Diethyl Azodicarboxylate Properties, Molecular Formula, Applications - WorldOfChemicals

Diethyl Azodicarboxylate Properties

Diethyl Azodicarboxylate

Diethyl Azodicarboxylate 3D Structure-Molecule 3D Struture
Molecule 3D Structure Image
Diethyl Azodicarboxylate Structure-Molecule Struture
Molecule Structure Image

Description

 

Diethyl azodicarboxylate is an organic compound. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating. Therefore, commercial shipment of pure diethyl azodicarboxylate is prohibited in the United States and is carried out either in solution or on polystyrene particles. It is an aza-dienophile and an efficient dehydrogenating agent, converting alcohols to aldehydes, thiols to disulfides and hydrazo groups to azo groups; it is also a good electron acceptor. While DEAD is used in numerous chemical reactions, it is mostly known as the principal component of the Mitsunobu reaction, which is daily carried out in chemical laboratories, and can be used for the synthesis of various natural products and pharmaceuticals. In particular, the resulting chemical zidovudine is a major drug against AIDS and FdUMP is a potent antitumor agent.

Chemical Properties

Appearance Clear Orange to Orange-Red Liquid
Boiling Point 104.5 °C
CAS Number 1972-28-7
Class 6.1
Density 1.11 g/cm3
EINECS Number 217-821-7
IUPAC Name Diethyl Diazenedicarboxylate
InChI 1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+
InChIKey FAMRKDQNMBBFBR-BQYQJAHWSA-N
Melting Point 6 °C
Molar Mass 174.15 g/mol
Molecular Formula C6H10N2O4
NFPA 704 H-1,F-1,R-0,C-NA
PG 3
Refractive n20/D 1.47
Synonyms Diethyl 1,2-diazenedicarboxylate;Diethyl Azidoformate;1,2-Diazenedicarboxylicacid, 1,2-diethyl ester;Diazenedicarboxylicacid, Diethyl Ester;Formic acid, azodi-, diethyl ester;1,2-Ethoxycarbonyl Diazene;Azodicarboxylic Acid Diethyl Ester;DEAD;Diethoxycarbonyldiazene;Diethyl Azodicarboxylate;Diethyl Diazenedicarboxylate;Diethyl Diazodicarboxylate;NSC 3474;NSC 679015;Unifoam AZ-AE 200