Trimethyl phosphate

<h2 id="production">Production</h2>
<p>Trimethyl phosphate is prepared by treating <a href="/facts/Phosphorus_oxychloride/fwbrqPWI">phosphorus oxychloride</a> with <a href="/facts/Methanol/EIfpoNCg">methanol</a> in the presence of an <a href="/facts/Amine/JvfYJfP6">amine</a> base:
</p>
POCl3  +  3  CH3OH  +  3 R3N   →     PO(OCH3)3  +  3 R3NH+Cl−
<p>It is a <a href="/facts/Tetrahedral_molecule/583AL1sP">tetrahedral molecule</a> that is a weakly polar solvent.
</p>
<h2 id="applications">Applications</h2>
<p>Trimethyl phosphate is a mild <a href="/facts/Methylation/EvDMWVW5">methylating agent</a>, useful for dimethylation of <a href="/facts/Aniline/eFXck1Rj">anilines</a> and related <a href="/facts/Heterocyclic_compounds/8oYSjJxY">heterocyclic compounds</a>.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a>  The method is complementary to the traditional <a href="/facts/Eschweiler-Clarke_reaction/nECJjadu">Eschweiler-Clarke reaction</a> in cases where formaldehyde engages in side reactions.
</p><p>Trimethyl phosphate is used as a <a href="/facts/Solvent/LoMPMz8S">solvent</a> for <a href="/facts/Aromatic/wK0DzRY6">aromatic</a> <a href="/facts/Halogenations/vYrGVWcJ">halogenations</a> and <a href="/facts/Nitrations/VnszL09H">nitrations</a> as required for the preparation of <a href="/facts/Pesticides/Uhf4KnwJ">pesticides</a> and <a href="/facts/Pharmaceuticals/h9mhwWP2">pharmaceuticals</a>.
</p>
<h3>Other applications</h3>
<p>It is used as a color inhibitor for fibers (e.g. <a href="/facts/Polyester/Ivp9CHpl">polyester</a>) and other <a href="/facts/Polymers/eF32E50K">polymers</a>. Trimethyl phosphate is used as a <a href="/facts/Simulation/Q4QJV1oI">simulant</a> for <a href="/facts/Chemical_weapon/AwXDDhAR">chemical weapon</a> <a href="/facts/Nerve_agents/5UcsLz9R">nerve agents</a>.
</p>
<h2 id="safety-considerations">Safety considerations</h2>
<p>With an <a href="/facts/LD50/PSTer8Wv">LD50</a> of 2g/kg for rats, trimethylphosphate is expected to have low acute toxicity.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a>
</p>

<h2 id="external-links">External links</h2>
<ul><li><a href="http://webbook.nist.gov/cgi/cbook.cgi?ID=C512561">WebBook page for C3H9PO4</a></li></ul>

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

<ol>
<li id="fn:1"><p>D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam 1995. ISBN 0-444-89307-5. <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li>
<li id="fn:2"><p>William A. Sheppard (1973). "m-Trifluoromethyl-N,N-dimethylaniline". Organic Syntheses; Collected Volumes, vol. 5, p. 1085.
 <a href="http://www.orgsyn.org/demo.aspx?prep=CV5P1085" target="_blank">http://www.orgsyn.org/demo.aspx?prep=CV5P1085</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li>
<li id="fn:3"><p>J. Svara,  N. Weferling, T. Hofmann "Phosphorus Compounds, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. doi:10.1002/14356007.a19_545.pub2 <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li>
</ol>

Trimethyl phosphate open-in-new

Trimethyl phosphate