Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 1,8-Diazabicyclo(5.4.0)undec-7-ene: Difference between pages

{{short description|Chemical compound}}

{{correct title|reason=bracket|title=1,8-Diazabicyclo[5.4.0]undec-7-ene}}

| Watchedfields = changed

| verifiedrevid = 477206737

| Name = 1,8-Diazabicyclo[5.4.0]undec-7-ene

| ImageFile = DBU.svg

| ImageName =

| ImageFile1 = DBU-3D-balls.png

| ImageAlt1 = DBU molecule

| PIN = 2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-''a'']azepine

| OtherNames = DBU, Diazabicycloundecene

|Section1={{Chembox Identifiers

| SMILES = N\2=C1\N(CCCCC1)CCC/2

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| PubChem = 81184

| EC_number = 229-713-7

| UNII = H1ILJ6IBUX

| RTECS =

|Section2={{Chembox Properties

| C=9|H=16|N=2

| Appearance = Colorless liquid

| Density = 1.018 g/mL liquid

| Solubility = ethers, alcohols

| MeltingPtC = -70

| BoilingPtC = 261

| BoilingPt_notes = (1 atm),<br/>80 to 83 °C (0.6 mmHg)

| 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&ndash;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&ndash;1028 | doi = 10.1021/jo048252w | pmid=15675863}}</ref> (p''K''{{sub|a}} of conjugate acid in acetonitrile)

| Viscosity =

|Section7={{Chembox Hazards

| ExternalSDS =

| MainHazards =

| FlashPtC = 119.9

| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|301|302|312|314|412}}

| 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}}

|Section8={{Chembox Related

| OtherCompounds =

}}

'''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]].<ref>{{cite journal|doi=10.1055/s-2004-815436|title=DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) - A Nucleophillic Base|journal=Synlett|issue=3|pages=574–575|year=2004|last1=Ghosh|first1=Nandita|doi-access=free}}</ref>

==Occurrence==

Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge ''[[Niphates digitalis]]''.<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 [[adipaldehyde]] and [[1,3-diaminopropane]].

[[File:REGALADO DBU BIOSYNTHETIC HYPOTHESIS.png|500px|center|thumb|Proposed pathway for the biosynthesis of DBU in sponges.<ref name=Regalado/>]]

==Uses==

As a [[reagent]] in organic chemistry, DBU is used as a ligand and base. As a base, protonation occurs at the imine nitrogen.<ref>{{cite journal | last=Parviainen | first=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}}</ref> Lewis acids also attach to the same nitrogen.<ref>{{cite journal | last=Romero | first=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>

These properties recommend DBU for use as a catalyst, for example as a [[curing agent]] for [[epoxy]] resins and [[polyurethane]].

It is used in the separation of [[fullerene]]s in conjunction with [[1,2,4-Trimethylbenzene|trimethylbenzene]]. It reacts with [[C70 fullerene|C₇₀]] and higher fullerenes, but not with [[Buckminsterfullerene|C₆₀]].

It is useful for [[dehydrohalogenation]]s.<ref>{{cite book |doi=10.1002/047084289X.rd011.pub2 |chapter=1,8-Diazabicyclo&#91;5.4.0&#93;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>

==See also==

* [[1,5-Diazabicyclo(4.3.0)non-5-ene|1,5-Diazabicyclo[4.3.0]non-5-ene]]

* [[DABCO]]

==References==

<references/>

{{DEFAULTSORT:Diazabicycloundec-7-ene, 1, 8-}}

[[Category:Amidines]]

[[Category:Reagents for organic chemistry]]

[[Category:Non-nucleophilic bases]]