Diethyl azodicarboxylate,C6H10N2O4,CAS 1972-28-7
|Synonyms||Azodicarboxylic acid diethyl ester, DEAD|
|Sensitivity||Air & Light Sensitive|
|Solubility||Miscible with dichloromethane, diethyl ether and toluene|
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.
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Store in a cool place. Incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents.
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