Dimethylphosphite

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.

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	170–171 °C (338–340 °F; 443–444 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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.^[1]

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

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.