Dimethylphosphite

Dimethylphosphite

Names
Preferred IUPAC name Dimethyl phosphonate
Other names Phosphonic acid, dimethyl ester
Identifiers
CAS Number	868-85-9  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL65359
ChemSpider	85582
ECHA InfoCard	100.011.622
PubChem CID	94853
UNII	ST4TBO000H  Y
CompTox Dashboard (EPA)	DTXSID5020493
InChI InChI=1S/C2H7O3P/c1-4-6(3)5-2/h3H,1-2H3 Key: DLQDGVZAEYZNTG-UHFFFAOYSA-N
SMILES COP(O)OC
Properties
Chemical formula	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). Infobox references

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]

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 .