Trimethylphosphine oxide

Base Information

• Chemical Name: Trimethylphosphine oxide
• CAS No.: 676-96-0
• Molecular Formula: C3H9OP
• Molecular Weight: 92.0776
• Hs Code.: 29319090
• European Community (EC) Number: 211-633-9
• UNII: 4M39GK79DV
• DSSTox Substance ID: DTXSID90217923
• Nikkaji Number: J1.191.948K,J536C
• Wikidata: Q69756952
• Mol file: 676-96-0.mol

Synonyms:trimethylphosphine oxide

Chemical Property of Trimethylphosphine oxide

Chemical Property:

• Appearance/Colour: colorless crystals
• Vapor Pressure: 0.64mmHg at 25°C
• Melting Point: 140-141°C
• Refractive Index: 1.364
• Boiling Point: 193.7 °C at 760 mmHg
• Flash Point: 71 °C
• PSA: 26.88000
• Density: 0.9 g/cm³
• LogP: 1.23890
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Soluble in polar organic solvents.
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 92.039101904
• Heavy Atom Count: 5
• Complexity: 53

Purity/Quality:

99% ^*data from raw suppliers

Trimethylphosphine oxide 98% ^*data from reagent suppliers

Safty Information:

• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CP(=O)(C)C
• Uses: Trimethylphosphine oxide is a common side product in organic synthesis, including the Wittig, Staudinger, Mitsunobu reactions and also in the manufacture of triphenylphosphine. It is a popular reagent to induce the crystallization of various chemical compounds. It acts as an excellent ligand for hard metal centers. It can react with 9-methyl-9-azonianthracene methyl sulfate to get (10-methyl-9,10-dihydro-acridin-9-yl)-phosphonic acid dimethyl ester using sodium iodide and acetonitrile as solvent.

Technology Process of Trimethylphosphine oxide

There total 69 articles about Trimethylphosphine 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: 95.0%

methylmagnesium chloride (676-58-4) → Trimethylphosphine oxide (676-96-0)

Guidance literature:

With copper dichloride; trichlorophosphate; In tetrahydrofuran; toluene; at 5 ℃; for 2h; Temperature; Solvent; Reagent/catalyst;

Reference yield: 95.0%

dimethyl methane phosphonate (756-79-6) → methane (34557-54-5,27936-85-2) + Trimethylphosphine oxide (676-96-0) + Dimethyl ether (115-10-6,157621-61-9) + magnesium bis(methyl methylphosphonate)

Guidance literature:

With magnesium; In neat (no solvent); at 165 ℃; for 1.5h; Further byproducts given;

Reference yield: 94.0%

methyl iodide (74-88-4) → Trimethylphosphine oxide (676-96-0)

Guidance literature:

methyl iodide; With magnesium; In diethyl ether; Reflux; Schlenk technique;

With trichlorophosphate; In diethyl ether; Reflux; Schlenk technique; Cooling with ice;

DOI:10.1002/anie.201811032

upstream raw materials:

tetramethylphosphonium hydroxide

trimethylphosphane

dimethyl methane phosphonate

methyl iodide

Downstream raw materials:

(C₅H₅)Ti(NHC₆H₃(CH₃)2)(NC₆H₃(CH₃)2)(OP(CH₃)3)