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Diethyl azodicarboxylate, often abbreviated DEAD, is the organic compound CH3CH2O2CN=NCO2CH2CH3. As indicated with this formula, the molecule consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This red orange liquid is a valuable reagent but also quite dangerous.
Additional recommended knowledge
Although widely available, diethyl azodicarboxylate can be prepared in the laboratory. A two-step synthesis starts from hydrazine, first by alkylation with ethyl chloroformate. followed by treating the resulting ethyl hydrazodicarboxylate with chlorine.
Red fuming nitric acid can also be used in the second step.
DEAD is toxic, shock sensitive, and thermally unstable. It is handled as a solution, rarely as the pure compound. This safety hazards have resulted in DEAD usage rapidly declining and being replaced with DIAD (Diisopropyl azo dicarboxylate).
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Diethyl_azodicarboxylate". A list of authors is available in Wikipedia.|