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Dimethylphosphite

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Dimethylphosphite
Names
Preferred IUPAC name Dimethyl phosphonate
Other names Phosphonic acid, dimethyl ester
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.011.622 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H7O3P/c1-4-6(3)5-2/h3H,1-2H3Key: DLQDGVZAEYZNTG-UHFFFAOYSA-N
SMILES
  • COP(O)OC
Properties
Chemical formula C2H7O3P
Molar mass 110.049 g·mol
Appearance colorless liquid
Density 1.20 g/cm
Boiling point 72–73 °C (162–163 °F; 345–346 K) 25 Torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Dimethylphosphite is an organophosphorus compound with the formula (CH3O)2P(O)H, known as dimethyl hydrogen phosphite (DMHP). Dimethylphosphite, is a minor tautomer of the phosphorus(V) derivative. It is a reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. The molecule is tetrahedral. It is a colorless liquid. The compounds can be prepared by methanolysis of phosphorus trichloride or by heating diethylphosphite in methanol.

Although studies have not been reported for this compound, the closely related diethylphosphite exists predominantly as the phosphorus(V) tautomer.

References

  1. Balint, Erika; Tajti, Adam; Drahos, Laszlo; Ilia, Gheorge; Keglevich, Gyorgy (2013). "Alcoholysis of Dialkyl Phosphites Under Microwave Conditions". Current Organic Chemistry. 17 (5): 555–562. doi:10.2174/1385272811317050010.
  2. Guthrie, J. Peter (1979). "Tautomerization Equilibria for Phosphorous Acid and its Ethyl Esters, Free Energies of Formation of Phosphorous and Phosphonic Acids and their Ethyl Esters, and p Ka Values for Ionization of the P—H Bond in Phosphonic Acid and Phosphonic Esters". Canadian Journal of Chemistry. 57 (2): 236–239. doi:10.1139/v79-039.
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