15286-18-7

Basic information

• Product Name: dimethyl (3-methoxyphenyl)phosphonate
• Synonyms: dimethyl (3-methoxyphenyl)phosphonate
• CAS NO: 15286-18-7
• Molecular Weight: 216.174
• Mol File: 15286-18-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: dimethyl (3-methoxyphenyl)phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl (3-methoxyphenyl)phosphonate(15286-18-7)
• EPA Substance Registry System: dimethyl (3-methoxyphenyl)phosphonate(15286-18-7)

Safety Data

• Hazardous Substances Data: 15286-18-7(Hazardous Substances Data)

Upstream product

• 766-85-8 3-methoxy-1-iodobenzene 
• 868-85-9 Dimethyl phosphite 
• 2398-37-0 3-methoxyphenyl bromide 
• 121-45-9 phosphorous acid trimethyl ester 

Relevant articles and documents

Photoinduced Transition-Metal-Free Cross-Coupling of Aryl Halides with H-Phosphonates

Photoinduced transition-metal- and photosensitizer-free cross-coupling of aryl halides (including Ar-Cl, Ar-Br, and Ar-I) with H-phosphonates (including dialkyl phosphonates and diarylphosphine oxides) is reported. Various functional groups were tolerated, including ester, methoxy, dimethoxy, alkyl, phenyl, trifluoromethyl, and heterocyclic compounds. This simple and green strategy provides a practical pathway to synthesize arylphosphine oxides.

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.