Methylphosphonic acid

Methylphosphonic acid
Identifiers
993-13-5
ChEBI CHEBI:45129
ChemSpider 13220
EC Number 213-607-2
Jmol interactive 3D Image
KEGG C20396
MeSH C032627
PubChem 13818
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

The dialkylphosphonate is then treated with chlorotrimethylsilane:

CH3PO(OC2H5)2 + 2 Me3SiCl → CH3PO(OSiMe3)2 + 2 ClC2H5

The siloxyphosphinate is then hydrolyzed:

CH3PO(OSiMe3)2 + 2H2O → CH3PO(OH)2 + 2 HOSiMe3

References

  1. "Methylphosphonic Acid". Sigma-Aldrich. Retrieved 12 December 2013.
  2. "methylphosphonic acid - Compound Summary". NCBI. Retrieved 12 December 2013.
  3. 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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