Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

A14003 1,4-Diazabicyclo[2.2.2]octane, 98%

CAS Number

Stock No. Size Price ($) Quantity Availability
A14003-14 25g 22.10
A14003-22 100g 47.20
A14003-36 500g 134.00
Add to Cart Add to Quote Request View Item

1,4-Diazabicyclo[2.2.2]octane, 98%


Chemical Properties

Formula Weight
Melting point
Boiling Point
Flash Point
Storage & Sensitivity
Hygroscopic. Ambient temperatures.
Soluble in water, acetone, benzene, ethanol and methyl ethyl ketone.


1,4-Diazabicyclo[2.2.2]octane is used as polyurethane catalyst, Balis-Hillman reaction catalyst complexing ligand and lewis base. It finds use in dye lasers and in mounting samples for fluorescence microscopy and as anti-fade reagent shown to scavenge free radicals due to flurochrome excitation of fluorochromes. Further, it is an oxidation and polymerization catalyst.


Hygroscopic. Incompatible with strong oxidizing agents and strong acids.

Literature References

Dabco is a registered trademark of Air Products and Chemicals Inc.

Forms crystalline complexes with organolithium compounds: J. Am. Chem. Soc., 87, 3276 (1965), which show enhanced reactivity, e.g. in the high yield ɑ-metallation of thioanisole by n-BuLi: J. Org. Chem., 31, 4097 (1966).

Forms a stable crystalline complex with H2O2, useful as an equivalent to "anhydrous" H2O2: reaction with TMS chloride gives bis(TMS) peroxide, a useful OH+-equivalent, e.g. in the conversion of aryllithiums to phenols: Synthesis, 633 (1986).

Catalyzes the addition of aldehydes to Michael acceptors at the ɑ-position (Baylis-Hillman reaction): Helv. Chim. Acta, 63, 413 (1984):

For further illustrative example, see: Org. Synth., 75, 106 (1997). Complete reaction often takes several days at ambient temperature, while heating causes lower yields. However, it is greatly accelerated by microwave irradiation: Synlett, 444 (1994). Superior results with reduced reaction times can be achieved in aqueous medium: J. Org. Chem., 66, 5413 (2001). The use as reaction medium of tetramethylene sulfone: Tetrahedron Lett., 45, 1183 (2004), or PEG-400: Tetrahedron Lett., 45, 5865 (2004) has also been advocated. Lithium perchlorate was found to increase the reaction rate dramatically: Tetrahedron Lett., 40, 1539 (1999), as was a catalytic amount of a metal triflate, particularly La or Sm; conventional Lewis acids were ineffective: J. Org Chem., 63, 7183 (1998). For asymmetric Baylis-Hillman reaction using (1S,2R)-(-)-10,2-Camphorsultam, A15897, as chiral auxiliary, see: J. Am. Chem. Soc., 119. 4317 (1997). See also 3-Quinuclidinol, B21503. For more recent discussion and comparison of different catalysts, see: J. Org. Chem., 692 (2003). In a reinterpretaion of the mechanism, a hemiacetal interemediate has been proposed: J. Org. Chem., 70, 3980 (2005). For reviews of the Baylis-Hillman reaction, see: Tetrahedron, 44, 4653 (1988); 52, 8001 (1996).

Promotes the cleavage of ß-keto esters in refluxing xylene directly to ketones, without the need for prior hydrolysis: J. Org. Chem., 39, 1592, 2647 (1974). Similarly, malonic esters can be cleaved to esters of substituted acetic acids: J. Org. Chem., 41, 208 (1976).

In conjunction with palladium acetate and PEG-400 provides a reusable catalyst system for the Suzuki-Miyaura cross-coupling reaction of boronic acids: J. Org. Chem., 70, 5409 (2005).

Lu, W.; Zhang, G.; Li, J.; Hao, J.; Wei, F.; Li, W.; Zhang, J.; Shao, Z. G.; Yi, B. Polybenzimidazole-crosslinked poly(vinylbenzyl chloride) with quaternary 1,4-diazabicyclo (2.2.2) octane groups as high-performance anion exchange membrane for fuel cells. J. Power Sources 2015, 296, 204-214.

Yarinich, L. A.; Burakova, E. A.; Zakharov, B. A.; Boldyreva, E. V.; Babkina, I. N.; Tikunova, N. V.; Silnikov, V. N. Polybenzimidazole-crosslinked poly(vinylbenzyl chloride) with quaternary 1,4-diazabicyclo (2.2.2) octane groups as high-performance anion exchange membrane for fuel cells. Eur. J. Med. Chem. 2015, 95, 563-573.

GHS Hazard and Precautionary Statements

Hazard Statements: H228-H302-H315-H318-H335

Flammable solid. Harmful if swallowed. Causes skin irritation. Causes serious eye damage. May cause respiratory irritation.

Precautionary Statements: P210-P261-P280a-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Hazard Class
Packing Group
Harmonized Tariff Code


Recently Viewed


Life Science

Metals & Materials


Analytical & Labware