1,8-Diazabicyclo(5.4.0)undec-7-ene

Chemical compound bracket 1,8-Diazabicyclo[5.4.0]undec-7-ene changed 477206737 1,8-Diazabicyclo[5.4.0]undec-7-ene DBU.svg DBU-3D-balls.png DBU molecule 2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine DBU, Diazabicycloundecene N\2=C1\N(CCCCC1)CCC/2 correct chemspider 73246 1/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 GQHTUMJGOHRCHB-UHFFFAOYAM correct chemspider 1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 correct chemspider GQHTUMJGOHRCHB-UHFFFAOYSA-N correct CAS 6674-22-2 81184 229-713-7 H1ILJ6IBUX 9 16 2 Colorless liquid 1.018 g/mL liquidMay 2025 ethers, alcohols -70 261 (1 atm),80 to 83 °C (0.6 mmHg) 13.5±1.5 Kaupmees, K. Trummal, A. Leito, I. Basicities of Strong Bases in Water: A Computational Study Croat. Chem. Acta 2014 87 4 385–395 10.5562/cca2472 free (pKa of conjugate acid in water); 24.34 Kaljurand, I. Kütt, A. Sooväli, L. Rodima, T. Mäemets, V. Leito, I. Koppel, I. A. Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales J. Org. Chem. 2005 70 3 1019–1028 10.1021/jo048252w 15675863 (pKa of conjugate acid in acetonitrile) 119.9 05 06 07 Danger 301 302 312 314 412 260 264 270 273 280 301+310 301+312 301+330+331 302+352 303+361+353 304+340 305+351+338 310 312 321 322 330 363 405 501 1,8-Diazabicyclo[5.4.0]undec-7-ene, or more commonly DBU, is a chemical compound and belongs to the class of amidine compounds. It is used in organic synthesis as a catalyst, a complexing ligand, and a non-nucleophilic base.10.1055/s-2004-815436 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) - A Nucleophillic Base Synlett 3 574–575 2004 Ghosh Nandita free Synthesis DBU can be synthesised in three steps from caprolactam and acrylonitrile. First, the nitrile undergoes an addition reaction at the caprolactam nitrogen, producing N-(2-cyanoethyl)-caprolactam. This is then hydrogenated to N-aminopropyl-caprolactam, followed by an intramolecular carbonyl condensation to form the imine. Water is removed by fractional distillation.CN 101279973 patent Preparation of 1,8-diazabicyclo[5.4.0]undec-7-ene Bi Zuowen, Gao Hongbin, Cao Hongbo, Wang Xiaomei, Liu Change, Xu Qin, Zhang Zonghua Shandong Xinhua Wanbo Chemical 2010-06-02 Occurrence Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge Niphates digitalis.E. L. Regalado Judith Mendiola Abilio Laguna Clara Nogueiras Olivier P Thomas Nat. Prod. Commun. 2010 5 Polar alkaloids from the Caribbean marine sponge Niphates digitalis 8 1187–1190 20839615 The biosynthesis of DBU has been proposed to begin with adipaldehyde and 1,3-diaminopropane. 500px|center|thumb|Proposed pathway for the biosynthesis of DBU in sponges. Applications DBU is used: As a reagent in organic chemistry, where DBU is used as a ligand and base. As a base, protonation occurs at the imine nitrogen.Parviainen Arno King Alistair W. T. Mutikainen Ilpo Hummel Michael Selg Christoph Hauru Lauri K. J. Sixta Herbert Kilpeläinen Ilkka Predicting Cellulose Solvating Capabilities of Acid–Base Conjugate Ionic Liquids ChemSusChem 6 11 2013 1864-5631 10.1002/cssc.201300143 2161–2169 24106149 2013ChSCh...6.2161P Lewis acids also attach to the same nitrogen.Romero Erik A. Zhao Tianxiang Nakano Ryo Hu Xingbang Wu Youting Jazzar Rodolphe Bertrand Guy Tandem copper hydride–Lewis pair catalysed reduction of carbon dioxide into formate with dihydrogen Nature Catalysis 1 10 2018-10-01 2520-1158 10.1038/s41929-018-0140-3 743–747 As a catalyst, for example as a curing agent for epoxy resins and polyurethane.May 2025 In the separation of fullerenes in conjunction with trimethylbenzene. It reacts with C70 and higher fullerenes, but not with C60.February 2026 As a dehydrohalogenation agent.10.1002/047084289X.rd011.pub2 1,8-Diazabicyclo[5.4.0]undec-7-ene Encyclopedia of Reagents for Organic Synthesis 2006 Savoca Ann C. Urgaonkar Sameer 0-471-93623-5 In surface activation products (primers) for low-surface energy plastics and elastomers (such as PTFE, HDPE, PP, and silicone rubber), where DBU raises the surface energy enough for adhesives (such as cyanoacrylate and contact cement) to bond to these otherwise inert, non-stick materials.2022 Novatio Silfix Primer SDS https://novatio.com/storage/files/87eab6b0-ac1a-4e81-87d8-af8743c9fd11/silfix-primer-sds-en-220714.pdf https://web.archive.org/web/20250516111927/https://novatio.com/storage/files/87eab6b0-ac1a-4e81-87d8-af8743c9fd11/silfix-primer-sds-en-220714.pdf 2025-05-16 2025-05-16 novatio.com See also 1,5-Diazabicyclo[4.3.0]non-5-ene DABCO References Category:Amidines Category:Reagents for organic chemistry Category:Non-nucleophilic bases