Methylphosphonic acid
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]
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| ChemSpider | |
| ECHA InfoCard | 100.012.370 |
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| MeSH | C032627 |
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CompTox Dashboard (EPA) |
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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). | |
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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
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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). Archived from the original (PDF) on 23 September 2015. Retrieved 12 December 2013.
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