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Dimethylphosphite

From Wikipedia, the free encyclopedia
Dimethylphosphite
Names
Preferred IUPAC name
Dimethyl phosphonate
Other names
Phosphonic acid, dimethyl ester
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.011.622 Edit this at Wikidata
UNII
  • InChI=1S/C2H7O3P/c1-4-6(3)5-2/h3H,1-2H3
    Key: DLQDGVZAEYZNTG-UHFFFAOYSA-N
  • COP(O)OC
Properties
C2H7O3P
Molar mass 110.049 g·mol−1
Appearance colorless liquid
Density 1.20 g/cm3
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 [77 °F], 100 kPa).

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.[1]

Although studies have not been reported for this compound, the closely related diethylphosphite exists predominantly as the phosphorus(V) tautomer.[2]

This tautomeric nature of DMHP made it desirable as a precursor to the G-series compounds, and it was the most successful among all other phosphonate precursors.[3] The now obsolete process, which used it as a precursor, was called the DMHP process, investigated by Otto Ambros' team and implemented to scale sarin production.[4]

References

[edit]
  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.
  3. ^ Sipri - Chemical Weapons: Destruction and Conversion. p 57-62
  4. ^ Mark A. Prelas, Dabir S. Viswanath,. Science and Technology of Terrorism and Counterterrorism, Second lllllEdition. p 341-342.