Therefore, commercial shipment of pure diethyl azodicarboxylate is prohibited in the United States and is carried out either in solution or on polystyrene particles.
[4] DEAD is a strong electron acceptor and easily oxidizes a solution of sodium iodide in glacial acetic acid.
Photoassisted removal of hydrogen by DEAD was demonstrated for isopropyl alcohol, resulting in pinacol and tetraethyl tetrazanetetracarboxylate, and for acetaldehyde yielding diacetyl and diethyl hydrazodicarboxylate.
[4][13] DEAD is a reagent in the Mitsunobu reaction where it forms an adduct with phosphines (usually triphenylphosphine) and assists the synthesis of esters, ethers, amines and thioethers from alcohols.
[17][18][19] Another example of pharmaceutical application of DEAD-assisted Mitsunobu reaction is the synthesis of bis[(pivaloyloxy)methyl [PIVz] derivative of 2'-deoxy-5-fluorouridine 5'-monophosphate (FdUMP), which is a potent antitumor agent.
DEAD is an efficient component in Diels-Alder reactions and in click chemistry, for example the synthesis of bicyclo[2.1.0]pentane, which originates from Otto Diels.
[2][3][26] Shipment by air of pure diethyl azodicarboxylate is prohibited in the United States and is carried out in solution, typically about 40% DEAD in toluene.
[28] Safety hazards have resulted in rapid decline of DEAD usage and replacement with DIAD and other similar compounds.