DABCO

DABCO
DABCO
Identifiers
CAS number 280-57-9 YesY
PubChem 9237
ChemSpider 8882 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C6H12N2
Molar mass 112.17 g/mol
Appearance White crystalline powder
Melting point

156 - 160 °C

Boiling point

174 °C

Solubility in water Soluble, hygroscopic
Hazards[1]
R-phrases R11 R22 R36 R37 R38 R52 R53
Main hazards Harmful
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 base.[2] It is used to regulate the reaction rate in Flexplay time-limited DVDs by adjusting pH. Antioxidants, like DABCO, are used to improve the lifetime of dyes. This makes DABCO useful in dye lasers and in mounting samples for fluorescence microscopy (when used with glycerol and PBS).[3] DABCO can also be used to demethylate quaternary ammonium salts by heating in N,N-dimethylformamide (DMF).[4]

DABCO has been used as a catalyst for a metal-free Sonogashira coupling, with or without microwave enhancement.[5] For example, phenylacetylene couples with electron-deficient iodoarenes to furnish the Sonogashira product in 77% yield with 95% selectivity.

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

  1. ^ "Safety data for 1,4-diazabicyclo(2.2.2)octane". Oxford University. http://physchem.ox.ac.uk/MSDS/DI/1,4-diazabicyclo(2.2.2)octane.html. 
  2. ^ Luca Cecchi1, Francesco De Sarlo, Fabrizio Machetti (August 2006). "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". Eur. J. Org. Chem. 2006 (21): 4852–4860. doi:10.1002/ejoc.200600475. 
  3. ^ Valnes K, Brandtzaeg P (August 1985). "Retardation of immunofluorescence fading during microscopy". J. Histochem. Cytochem. 33 (8): 755–61. PMID 3926864. http://www.jhc.org/cgi/pmidlookup?view=long&pmid=3926864. 
  4. ^ Ho, T.L (1972). "Dealkylation of Quaternary Ammonium Salts with 1,4-Diazabicyclo[2.2.2]octane". Synthesis 1972 (12): 702. doi:10.1055/s-1972-21977. 
  5. ^ Luque, Rafael; Duncan J Macquarrie (2009). "Efficient solvent- and metal-free Sonogashira protocol catalysed by 1,4-diazabicyclo(2.2.2) octane (DABCO)". Organic and Biomolecular Chemistry (Royal Society of Chemistry) 7 (8): 1627–1632. doi:10.1039/b821134p. PMID 19343249. 

Wikimedia Foundation. 2010.

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

  • DABCO — ®: Marke für ↑ Diazabicyclooctan …   Universal-Lexikon

  • DABCO — Strukturformel Allgemeines Name DABCO Andere Namen 1,4 Diazabic …   Deutsch Wikipedia

  • 1,4-diazabicyclo(2.2.2)octane — 1,4 diazabicyclo[2.2.2]octane Général …   Wikipédia en Français

  • Baylis-Hillman reaction — The Baylis Hillman reaction is an organic reaction of an aldehyde and an α,β unsaturated electron withdrawing group catalyzed by DABCO (1,4 diazabicyclo [2.2.2] octane) to give an allylic alcohol [Baylis, A. B.; Hillman, M. E. D. German Patent… …   Wikipedia

  • Reacción de Baylis-Hillman — Saltar a navegación, búsqueda La reacción de Baylis Hillman es una reacción orgánica de un aldehído y un compuesto orgánico insaturado con un grupo atractor de electrones, catalizada por DABCO (1,4 diazabiciclo[2.2.2]octano) para producir un… …   Wikipedia Español

  • Baylis–Hillman reaction — The Baylis–Hillman reaction is an organic reaction of an aldehyde and an α,β unsaturated electron withdrawing group catalyzed by DABCO (1,4 diazabicyclo[2.2.2]octane) to give an allylic alcohol.[1][2] This reaction is also known as the… …   Wikipedia

  • Triethylendiamin — Strukturformel Allgemeines Name Triethylendiamin Andere Namen 1,4 Diazabicyclo[2.2.2]octan ( …   Deutsch Wikipedia

  • Schutzgruppe — Mit der Butyloxycarbonyl Gruppe an der Aminogruppe geschützte α Aminosäure Glycin. Die Boc Schutzgruppe ist blau markiert …   Deutsch Wikipedia

  • Baylis-Hillman-Reaktion — Die Baylis Hillman Reaktion, manchmal auch als Morita Baylis Hillman Reaktion bezeichnet, ist eine Reaktion aus dem Bereich der Organischen Chemie und wurde nach ihren Entdeckern Anthony B. Baylis und Melville E. D. Hillman benannt. Sie dient der …   Deutsch Wikipedia

  • Chemikalienliste — Die Chemikalienliste stellt eine alphabetisch sortierte Liste von Chemikalien dar, ohne Anspruch auf Vollständigkeit. Elemente sind fett gekennzeichnet, Stoffgruppen kursiv. Der Haupteintrag zu einer Chemikalie ist gleichzeitig der Name des… …   Deutsch Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”