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1972-28-7 - Diethyl azodicarboxylate, 97% - Azodicarboxylic acid diethyl ester - DEAD - L19348 - Alfa Aesar

L19348 Diethyl azodicarboxylate, 97%

Numéro CAS
1972-28-7
Synonymes
Azodicarboxylic acid diethyl ester
DEAD

Dimensions Prix ($) Quantité Disponibilité
5g 31,93
25g 88,68
100g 262,65
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Diethyl azodicarboxylate, 97%

MDL
MFCD00009103
EINECS
217-821-7

Propriétés chimiques

Formule
C6H10N2O4
Poids formulaire
174.16
Point d'ébullition
106°/13mm
Point d'éclair
85°(185°F)
Densité
1.106
Indice de réfraction
1.4210
Sensibilité
Air & Light Sensitive
Solubilité
Miscible with dichloromethane, diethyl ether and toluene.

Applications

Diethyl azodicarboxylate acts as a dienophile used in Diels-Alder reactions. It is used as a reagent in alfa-thiocyanation of enolizable ketones with ammonium thiocyanate and annulation of N-protected imines. It acts as a reactant for the preparation of immunostimulants alfa-Galactosylceramides, bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase and aza-beta-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes. It finds application in Mitsunobu reaction and used in the synthesis of pharmaceuticals like zidovudine and procarbazine. The presence of azo group in it is a Michael acceptor and used for the conversion of beta-ketoesters to the corresponding hydrazine derivatives in presence of copper(II) catalyst. Further, it is an efficient dehydrogenating agent, which is involved in the preparation of aldehydes, disulfides from alcohols and thiols respectively.

Notes

Store in a cool place. Incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents.

Références bibliographiques

Explosion risk by heating undiluted material.

Dehydrogenating agent and aza-dienophile. Oxidizes alcohols to aldehydes, thiols to disulfides and hydrazo to azo groups: J. Am. Chem. Soc., 88, 2328 (1966). Arylhydroxylamines are converted in high yield to nitroso compounds: Chem. Commun., 199 (1967).

Undergoes pericyclic reactions with alkenes and dienes via both ene and Diels-Alder processes. For further details and references, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 3, p. 1790.

Secondary and tertiary amines have been dealkylated by reaction with DEAD under mild conditions, followed by acid hydrolysis: J. Org. Chem., 38, 1652 (1973).

In combination with Triphenyl­phosphine, L02502 , is widely used in the Mitsunobu reaction for activation of primary and secondary alcohols by formation of the alkoxyphosphonium salts, which behave as versatile alkylating agents under mild SN2 conditions: reactions normally proceed with inversion of configuration. For reviews, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996); Synlett, 1221 (2003); Eur. J. Org. Chem., 2763 (2004):

For study of the mechanism, see: J. Org. Chem., 67, 1751 (2002).

Details for esterification of (-)-menthol with 4-nitrobenzoic acid with stereoinversion: Org. Synth. Coll., 9, 607 (1998). For an example of its use to convert a secondary alcohol to an amine by reaction with phthalimide followed by hydrazinolysis, see: Org. Synth. Coll., 7, 501 (1990). For dehydration of Boc-L-serine to the cyclic anhydride (2-oxetanone), see: Org. Synth. Coll., 9, 24 (1998).

ɑ-Amination of aldehydes can be effected in the presence of L-proline as an enantioselective catalyst, affording chiral ɑ-amino alcohols and ɑ-amino acids with good ee: Angew. Chem. Int. Ed., 41, 1790 (2002); for a similar reaction with scheme, see Dibenzyl­ azodicarboxyl­ate, L19347 .

See also Di-tert-butyl­ azodicarboxyl­ate, L00294 , and Diisopropyl­ azodicarboxyl­ate, L10386 .

Wang, Y.; Frett, B.; McConnell, N.; Li, H. Y. Metal-free, efficient hydrazination of imidazo[1,2-a]pyridine with diethyl azodicarboxylate in neutral media. Org. Biomol. Chem. 2015, 13 (10), 2958-2964.

Xu, N.; Li, D.; Zhang, Y.; Wang, L. Palladium-catalyzed direct ortho-ethoxycarbonylation of azobenzenes and azoxybenzenes with diethyl azodicarboxylate. Org. Biomol. Chem. 2015, 13 (34), 9083-9092.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H302-H312-H315-H319-H335-H227

Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Combustible liquid.

Mentions de prudence: P210-P261-P280-P305+P351+P338-P304+P340-P362-P301+P312-P312-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. 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. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
908662
Classe de danger
6.1
Groupe d'emballage
III
Code tarifaire harmonisé
2927.00
TSCA
No

Recommandé

  • A12124

    Diphenylphosphonic azide, 97%
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    1,8-Diazabicyclo[5.4.0]undec-7-ene, 99%
  • A14089

    Triphenylphosphine, flake, 99%
  • L10386

    Diisopropyl azodicarboxylate, 94%
  • 14112

    Triphenylphosphine, 99+%

Consulté récemment

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Analytique et matériel de laboratoire