13468-89-8

Basic information

• Product Name: 2-phenyl-1,3,2-dioxaphospholane 2-oxide
• CAS NO: 13468-89-8
• Molecular Formula: C₈H₉O₃P
• Molecular Weight: 184.129
• Mol File: 13468-89-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 269°C at 760 mmHg
• Flash Point: 130.5°C
• Density: 1.28g/cm³
• Vapor Pressure: 0.0123mmHg at 25°C
• Refractive Index: 1.531
• CAS DataBase Reference: 2-phenyl-1,3,2-dioxaphospholane 2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-1,3,2-dioxaphospholane 2-oxide(13468-89-8)
• EPA Substance Registry System: 2-phenyl-1,3,2-dioxaphospholane 2-oxide(13468-89-8)

Safety Data

• Hazardous Substances Data: 13468-89-8(Hazardous Substances Data)

Upstream product

• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 107-21-1 ethylene glycol 
• 34736-73-7 5-phenyl-1,4,6,9-tetraoxa-5-phosphaspiro<4.4>nonane 
• 644-97-3 Dichlorophenylphosphine 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 58816-54-9 1-(methoxy-phenyl-phosphinoyl)-5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester 
• 1571-33-1 phenylphosphonate 
• 4129-17-3 diphenylphosphoranyl azide 
• 1006-83-3 2-phenyl-[1,3,2]dioxaphospholane 
• 78133-06-9 C₁₄H₁₆NO₃P 
• 58816-57-2 O-Methyl-O-β-hydroxyaethyl-phenylphosphonat 
• 59259-22-2 bis(2-hydroxyethyl) phenylphosphonate 
• 75-21-8 oxirane 
• 55861-16-0 phenyl dioxophosphorane 

Downstream Products

• 10311-08-7 dimethyl(phenyl)phosphine oxide 

Relevant articles and documents

Direct conversion of phosphonates to phosphine oxides: An improved synthetic route to phosphines including the first synthesis of methyl JohnPhos

The synthesis of tertiary phosphine oxides from phosphonates was achieved reliably and in good to excellent yields using stoichiometric amounts of alkyl or aryl Grignard reagents and sodium trifluoromethanesulfonate (NaOTf). In the absence of the NaOTf additive, covalent coordination oligomers of magnesium and phosphorus species dominate the reaction, producing very low yields of phosphine oxide, but high conversions of the phosphonate starting material. Mechanistic studies revealed that a five-coordinate phosphorus species - not a phosphinate - is the reaction intermediate. A diverse array of phosphonates was converted to phosphine oxides using a variety of Grignard reagents for direct carbon-phosphorus functionalization. This new methodology especially simplifies the synthesis of dimethylphosphino (RPMe2)-type phosphines by using air-, water-, and silica-stable intermediates. To highlight this reaction, a new Buchwald-type ligand ([1,1′-biphenyl]-2-yldimethylphosphine, or methyl JohnPhos) and a classic bidentate phosphine, bis(diphenylphosphino)propane (dppp), were synthesized in excellent yields.

Conversions of 2-phenyl-1,3,2-dioxaphospholane under the action of hydrogen chloride

The reaction of 2-phenyl-1,3,2-dioxaphospholane with HCl gives a mixture of phenylphosphinic acid, bis(2-chloroethyl) phenylphosphonate, and phenylphosphine; therewith, intermediate oligomeric phosphonites, hydrophosphoryl compounds, and phosphoranes were detected. Thermal treatment of the reaction mixture results in formation of ethylene phenylphosphonate and (2-chloroethyl)phenylphosphinate.

Simple method for cleavage of phosphonic acid diesters to monoesters

Phosphonic acid dialkyl or diaryl esters give, on treatment with alkali azide or alkali iodide in DMF at 100°C, quantitatively and specifically the corresponding monoesters. The reaction is applied in a series of acyclic nucleotide analogs for the preparation of PMEA monoesters and related compounds.