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1,8-Diazabicyclo(5.4.0)undec-7-ene
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<h2 id="synthesis">Synthesis</h2> <p>DBU can be synthesised in three steps from <a href="/facts/Caprolactam/tT28x3tx">caprolactam</a> and <a href="/facts/Acrylonitrile/zvhfg050">acrylonitrile</a>. First, the nitrile undergoes an <a href="/facts/Addition_reaction/LvIngK0g">addition reaction</a> at the caprolactam nitrogen, producing <i>N</i>-(2-cyanoethyl)-caprolactam. This is then <a href="/facts/Hydrogenated/l7EzNSA7">hydrogenated</a> to <i>N</i>-aminopropyl-caprolactam, followed by an <a href="/facts/Intramolecular_reaction/a369zhCw">intramolecular</a> <a href="/facts/Carbonyl_condensation/d4XahHwm">carbonyl condensation</a> to form the imine. <a href="/facts/Water/0lkXnJPK">Water</a> is removed by fractional distillation.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> </p> <h2 id="occurrence">Occurrence</h2> <p>Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge <i><a href="/facts/Niphates_digitalis/wWRBGg8V">Niphates digitalis</a></i>.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> The biosynthesis of DBU has been proposed to begin with <a href="/facts/Adipaldehyde/xLJ6TTM8">adipaldehyde</a> and <a href="/facts/1%2c3-diaminopropane/xIYmu5kk">1,3-diaminopropane</a>. </p> <h2 id="applications">Applications</h2> <p>DBU is used: </p> <ul><li>As a <a href="/facts/Reagent/c3GLInCu">reagent</a> in organic chemistry, where DBU is used as a ligand and base. As a base, protonation occurs at the imine nitrogen.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> Lewis acids also attach to the same nitrogen.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a></li> <li>As a catalyst, for example as a <a href="/facts/Curing_agent/qHuInaQg">curing agent</a> for <a href="/facts/Epoxy/PvlLBgdQ">epoxy</a> resins and <a href="/facts/Polyurethane/qNo2KSXA">polyurethane</a>.</li> <li>In the separation of <a href="/facts/Fullerene/LPdnl8ox">fullerenes</a> in conjunction with <a href="/facts/1%2c2%2c4-Trimethylbenzene/KMjjRMkx">trimethylbenzene</a>. It reacts with <a href="/facts/C70_fullerene/hFe5HmpB">C70</a> and higher fullerenes, but not with <a href="/facts/Buckminsterfullerene/F0VebtPK">C60</a>.</li> <li>As a <a href="/facts/Dehydrohalogenation/Cx6JUTv0">dehydrohalogenation</a> agent.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a></li> <li>In surface activation products (<a href="/facts/Adhesive/shTfIJ0E">primers</a>) for low-<a href="/facts/Surface_energy/FYQruNIK">surface energy</a> plastics and elastomers (such as <a href="/facts/Polytetrafluoroethylene/jesBNXKq">PTFE</a>, <a href="/facts/High-density_polyethylene/9mUm98TQ">HDPE</a>, <a href="/facts/Polypropylene/HM9PvoCz">PP</a>, and <a href="/facts/Silicone_rubber/3XMpD7m9">silicone rubber</a>), where DBU raises the surface energy enough for adhesives (such as <a href="/facts/Cyanoacrylate/jLS7fkwR">cyanoacrylate</a> and <a href="/facts/Impact_glue/SetbHkhM">contact cement</a>) to bond to these otherwise inert, non-stick materials.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a></li></ul> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/1%2c5-Diazabicyclo(4.3.0)non-5-ene/JDQMrbu0">1,5-Diazabicyclo[4.3.0]non-5-ene</a></li> <li><a href="/facts/DABCO/wxkhFvru">DABCO</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Ghosh, Nandita (2004). "DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) - A Nucleophillic Base". Synlett (3): 574–575. doi:10.1055/s-2004-815436. <a href="https://doi.org/10.1055%2Fs-2004-815436" target="_blank">https://doi.org/10.1055%2Fs-2004-815436</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>CN patent 101279973, Bi Zuowen, Gao Hongbin, Cao Hongbo, Wang Xiaomei, Liu Change, Xu Qin, Zhang Zonghua, "Preparation of 1,8-diazabicyclo[5.4.0]undec-7-ene", issued 2010-06-02, assigned to Shandong Xinhua Wanbo Chemical <a href="https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=CN101279973" target="_blank">https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=CN101279973</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>E. L. Regalado; Judith Mendiola; Abilio Laguna; Clara Nogueiras; Olivier P Thomas (2010). "Polar alkaloids from the Caribbean marine sponge Niphates digitalis". Nat. Prod. Commun. 5 (8): 1187–1190. PMID 20839615. <a href="/wiki/PMID_(identifier)" target="_blank">/wiki/PMID_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Parviainen, Arno; King, Alistair W. T.; Mutikainen, Ilpo; Hummel, Michael; Selg, Christoph; Hauru, Lauri K. J.; Sixta, Herbert; Kilpeläinen, Ilkka (2013). "Predicting Cellulose Solvating Capabilities of Acid–Base Conjugate Ionic Liquids". ChemSusChem. 6 (11): 2161–2169. Bibcode:2013ChSCh...6.2161P. doi:10.1002/cssc.201300143. ISSN 1864-5631. PMID 24106149. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Romero, Erik A.; Zhao, Tianxiang; Nakano, Ryo; Hu, Xingbang; Wu, Youting; Jazzar, Rodolphe; Bertrand, Guy (2018-10-01). "Tandem copper hydride–Lewis pair catalysed reduction of carbon dioxide into formate with dihydrogen". Nature Catalysis. 1 (10): 743–747. doi:10.1038/s41929-018-0140-3. ISSN 2520-1158. <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>Savoca, Ann C.; Urgaonkar, Sameer (2006). "1,8-Diazabicyclo[5.4.0]undec-7-ene". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd011.pub2. ISBN 0-471-93623-5. <a href="0-471-93623-5" target="_blank">0-471-93623-5</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>"Novatio Silfix Primer SDS" (PDF). novatio.com. 2022. Archived from the original (PDF) on 2025-05-16. Retrieved 2025-05-16. <a href="https://web.archive.org/web/20250516111927/https://novatio.com/storage/files/87eab6b0-ac1a-4e81-87d8-af8743c9fd11/silfix-primer-sds-en-220714.pdf" target="_blank">https://web.archive.org/web/20250516111927/https://novatio.com/storage/files/87eab6b0-ac1a-4e81-87d8-af8743c9fd11/silfix-primer-sds-en-220714.pdf</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> </ol>