Diethyl azodicarboxylate

Diethyl azodicarboxylate

Names
IUPAC name Diethyl diazenedicarboxylate
Other names Diethyl azidoformate, Diazenedicarboxylic acid, Diethyl azo diformate
Identifiers
CAS Number	1972-28-7 Y
3D model (Jmol)	Interactive image
ChemSpider	4510444 Y
PubChem	220568
InChI InChI=1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+ Y Key: FAMRKDQNMBBFBR-BQYQJAHWSA-N Y InChI=1/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+ Key: FAMRKDQNMBBFBR-BQYQJAHWBW
SMILES O=C(/N=N/C(=O)OCC)OCC
Properties
Chemical formula	C6H10N2O4
Molar mass	174.16 g·mol−1
Appearance	Orange to red to orange liquid
Density	1.11 g/cm3
Melting point	6 °C (43 °F; 279 K)
Boiling point	104.5 °C (220.1 °F; 377.6 K) at 12 mm Hg
Refractive index (nD)	1.420 (20 °C)
Hazards
Safety data sheet	External MSDS
R-phrases	R20 R21 R22 R36 R37 R38 R40 R44
S-phrases	S15 S23 S26 S36
Flash point	85 °C (185 °F; 358 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT, is an organic compound with the structural formula CH₃CH₂O₂CN=NCO₂CH₂CH₃. 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.

DEAD 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, also procarbazine, a nonreversible MAOI.

DEAD is an orange-red liquid which weakens its color to yellow or colorless upon dilution or chemical reaction. This color change is conventionally used for visual monitoring of the synthesis. DEAD dissolves in most common organic solvents, such as toluene, chloroform, ethanol,tetrahydrofuran and dichloromethane but has low solubility in water or carbon tetrachloride; the solubility in water is higher for the related azo compound dimethyl azodicarboxylate.