Diethyl Azodicarboxylate

Abstract

[1972-28-7] C6H10N2O4 (MW 174.16) InChI = 1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3 InChIKey = FAMRKDQNMBBFBR-UHFFFAOYSA-N (functional group oxidations;5 dealkylation of mines;16 enophile;24 dienophile33) Alternate Names: diethyl azidoformate; DEAD; DAD.2 Physical Data: bp 108––110 °C/15 mmHg; bp 211 °C/760 mmHg; fp 110 °C, d 1.11 g cm−3. Solubility: sol CH2Cl2, Et2O, toluene. Form Supplied in: orange liquid; 90% (technical grade) and 95% purity are commonly available, as is a 40% solution in toluene. Preparative Method: although widely available, diethyl azodicarboxylate can be readily prepared from ethyl chloroformate and hydrazine, followed by oxidation of the resulting diethyl hydrazodicarboxylate.3 Purification: in most cases commercial samples are used without purification. Distillation is possible, but not recommended. Handling, Storage, and Precautions: flammable; may produce toxic combustion by-products. Heat and light sensitive; should be stored in dark containers under refrigerated conditions. These containers should also be vented periodically to reduce pressure. DAD has been reported to occasionally decompose violently when heated.3a,4 Use in a fume hood.