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

L19348 Diethyl azodicarboxylate, 97%

Codice CAS
1972-28-7
Sinonimi
Azodicarboxylic acid diethyl ester
DEAD

Dimensioni Prezzo ($) Quantità Disponibilità
5g 32,20
25g 89,50
100g 265,00
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Diethyl azodicarboxylate, 97%

MDL
MFCD00009103
EINECS
217-821-7

Proprietà chimiche

Formula
C6H10N2O4
Peso formula
174.16
Punto di ebollizione
106°/13mm
Punto di infiammabilità
85°(185°F)
Densità
1.106
Indice di rifrazione
1.4210
Sensibilità
Air & Light Sensitive
Solubilità
Miscible with dichloromethane, diethyl ether and toluene.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H227-H302-H312-H315-H319-H335

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

Dichiarazioni precauzionali: P210u-P261-P280-P305+P351+P338-P405-P501a

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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
908662
Classe di rischio
6.1
Gruppo di imballaggio
III
Codice tariffe armonizzato
2927.00
TSCA
No

Raccomandato

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  • A14089

    Triphenylphosphine, flake, 99%
  • L10386

    Diisopropyl azodicarboxylate, 94%
  • 14112

    Triphenylphosphine, 99+%

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