Dimethylphosphine oxide

Dimethylphosphine oxide
Names
	Other names dimethylphosphinous acid tautomer
Identifiers
CAS Number	7211-39-4;
3D model (JSmol)	Interactive image;
ChemSpider	10415346;
EC Number	230-591-2;
PubChem CID	81631;
	InChI InChI=1S/C2H7OP/c1-4(2)3/h4H,1-2H3 Key: HGDIHUZVQPKSMO-UHFFFAOYSA-N;
	SMILES CP(=O)C;
Properties
Chemical formula	C2H7OP
Molar mass	78.051 g·mol−1
Appearance	colorless liquid
Boiling point	65-67 ºC
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H315, H319, H335
GHS precautionary statements	P261, P264, P270, P271, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313, P362, P403+233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Dimethylphosphine oxide is an organophosphorus compound with the formula (CH₃)₂P(O)H. It is a colorless liquid that soluble in polar organic solvents. It exists as the phosphine oxide, not the hydroxy tautomer. A related compound is diphenylphosphine oxide. Both are sometimes called secondary phosphine oxides.

Preparation

The compound arises by the hydrolysis of chlorodimethylphosphine:[1]

Me₂PCl + H₂O → Me₂P(O)H + HCl

Methanol, but not ethanol, can also be used in place of water, the co-product being methyl chloride.

Since chlorodimethylphosphine is dangerous to handle, alternative routes to dimethylphosphine oxide have been developed. A popular method starts with diethylphosphite, according to the following idealized equations:[2]

(C₂H₅O)₂P(O)H + 3 CH₃MgBr → (CH₃)₂P(O)MgBr + 2 MgBr(OC₂H₅) + CH₄

(CH₃)₂P(O)MgBr + H₂O → (CH₃)₂P(O)H + 2 MgBr(OH)

Reactions

Chlorination gives dimethylphosphoryl chloride. It undergoes hydroxymethylation with formaldehyde.

Me₂P(O)H + CH₂O → Me₂P(O)CH₂OH

Many aldehydes effect a similar reaction.

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References

Kleiner, H. J. (1974). "Herstellung und Umsetzungen von Dimethylphosphinoxid (Preparation and Reactions of Dimethylphosphine Oxide)". Justus Liebigs Ann. Chem.: 751–764. doi:10.1002/jlac.197419740507.
Hays, H. R. (1968). "Reaction of diethyl phosphonate with methyl and ethyl Grignard reagents". J. Org. Chem. 33: 3690–3694. doi:10.1021/jo01274a003.

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[1] Kleiner, H. J. (1974). "Herstellung und Umsetzungen von Dimethylphosphinoxid (Preparation and Reactions of Dimethylphosphine Oxide)". Justus Liebigs Ann. Chem.: 751–764. doi:10.1002/jlac.197419740507.

[2] Hays, H. R. (1968). "Reaction of diethyl phosphonate with methyl and ethyl Grignard reagents". J. Org. Chem. 33: 3690–3694. doi:10.1021/jo01274a003.