substance ID: DTXSID30164028
• Nikkaji Number: J144.995H
• Wikipedia: Methyldiphenylphosphine
• Wikidata: Q72473379
• Mol file: 1486-28-8.mol

Synonyms:Methyldiphenylphosphine;1486-28-8;PHOSPHINE, METHYLDIPHENYL-;methyl(diphenyl)phosphane;Methyldiphenylphsphine;Diphenylmethylphosphine;METHYLDIPHENYLPHOSPHANE;C13H13P;RYN4FS3JEN;MFCD00008508;EINECS 216-065-5;NSC-158476;methyl(diphenyl)phosphine;Diphenylphosphinomethane;Diphenyl-methylphosphine;Phosphine,methyldiphenyl-;methyldiphenylphoshine;NSC158476;methyldi-phenylphosphine;P-methyldiphenylphosphine;UNII-RYN4FS3JEN;methyl-di(phenyl)phosphane;P(C)(c1ccccc1)c2ccccc2;SCHEMBL40441;Methyldiphenylphosphine, 99%;SCHEMBL12244769;UJNZOIKQAUQOCN-UHFFFAOYSA-;DTXSID30164028;AMY11734;C13-H13-P;AKOS015852460;CS-W015622;NSC 158476;SC11146;AS-58693;SY009856;FT-0625277;M1318;F17170;EN300-8664028;J-008496;1H,1H-2,5-Bis(trifluoromethyl)-3,6-dioxaperfluorononanol;DIPHENYLMETHYLPHOSPHINE;DIPHENYLPHOSPHINOMETHANE;METHYLDIPHENYLPHOSPHINE

Chemical Property of Methyldiphenylphosphine

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.00127mmHg at 25°C
• Melting Point: 117-118 °C
• Refractive Index: n20/D 1.625(lit.)
• Boiling Point: 308.1 °C at 760 mmHg
• Flash Point: 128.4 °C
• PSA: 13.59000
• Density: 1.076 g/mL at 25 °C(lit.)
• LogP: 2.74910
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Air Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 200.075487412
• Heavy Atom Count: 14
• Complexity: 137

Purity/Quality:

97% ^*data from raw suppliers

Methyldiphenylphosphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 17-23-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: CP(C1=CC=CC=C1)C2=CC=CC=C2
• General Description: Methyldiphenylphosphine (PPh2Me) is a monodentate phosphine ligand used in the synthesis of cycloplatinated(II) complexes, where it replaces dimethyl sulfoxide (DMSO) in [PtMe(Vpy)(DMSO)] to form [PtMe(Vpy)(PPh2Me)]. This complex exhibits intense phosphorescence emission in both solid state and solution, attributed to a mixed 3ILCT/3MLCT excited state, and undergoes oxidative addition reactions with alkyl halides via an SN2 mechanism, demonstrating its utility in optoelectronic and catalytic applications.

Technology Process of Methyldiphenylphosphine

There total 86 articles about Methyldiphenylphosphine 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%

diphenyl(methyl)phosphine oxide (2129-89-7) → diphenyl(methyl)phosphine (1486-28-8)

Guidance literature:

With lithium aluminium tetrahydride; cerium(III) chloride; In tetrahydrofuran; at 40 ℃; for 0.5h;

DOI:10.1246/cl.1985.1491

Reference yield: 96.0%

Diphenylphosphonigsaeure-trimethylsilylester (13683-01-7) + methyllithium (917-54-4) → diphenyl(methyl)phosphine (1486-28-8)

Guidance literature:

In tetrahydrofuran; at 0 - 25 ℃; for 2h;

DOI:10.1016/j.tetlet.2021.152870

Reference yield: 95.0%

Ph2PCH2NHPh + methyl iodide (74-88-4) → diphenyl(methyl)phosphine (1486-28-8)

Guidance literature:

Ph₂PCH₂NHPh; With methyllithium; In toluene; at -78 - 20 ℃; Inert atmosphere;

methyl iodide; In toluene; at -78 ℃; Inert atmosphere;

DOI:10.1016/j.jorganchem.2010.03.006

upstream raw materials:

diethyl ether

sodium methylate

chloro-diphenylphosphine

dimethyl zinc(II)

Downstream raw materials:

dimethyldiphenylphosphonium iodide

diphenyl(methyl)phosphine oxide

2,2-dihydro 2-methyl 2,2-diphenyl 3,4-methano 1,2-oxaphospholanne

1,8-bis(diphenylmethylphosphoranylideneammonio)naphthalene bromide

Refernces

Electron transfer-induced replacement of carbonyl ligands in cobalt clusters

10.1023/A:1015037008399

The study discusses a novel approach to replacing carbonyl ligands in cobalt clusters through the oxidation of an electroactive organometallic group linked to the cluster fragment via a conducting chain. The researchers used compounds with the electroactive group Cp*(dppe)Fe, which is connected to a Co2C2-type cluster by an acetylenide bridge. The purpose of these chemicals was to demonstrate the potential of this method as a model for molecular devices with a switch-on (oxidation) and switch-off (reduction) mechanism. The study involved the oxidation of compound I with Cp2FeBF4 to produce labile radical cations, which upon the addition of diphenylphosphinomethane (dppm), led to the replacement of carbonyl ligands and the formation of stable radical cations [2a,b]+. These cations were then reduced with Cp2Co to yield neutral diamagnetic compounds. The chemicals used served to facilitate these transformations and to characterize the resulting complexes through elemental analysis, IR spectroscopy, and NMR spectroscopy.

Cycloplatinated(II) complex bearing 2-vinylpyridine and monodentate phosphine ligands: Optical properties and kinetic study

10.1016/j.jorganchem.2015.12.005

The study focuses on the synthesis, characterization, and kinetic investigation of a cycloplatinated(II) complex bearing 2-vinylpyridine and monodentate phosphine ligands. The main chemical used was the 2-vinylpyridinate complex [PtMe(Vpy)(DMSO)], denoted as complex C, which was prepared from the dimeric platinum(II) complex cis,cis-[Me2Pt(m-SMe2)2PtMe2], known as complex B, in the presence of DMSO (dimethyl sulfoxide) and 2-vinylpyridine ligand. The DMSO molecule in complex C was substituted by methyldiphenylphosphine (PPh2Me) to synthesize [PtMe(Vpy)(PPh2Me)], referred to as complex 1. This complex was characterized by its optical properties, showing intense phosphorescence emission in solid state and solution, and was attributed to a mixed 3ILCT/3MLCT excited state. The study also investigated the oxidative addition reaction of complex 1 with alkyl halide (MeI), resulting in the formation of [PtMe2I(Vpy)(PPh2Me)], known as complex 2. Kinetic studies suggested that this reaction proceeded via a classical SN2 mechanism, and the rate of the reaction at different temperatures was measured, yielding a high negative DS# value that supported the proposed mechanism. The study serves to understand the reactivity of cycloplatinated complexes and their potential applications in fields such as optoelectronics and medicinal chemistry.