Methylphosphonic acid is an organophosphorus compound with the chemical formula CH3P(O)(OH)2. The phosphorus center is tetrahedral and is bonded to a methyl group, two OH groups and an oxygen. Methylphosphonic acid is a white, non-volatile solid that is poorly soluble in organic solvent but soluble in water and common alcohols.[2]
The resulting dialkylphosphonate is then treated with chlorotrimethylsilane before hydrolysis of the siloxyphosphonate to generate the desired product.[3]
The reaction pathway proceeds via the siloxyphosphonate intermediate due to the difficulty in directly hydrolysing dialkylphosphonates. Katritzky and co-workers published a one-pot synthesis of methylphosphonic acid in 1989.[3]
Referencesedit
^"Methylphosphonic Acid". Sigma-Aldrich. Retrieved 12 December 2013.
^"methylphosphonic acid - Compound Summary". NCBI. Retrieved 12 December 2013.
^ abcKatritzky, Alan R.; Pilarski, Boguslaw; Johnson, Jack W. (1989). "A One-Pot Procedure For the Preparation of Phosphonic Acids From Alkyl Halides". The New Journal for Organic Synthesis. 22 (2): 209–213. doi:10.1080/00304949009458197.
January 01, 1970
methylphosphonic, acid, organophosphorus, compound, with, chemical, formula, ch3p, phosphorus, center, tetrahedral, bonded, methyl, group, groups, oxygen, white, volatile, solid, that, poorly, soluble, organic, solvent, soluble, water, common, alcohols, identi. Methylphosphonic acid is an organophosphorus compound with the chemical formula CH3P O OH 2 The phosphorus center is tetrahedral and is bonded to a methyl group two OH groups and an oxygen Methylphosphonic acid is a white non volatile solid that is poorly soluble in organic solvent but soluble in water and common alcohols 2 Methylphosphonic acid Identifiers CAS Number 993 13 5 Y 3D model JSmol Interactive image ChEBI CHEBI 45129 ChemSpider 13220 ECHA InfoCard 100 012 370 EC Number 213 607 2 KEGG C20396 MeSH C032627 PubChem CID 13818 UNII 329W4YM10Z Y CompTox Dashboard EPA DTXSID5047748 InChI InChI 1S CH5O3P c1 5 2 3 4 h1H3 H2 2 3 4 Key YACKEPLHDIMKIO UHFFFAOYSA NInChI 1 CH5O3P c1 5 2 3 4 h1H3 H2 2 3 4 Key YACKEPLHDIMKIO UHFFFAOYAB SMILES CP O O O Properties Chemical formula CH5O3P Molar mass 96 02 Appearance White Solid Melting point 105 to 107 C 221 to 225 F 378 to 380 K 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesPreparation editMethylphosphonic acid can be prepared from triethylphosphite by first using a Michaelis Arbuzov reaction to generate the phosphorus V centre 3 CH3Cl P OC2H5 3 CH3PO OC2H5 2 C2H5Cl The resulting dialkylphosphonate is then treated with chlorotrimethylsilane before hydrolysis of the siloxyphosphonate to generate the desired product 3 CH3PO OC2H5 2 2 Me3SiCl CH3PO OSiMe3 2 2 C2H5Cl CH3PO OSiMe3 2 2H2O CH3PO OH 2 2 HOSiMe3 The reaction pathway proceeds via the siloxyphosphonate intermediate due to the difficulty in directly hydrolysing dialkylphosphonates Katritzky and co workers published a one pot synthesis of methylphosphonic acid in 1989 3 References edit Methylphosphonic Acid Sigma Aldrich Retrieved 12 December 2013 methylphosphonic acid Compound Summary NCBI Retrieved 12 December 2013 a b c Katritzky Alan R Pilarski Boguslaw Johnson Jack W 1989 A One Pot Procedure For the Preparation of Phosphonic Acids From Alkyl Halides The New Journal for Organic Synthesis 22 2 209 213 doi 10 1080 00304949009458197 Retrieved from https en wikipedia org w index php title Methylphosphonic acid amp oldid 1197017491, wikipedia, wiki, book, books, library,
