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Mesylate
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<h2 id="preparation">Preparation</h2> <p>Mesylate esters are generally prepared by treating an alcohol and <a href="/facts/Methanesulfonyl_chloride/8qMTp4rg">methanesulfonyl chloride</a> in the presence of a <a href="/facts/Base_(chemistry)/M9wA7qeM">base</a>, such as <a href="/facts/Triethylamine/6DjzaGGv">triethylamine</a>.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> </p> <h2 id="mesyl">Mesyl</h2> <p>Related to mesylate is the mesyl (Ms) or methanesulfonyl (CH3SO2) functional group. The shortened term itself was coined by <a href="/facts/Burckhardt_Helferich/pRXbsggT">Helferich</a> et al. in 1938 similarly to <a href="/facts/Tosyl_group/Q4qU62D1">tosyl</a> adopted earlier.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> <a href="/facts/Methanesulfonyl_chloride/8qMTp4rg">Methanesulfonyl chloride</a> is often referred to as mesyl chloride. </p><p>Whereas mesylates are often <a href="/facts/Hydrolysis/JTvwIHPs">hydrolytically</a> labile, mesyl groups, when attached to <a href="/facts/Nitrogen/Nf1QpGDz">nitrogen</a>, are resistant to hydrolysis.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> This <a href="/facts/Functional_group/GXkSPsjM">functional group</a> appears in a variety of medications, particularly <a href="/facts/Cardiac/fF4KSGdk">cardiac</a> (<a href="/facts/Antiarrhythmic/RJPHtxKr">antiarrhythmic</a>) drugs, as a <a href="/facts/Sulfonamide/h1sVXW41">sulfonamide</a> moiety. Examples include <a href="/facts/Sotalol/MKeKwlKq">sotalol</a>, <a href="/facts/Ibutilide/hscFMadc">ibutilide</a>, <a href="/facts/Sematilide/DBXztwnt">sematilide</a>, <a href="/facts/Dronedarone/lrHIzj2T">dronedarone</a>, <a href="/facts/Dofetilide/7NBVAVhA">dofetilide</a>, <a href="/facts/E-4031/QCTa8vtA">E-4031</a>, and <a href="/facts/Bitopertin/JVaNvgGy">bitopertin</a>. </p> <h2 id="natural-occurrence">Natural occurrence</h2> <p>Ice core samples from a single spot in Antarctica were found to have tiny inclusions of magnesium methanesulfonate dodecahydrate. This natural phase is recognized as the mineral ernstburkeite. It is extremely rare.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a><a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Tosylate/Q4qU62D1">Tosylate</a></li> <li><a href="/facts/Triflate/6sbvDSyt">Triflate</a>, the fluorinated analog of mesylate.</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>International Nonproprietary Names Modified (PDF) (Report). World Health Organization. February 2006. INN Working Document 05.167/3. Retrieved 5 December 2008. <a href="https://www.who.int/medicines/services/inn/INNMreview%20paperWkDoc167_Feb06_3_.pdf" target="_blank">https://www.who.int/medicines/services/inn/INNMreview%20paperWkDoc167_Feb06_3_.pdf</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. p. 497. ISBN 978-0-471-72091-1. <a href="978-0-471-72091-1" target="_blank">978-0-471-72091-1</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Rick L. Danheiser; Yeun-Min Tsai; David M. Fink (1966). "A General Method for the Synthesis of Allenylsilanes: 1-Methyl-1-(trimethylsilyl)allene". Organic Syntheses. doi:10.15227/orgsyn.066.0001. (a procedure illustrating the use of mesylates). <a href="/wiki/Rick_L._Danheiser" target="_blank">/wiki/Rick_L._Danheiser</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Helferich, Burckhardt; Gnüchtel, Alfred (6 April 1938). "Ester der Methansulfonsäure in der Zuckergruppe". Berichte der deutschen chemischen Gesellschaft (A and B Series) (in German). 71 (4): 712–718. doi:10.1002/cber.19380710403. ISSN 0365-9488. <a href="https://onlinelibrary.wiley.com/doi/10.1002/cber.19380710403" target="_blank">https://onlinelibrary.wiley.com/doi/10.1002/cber.19380710403</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Valerie Vaillancourt, Michele M. Cudahy, Matthew M. Kreilein and Danielle L. Jacobs "Methanesulfonyl Chloride" in E-EROS Encyclopedia for Reagents in Organic Synthesis. doi:10.1002/047084289X.rm070.pub2 <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Güner, Fatma Elif Genceli; Sakurai, Toshimitsu; Hondoh, Takeo (2013). "Ernstburkeite, Mg(CH3SO3)2·12H2O, a new mineral from Antarctica". European Journal of Mineralogy. 25 (1): 78–83. Bibcode:2013EJMin..25...78G. doi:10.1127/0935-1221/2013/0025-2257. <a href="https://www.schweizerbart.de/papers/ejm/detail/25/79543/Ernstburkeite_MgCH3SO3212H2O_a_new_mineral_from_Antarctica" target="_blank">https://www.schweizerbart.de/papers/ejm/detail/25/79543/Ernstburkeite_MgCH3SO3212H2O_a_new_mineral_from_Antarctica</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Ernstburkeite, Mindat <a href="http://www.mindat.org/min-41897.html" target="_blank">http://www.mindat.org/min-41897.html</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> </ol>