DABCO or 1,4-diazabicyclo[2.2.2]octane is a chemical compound and a registered trademark for Air Products' catalyst product line including 1,4-diazabicyclo[2.2.2]octane. It is a polyurethane catalyst, Baylis-Hillman reaction catalyst, complexing ligand, and Lewis base. 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). DABCO can also be used to demethylate quaternary ammonium salts by heating in dimethylformamide (DMF).Although the first pKa is 8.8 that is almost the same as ordinary alkylamines, the nucleophilicity is high because the alkyl groups does not disturb the lone pairs.DABCO has been used as a catalyst for a metal-free Sonogashira coupling, with or without microwave enhancement. For example, phenylacetylene couples with electron-deficient iodoarenes to furnish the Sonogashira product in 77% yield with 95% selectivity.
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