| Revision as of 16:32, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475471172 of page 1,8-Diazabicycloundec-7-ene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 02:12, 23 October 2024 edit Citation bot (talk | contribs)Bots5,391,781 edits Add: bibcode, pmid, authors 1-1. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Dominic3203 | Category:Reagents for organic chemistry | #UCB_Category 94/228 |
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{{short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{correct title|reason=bracket|title=1,8-Diazabicycloundec-7-ene}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 444320828 |
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| verifiedrevid = 477206737 |
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| Name = 1,8-Diazabicycloundec-7-ene |
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| Name = 1,8-Diazabicycloundec-7-ene |
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| ImageFile = DBU.svg |
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| ImageFile = DBU.svg |
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| ImageName = |
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| ImageName = |
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| ImageFile1 = DBU-3D-balls.png |
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| IUPACName = 2,3,4,6,7,8,9,10-octahydropyrimidoazepine |
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| ImageAlt1 = DBU molecule |
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| OtherNames = DBU,Diazabicycloundecene |
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| PIN = 2,3,4,6,7,8,9,10-Octahydropyrimidoazepine |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = DBU, Diazabicycloundecene |
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| SMILES = N\2=C1\N(CCCCC1)CCC/2 |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SMILES = N\2=C1\N(CCCCC1)CCC/2 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 73246 |
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| ChemSpiderID = 73246 |
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| InChI = 1/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 |
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| InChI = 1/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 6674-22-2 |
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| CASNo = 6674-22-2 |
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| RTECS = |
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| PubChem = 81184 |
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| EC_number = 229-713-7 |
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| UNII = H1ILJ6IBUX |
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| RTECS = |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=9|H=16|N=2 |
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| Formula = C<sub>9</sub>H<sub>16</sub>N<sub>2</sub> |
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| Appearance = Colorless liquid |
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| MolarMass = 152.24 g/mol |
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| Appearance = Colorless liquid |
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| Density = 1.018 g/mL liquid |
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| Solubility = ethers, alcohols |
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| Density = 1.018 g/mL liquid |
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| MeltingPtC = -70 |
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| Solubility = |
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| MeltingPtC = -70 |
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| BoilingPtC = 261 |
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| BoilingPt = 80-83 °C (0.6 mmHg) |
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| BoilingPt_notes = (1 atm),<br/>80 to 83 °C (0.6 mmHg) |
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| pKa = 24.34 (in ])<ref name="Kaljurand">I. Kaljurand, A. Kütt, L. Sooväli, T. Rodima, V. Mäemets, I. Leito, I. A. Koppel. Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 p''K''<sub>a</sub> Units: Unification of Different Basicity Scales. ''J. Org. Chem.'', '''2005''', ''70'', 1019–1028. <sub>a</sub> value of protonated DBU) |
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| pKa = 13.5±1.5<ref name="Kaupmees_CCA">{{cite journal | author = Kaupmees, K. | author2 = Trummal, A. | author3 = Leito, I. | title = Basicities of Strong Bases in Water: A Computational Study | journal = Croat. Chem. Acta | year = 2014 | volume = 87 | issue = 4 | pages = 385–395 | doi = 10.5562/cca2472 | doi-access = free }}</ref> (p''K''{{sub|a}} of conjugate acid in water); 24.34<ref name="Kaljurand_2005_JOC">{{cite journal | author = Kaljurand, I. | author2 = Kütt, A. | author3 = Sooväli, L. | author4 = Rodima, T. | author5 = Mäemets, V. | author6 = Leito, I. | author7 = Koppel, I. A. | title = Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales | journal = J. Org. Chem. | year = 2005 | volume = 70 | issue = 3 | pages = 1019–1028 | doi = 10.1021/jo048252w | pmid=15675863}}</ref> (p''K''{{sub|a}} of conjugate acid in acetonitrile) |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = 119.9°C |
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| FlashPtC = 119.9 |
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| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}} |
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| RPhrases = R22 R34 |
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| GHSSignalWord = Danger |
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| SPhrases = S24 S25 |
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| HPhrases = {{H-phrases|301|302|312|314|412}} |
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}} |
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| PPhrases = {{P-phrases|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}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherCompounds = |
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'''1,8-Diazabicycloundec-7-ene''', or more commonly '''DBU''', is a ] and belongs to the class of ] compounds. It is used in ] as a ], a complexing ], and a ].<ref>{{cite journal|doi=10.1055/s-2004-815436|title=DBU (1,8-diazabicycloundec-7-ene) - A Nucleophillic Base|journal=Synlett|issue=3|pages=574–575|year=2004|last1=Ghosh|first1=Nandita|doi-access=free}}</ref> |
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==Occurrence== |
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Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge '']''.<ref name=Regalado>{{cite journal|author1=E. L. Regalado|author2=Judith Mendiola|author3=Abilio Laguna|author4=Clara Nogueiras|author5=Olivier P Thomas|journal=Nat. Prod. Commun.|year=2010|volume=5|title=Polar alkaloids from the Caribbean marine sponge ''Niphates digitalis''|issue=8 |pages=1187–1190 |pmid= 20839615}}</ref> The biosynthesis of DBU has been proposed to begin with ] and ]. |
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] |
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==Uses== |
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As a ] in organic chemistry, DBU is used as a ligand and base. As a base, protonation occurs at the imine nitrogen.<ref>{{cite journal | last1=Parviainen | first1=Arno | last2=King | first2=Alistair W. T. | last3=Mutikainen | first3=Ilpo | last4=Hummel | first4=Michael | last5=Selg | first5=Christoph | last6=Hauru | first6=Lauri K. J. | last7=Sixta | first7=Herbert | last8=Kilpeläinen | first8=Ilkka | title=Predicting Cellulose Solvating Capabilities of Acid–Base Conjugate Ionic Liquids | journal=ChemSusChem | volume=6 | issue=11 | date=2013 | issn=1864-5631 | doi=10.1002/cssc.201300143 | pages=2161–2169| pmid=24106149 | bibcode=2013ChSCh...6.2161P }}</ref> Lewis acids also attach to the same nitrogen.<ref>{{cite journal | last1=Romero | first1=Erik A. | last2=Zhao | first2=Tianxiang | last3=Nakano | first3=Ryo | last4=Hu | first4=Xingbang | last5=Wu | first5=Youting | last6=Jazzar | first6=Rodolphe | last7=Bertrand | first7=Guy | title=Tandem copper hydride–Lewis pair catalysed reduction of carbon dioxide into formate with dihydrogen | journal=Nature Catalysis | volume=1 | issue=10 | date=2018-10-01 | issn=2520-1158 | doi=10.1038/s41929-018-0140-3 | pages=743–747}}</ref> |
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These properties recommend DBU for use as a catalyst, for example as a ] for ] resins and ]. |
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It is used in the separation of ]s in conjunction with ]. It reacts with ] and higher fullerenes, but not with ]. |
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It is useful for ]s.<ref>{{cite book |doi=10.1002/047084289X.rd011.pub2 |chapter=1,8-Diazabicyclo[5.4.0]undec-7-ene |title=Encyclopedia of Reagents for Organic Synthesis |date=2006 |last1=Savoca |first1=Ann C. |last2=Urgaonkar |first2=Sameer |isbn=0-471-93623-5 }}</ref> |
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==See also== |
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* non-5-ene]] |
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* ] |
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==References== |
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<references/> |
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{{DEFAULTSORT:Diazabicycloundec-7-ene, 1, 8-}} |
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] |
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] |
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] |