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Methyl fluorosulfonate
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<h2 id="synthesis-and-reactions">Synthesis and reactions</h2> <p>It is prepared by distillation of an equimolar mixture of <a href="/facts/Fluorosulfonic_acid/HJng4DqN">fluorosulfonic acid</a> and <a href="/facts/Dimethyl_sulfate/qHswLdl6">dimethyl sulfate</a>. It was originally produced by the reaction of <a href="/facts/Methanol/EIfpoNCg">methanol</a> with <a href="/facts/Fluorosulfuric_acid/HJng4DqN">fluorosulfonic acid</a>.<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a> </p><p>Methyl fluorosulfonate is a highly electrophilic reagent for <a href="/facts/Methylation/EvDMWVW5">methylation</a>. It is ranked as less powerful than methyl trifluoromethanesulfonate.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> </p> <h2 id="toxicity">Toxicity</h2> <p>Similar to <a href="/facts/Phosgene/Adeazsck">phosgene</a>, it is acutely toxic<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> by inhalation, with an <a href="/facts/LC50/PSTer8Wv">LC50</a> (rat, 1 hour) of about 5 ppm. Several cases of poisoning resulting in death from <a href="/facts/Pulmonary_edema/sVS5UDxl">pulmonary edema</a> have been reported.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Meyer, Julius; Schramm, Georg (1932). "Ester der Fluorsulfonsäure (Esters of fluorosulfonic acid)". Zeitschrift für Anorganische und Allgemeine Chemie. 206: 24–30. doi:10.1002/zaac.19322060103. <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>Stang, Peter J.; Hanack, Michael; Subramanian, L. R. (1982). "Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry". Synthesis. 1982 (2): 85–126. doi:10.1055/s-1982-29711. ISSN 0039-7881. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Meyer, Julius; Schramm, Georg (1932). "Ester der Fluorsulfonsäure (Esters of fluorosulfonic acid)". Zeitschrift für Anorganische und Allgemeine Chemie. 206: 24–30. doi:10.1002/zaac.19322060103. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Hite, M.; Rinehart, W.; Braun, W.; Peck, H. (1979). "Acute toxicity of methyl fluorosulfonate (Magic Methyl)". AIHA Journal. 40 (7): 600–603. doi:10.1080/00028897708984416. PMID 484483. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> </ol>