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Dimethyl acetylenedicarboxylate
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<h2 id="preparation">Preparation</h2> <p>Although inexpensively available, DMAD is prepared today as it was originally. <a href="/facts/Maleic_acid/cdMjU0Lb">Maleic acid</a> is <a href="/facts/Bromination/vYrGVWcJ">brominated</a> and the resulting dibromo<a href="/facts/Succinic_acid/v3KJqrQC">succinic acid</a> is <a href="/facts/Dehydrohalogenation/Cx6JUTv0">dehydrohalogenated</a> with <a href="/facts/Potassium_hydroxide/NBhPBuXc">potassium hydroxide</a> yielding <a href="/facts/Acetylenedicarboxylic_acid/aJ9vcJHE">acetylenedicarboxylic acid</a>.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a><a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> The acid is then <a href="/facts/Esterification/FoUAIIw4">esterified</a> with <a href="/facts/Methanol/EIfpoNCg">methanol</a> and <a href="/facts/Sulfuric_acid/Wom6fymJ">sulfuric acid</a> as a catalyst:<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <h2 id="safety">Safety</h2> <p>DMAD is a <a href="/facts/Lachrymator/SLJoBYEN">lachrymator</a> and a <a href="/facts/Vesicant/5w33WIKa">vesicant</a>.<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="references">References</h2> <ol> <li id="fn:1"><p>Stelmach, J. E.; Winkler, J. D. "Dimethyl Acetylenedicarboxylate"in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X. <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>Sahoo, Manoj (2007). "Dimethyl Acetylene Dicarboxylate". Synlett. 2007 (13): 2142–2143. doi:10.1055/s-2007-984894. <a href="https://doi.org/10.1055%2Fs-2007-984894" target="_blank">https://doi.org/10.1055%2Fs-2007-984894</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Bandrowski, E. (1877). "Ueber Acetylendicarbonsäure". Berichte der Deutschen Chemischen Gesellschaft. 10: 838–842. doi:10.1002/cber.187701001231. <a href="https://zenodo.org/record/1425134" target="_blank">https://zenodo.org/record/1425134</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Abbott, T. W.; Arnold, R. T.; Thompson, R. B. (1938). "Acetylenedicarboxylic acid". Organic Syntheses. 18: 3. doi:10.15227/orgsyn.018.0003; Collected Volumes, vol. 2, p. 10. <a href="http://www.orgsyn.org/demo.aspx?prep=cv2p0010" target="_blank">http://www.orgsyn.org/demo.aspx?prep=cv2p0010</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Huntress, E. H.; Lesslie, T. E.; Bornstein, J. (1952). "Dimethyl Acetylenedicarboxylate". Organic Syntheses. 32: 55. doi:10.15227/orgsyn.032.0055; Collected Volumes, vol. 4, p. 329. <a href="http://www.orgsyn.org/demo.aspx?prep=cv4p0329" target="_blank">http://www.orgsyn.org/demo.aspx?prep=cv4p0329</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Klain, G (May 1988). "Metabolic alterations induced by topical dimethylacetylenedicarboxylate*1". Fundamental and Applied Toxicology. 10 (4): 730–735. doi:10.1016/0272-0590(88)90199-6. <a href="https://linkinghub.elsevier.com/retrieve/pii/0272059088901996" target="_blank">https://linkinghub.elsevier.com/retrieve/pii/0272059088901996</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Slovak, A. J. M.; Payne, A. R. (June 1984). "Delayed dermal burns caused by dimethyl acetylenedicarboxylate". Contact Dermatitis. 11 (1): 29–30. doi:10.1111/j.1600-0536.1984.tb00166.x. ISSN 0105-1873. <a href="https://onlinelibrary.wiley.com/doi/10.1111/j.1600-0536.1984.tb00166.x" target="_blank">https://onlinelibrary.wiley.com/doi/10.1111/j.1600-0536.1984.tb00166.x</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> </ol>