DABCO: Difference between revisions

| verifiedrevid = 443556150

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageFileL1 = Dabco.gif

| ImageSizeL1 = 105 px

| ImageFileR1 = DABCO-3D-balls.png

| ImageSizeR1 = 150 px

| IUPACName = 1,4-diazabicyclo[2.2.2]octane

| OtherNames = triethylenediamine, TEDA<br>DABCO

| Section1 = {{Chembox Identifiers

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

| ChemSpiderID = 8882

| InChI = 1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2

| InChIKey = IMNIMPAHZVJRPE-UHFFFAOYSA-N

| InChI1 = 1/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2

| InChIKey1 = IMNIMPAHZVJRPE-UHFFFAOYAP

| SMILES1 = N12CCN(CC1)CC2

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 280-57-9

| PubChem = 9237

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = IMNIMPAHZVJRPE-UHFFFAOYSA-N

| SMILES = C1CN2CCN1CC2

| Formula = C₆H₁₂N₂

| MolarMass = 112.17 g/mol

| Appearance = White crystalline powder

| Density =

| MeltingPt = 156 - 160 °C

| BoilingPt = 174 °C

| Solubility = Soluble, hygroscopic

}}

| Section3 = {{Chembox Hazards

| MainHazards = Harmful

| FlashPt =

| Autoignition =

| RPhrases = {{R11}} {{R22}} {{R36}} {{R37}} {{R38}} {{R52}} {{R53}}

| Reference = <ref>{{cite web | url = http://physchem.ox.ac.uk/MSDS/DI/1,4-diazabicyclo(2.2.2)octane.html | title = Safety data for 1,4-diazabicyclo(2.2.2)octane | publisher = [[Oxford University]]}}</ref>

}}

'''DABCO''' or '''1,4-diazabicyclo[2.2.2]octane''' is a [[chemical compound]]. It is a [[polyurethane]] and [[Baylis-Hillman reaction]] [[catalyst]], complexing [[ligand]] and [[Lewis acids and bases|Lewis base]].<ref>{{cite journal |author=Luca Cecchi1, Francesco De Sarlo, Fabrizio Machetti |title=1,4-Diazabicyclo[2.2.2]octane (DABCO) as an Efficient Reagent for the Synthesis of Isoxazole Derivatives from Primary Nitro Compounds and Dipolarophiles: The Role of the Base |journal=Eur. J. Org. Chem. |volume=2006 |issue=21 |pages=4852–4860 |year=2006 |month=August |doi=10.1002/ejoc.200600475}}</ref> It is used to regulate the reaction rate in [[Flexplay]] time-limited [[DVD]]s by adjusting pH. Antioxidants, like DABCO, are used to improve the lifetime of [[dye]]s. This makes DABCO useful in [[dye laser]]s and in mounting samples for [[fluorescence microscopy]] (when used with [[glycerol]] and [[Phosphate buffered saline|PBS]]).<ref>{{cite journal |author=Valnes K, Brandtzaeg P |title=Retardation of immunofluorescence fading during microscopy |journal=J. Histochem. Cytochem. |volume=33 |issue=8 |pages=755–61 |year=1985 |month=August |pmid=3926864 |doi= |url=http://www.jhc.org/cgi/pmidlookup?view=long&pmid=3926864}}</ref> DABCO can also be used to demethylate quaternary ammonium salts by heating in [[N,N-dimethylformamide]] (DMF).<ref>{{cite journal | author = Ho, T.L | journal = [[Synthesis (journal)|Synthesis]] | year = 1972 | pages = 702 | doi = 10.1055/s-1972-21977 | title = Dealkylation of Quaternary Ammonium Salts with 1,4-Diazabicyclo[2.2.2]octane | volume = 1972 | issue = 12}}</ref>

DABCO has been used as a catalyst for a metal-free [[Sonogashira coupling]], with or without microwave enhancement.<ref name="Luque2009">{{cite journal|last=Luque|first=Rafael|coauthors=Duncan J Macquarrie|year=2009|title=Efficient solvent- and metal-free Sonogashira protocol catalysed by 1,4-diazabicyclo(2.2.2) octane (DABCO)|journal=[[Organic and Biomolecular Chemistry]]|publisher=Royal Society of Chemistry|volume=7|pages=1627–1632|doi=10.1039/b821134p|pmid=19343249|issue=8}}</ref> For example, [[phenylacetylene]] couples with electron-deficient iodoarenes to furnish the Sonogashira product in 77% yield with 95% selectivity.

:[[File:DABCO Sonogashira.png|500px|Example of a DABCO-catalysed Sonogashira coupling]]

Dabco is a registered trademark for [[Air Products]]' catalyst product line including 1,4-diazabicyclo[2.2.2]octane.

== References ==

[[Category:Amines]]

[[Category:Nitrogen heterocycles]]

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