Dimethylphosphine oxide

<h2 id="preparation">Preparation</h2>
<p>The compound arises by the hydrolysis of chlorodimethylphosphine:<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a>
</p>
Me2PCl  +  H2O  →   Me2P(O)H  +  HCl
<p>Methanol, but not ethanol, can also be used in place of water, the co-product being <a href="/facts/Methyl_chloride/DvmeEgDS">methyl chloride</a>.
</p><p>Since chlorodimethylphosphine is dangerous to handle, alternative routes to dimethylphosphine oxide have been developed.  A popular method starts with <a href="/facts/Diethylphosphite/9mMJegDl">diethylphosphite</a>, according to the following idealized equations:<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a>
</p>
(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)
<h2 id="reactions">Reactions</h2>
<p>Chlorination gives dimethylphosphoryl chloride.  It undergoes hydroxymethylation with formaldehyde.  
</p>
Me2P(O)H  +  CH2O   →   Me2P(O)CH2OH
<p>Many aldehydes effect a similar reaction. 
</p>

<h2 id="references">References</h2>

<ol>
<li id="fn:1"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li>
<li id="fn:2"><p>Hays, H. R. (1968). "Reaction of diethyl phosphonate with methyl and ethyl Grignard reagents". J. Org. Chem. 33: 3690–3694. doi:10.1021/jo01274a003. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li>
</ol>

Dimethylphosphine oxide open-in-new

Dimethylphosphine oxide