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

CAS Number
280-57-9
Synonyms
Dabco
TEDA

Stock No. Size Price ($) Quantity Availability
A14003-14 25g 22.10
A14003-22 100g 47.20
A14003-36 500g 134.00
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1,4-Diazabicyclo[2.2.2]octane, 98%

MDL
MFCD00006689
EINECS
205-999-9

Chemical Properties

Formula
C6H12N2
Formula Weight
112.17
Melting point
155-160°
Boiling Point
174-176°
Flash Point
62°(143°F)
Density
1.140
Storage & Sensitivity
Hygroscopic. Ambient temperatures.
Solubility
Soluble in water, acetone, benzene, ethanol and methyl ethyl ketone.

Applications

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.

Notes

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-H500

Flammable solid. Harmful if swallowed. Causes skin irritation. Causes serious eye damage. May form combustible dust concentrations in air

Precautionary Statements: P210-P240-P241-P264b-P270-P280-P301+P312-P302+P352-P305+P351+P338-P310-P330-P332+P313-P362-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,9669
Beilstein
103618
Hazard Class
4.1
Packing Group
II
Harmonized Tariff Code
2933.59
TSCA
Yes
RTECS
HM0354200

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