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280-57-9 - 1,4-Diazabicyclo[2.2.2]octane, 98% - Dabco - TEDA - A14003 - Alfa Aesar

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

CAS-Nummer
280-57-9
Synonyme
Dabco
TEDA

Größe Preis ($) Menge Verfügbarkeit
25g 18,54
100g 44,91
500g 123,60
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

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

MDL
MFCD00006689
EINECS
205-999-9

Chemische Eigenschaften

Formel
C6H12N2
Molmasse
112.17
Schmelzpunkt
155-160°
Siedepunkt
174-176°
Flammpunkt
62°(143°F)
Dichte
1.140
Sensitivität
Hygroscopic
Löslichkeit
Soluble in water, acetone, benzene, ethanol and methyl ethyl ketone.

Anwendungen

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.

Bemerkungen

Hygroscopic. Incompatible with strong oxidizing agents and strong acids.

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H228-H318-H315-H302-H335

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

Sicherheitshinweise: P210-P261-P280-P240-P305+P351+P338-P304+P340-P310-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Merck
14,9669
Beilstein
103618
Gefahrenklasse
3
Verpackungsgruppe
II
Harmonized Tariff Code
2933.59
TSCA
Yes
RTECS
HM0354200

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