Methyl(phenyl)phosphine oxide

Base Information

• Chemical Name: Methyl(phenyl)phosphine oxide
• CAS No.: 19315-13-0
• Molecular Formula: C₇H₉OP
• Molecular Weight: 140.122
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID60544339
• Wikidata: Q82421432
• Mol file: 19315-13-0.mol

Synonyms:Methyl(phenyl)phosphine oxide;19315-13-0;methyl-oxo-phenylphosphanium;Phosphine oxide, methylphenyl-;methylphenylphosphine oxide;Methyl(oxo)phenylphosphanium;SCHEMBL2154648;(METHYLPHOSPHOROSO)BENZENE;DTXSID60544339;AKOS016003197;O11981

Chemical Property of Methyl(phenyl)phosphine oxide

Chemical Property:

• Vapor Pressure: 0.152mmHg at 25°C
• Boiling Point: 222.374oC at 760 mmHg
• Flash Point: 88.289oC
• PSA: 40.54000
• LogP: 1.50140
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 139.031276872
• Heavy Atom Count: 9
• Complexity: 106

Purity/Quality:

97% ^*data from raw suppliers

METHYL(PHENYL)PHOSPHINE OXIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[P+](=O)C1=CC=CC=C1

Technology Process of Methyl(phenyl)phosphine oxide

There total 42 articles about Methyl(phenyl)phosphine 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: 93.0%

methyllithium (917-54-4) + (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl phenylphosphinate (31352-60-0,31352-61-1,54353-18-3) → (Sp)-methyl(phenylphosphine oxide) (891848-03-6,102222-19-5,102222-20-8,19315-13-0)

Guidance literature:

In diethyl ether; at -80 - 0 ℃; for 1h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ja804412k

Reference yield: 93.0%

(Sp)-O-(+)-menthyl-H-phosphinate (172823-06-2) + methylmagnesium bromide (75-16-1) → (Sp)-methyl(phenylphosphine oxide) (891848-03-6,102222-19-5,102222-20-8,19315-13-0)

Guidance literature:

In diethyl ether; at -80 ℃; for 4h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ja804412k

Reference yield: 92.0%

(-)-menthyl phenylphosphinate (1164367-99-0) + methyllithium (917-54-4) → (Sp)-methyl(phenylphosphine oxide) (891848-03-6,102222-19-5,102222-20-8,19315-13-0)

Guidance literature:

(-)-menthyl phenylphosphinate; methyllithium; In diethyl ether; pentane; at -80 - 0 ℃;

With water; In diethyl ether; pentane; at -80 ℃;

upstream raw materials:

Methyl(phenyl)cyanphosphan

methylphenylphosphine

ethyl Phenylphosphinate

methylmagnesium chloride

Downstream raw materials:

trans-1-(methylphenylphosphinyl)-2-(diphenylphosphinyl)ethene

C₁₆H₂₀O₂P₂

(S,S)-1,2-Ethanediylbis(methylphenylphosphine oxide)

meso-(E)-ethene-1,2-diylbis[methyl(phenyl)phosphane] dioxide

Refernces

Reduction of functionalized tertiary phosphine oxides with BH₃

10.1021/jo502623g

The study presents a novel and efficient method for the reduction of tertiary hydroxyalkylphosphine oxides to the corresponding tertiary hydroxyalkylphosphine-boranes using borane (BH3) as a mild reducing agent. This direct and stereoselective conversion is facilitated by the presence of an α- or β-hydroxy group in the phosphine oxide structure, which enables an intramolecular P≡O···B complexation. The study demonstrates that the reduction of the P≡O bond occurs with complete inversion of configuration at the phosphorus center. The method's mild conditions and high yields make it a valuable approach for the synthesis of organophosphorus compounds, particularly those that are functionalized and/or nonracemic. The research also includes the exploration of the stereochemical course of the reduction and the role of the hydroxyl group in the reduction process, providing insights into the mechanism and potential applications in organic chemistry.