Methylphosphonic acid
Identifiers | |
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993-13-5 | |
3D model (Jmol) | Interactive image |
ChEBI | CHEBI:45129 |
ChemSpider | 13220 |
ECHA InfoCard | 100.012.370 |
EC Number | 213-607-2 |
KEGG | C20396 |
MeSH | C032627 |
PubChem | 13818 |
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Properties | |
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 references | |
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]
Preparation
Methylphosphonic acid can be prepared via the Michaelis-Arbuzov reaction from triethylphosphite:[3]
- CH3Cl + P(OC2H5)3 → CH3PO(OC2H5)2 + C2H5Cl
The dialkylphosphonate is then treated with chlorotrimethylsilane:
- CH3PO(OC2H5)2 + 2 Me3SiCl → CH3PO(OSiMe3)2 + 2 C2H5Cl
The siloxyphosphinate is then hydrolyzed:
- CH3PO(OSiMe3)2 + 2H2O → CH3PO(OH)2 + 2 HOSiMe3
References
- ↑ "Methylphosphonic Acid". Sigma-Aldrich. Retrieved 12 December 2013.
- ↑ "methylphosphonic acid - Compound Summary". NCBI. Retrieved 12 December 2013.
- ↑ Katritzky, Pilarski, Alan, Boguslaw. "A One-Pot Procedure For the Preparation of Phosphonic Acids From Alkyl Halides" (PDF). Retrieved 12 December 2013.
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