Consentement d'utilisation des Cookies

J'accepte. Notre site sauvegarde des traceurs textes (cookies) sur votre appareil afin de vous garantir de meilleurs contenus et à des fins de collectes statistiques.Vous pouvez désactiver l'usage des cookies en changeant les paramètres de votre navigateur. En poursuivant votre navigation sur notre site sans changer vos paramètres de navigateur vous nous accordez la permission de conserver des informations sur votre appareil.

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%

Numéro de CAS
280-57-9
Synonymes
Dabco
TEDA

Conditionnement Prix ($) Quantité Disponibilité
25g 21,30
100g 45,10
500g 124,00
Ajouter au panier Ajouter au devis en vrac Afficher l'article

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

MDL
MFCD00006689
EINECS
205-999-9

Propriétés chimiques

Formule
C6H12N2
Poids moleculaire
112.17
Point de fusion
155-160°
Point d'ébullition
174-176°
Point d'éclair
62°(143°F)
Densité
1.140
Sensibilité
Hygroscopic
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H228-H302-H315-H318-H335

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

Mentions de prudence: 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.

Autres références

Merck
14,9669
Beilstein
103618
Classe de danger
3
Groupe d'emballage
II
Code tarifaire harmonisé
2933.59
TSCA
Yes
RTECS
HM0354200

Recommandé

Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux

Catalyseurs

Analytique et matériel de laboratoire