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Diethyl azodicarboxylate

CAS No.:1972-28-7
Molecular Weight: 174.15500 Molecular Formula: C6H10N2O4

Description

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.

Properties

Appearance:red to orange liquid
Density:1.106
Melting Point:
Boiling Point:106ºC (13 mmHg)
Storage temp:2-8ºC
Vapour:0.589mmHg at 25°C
Refractive Index:n20/D 1.47
Flash Point:106.9ºC
Solubility:
Stability:Stable, but may explode if heated under confinement. May be shock sensitive. Decomposes vigorously if heated above 100ºC. Incompatible with strong acids, strong bases, strong oxidizing agents, strong reducing agents. Light sensitive.

Safety and Handling

RTECS:UN 3233

Hazard Class:III

Safety Statements:S26-S36/37-S62

HS Code:2927000090

Packing Group:III

WGK Germany:3

RIDADR:UN 3233

Risk Statements:R5; R11; R20; R36/37/38; R48/20; R63; R65; R67

Hazard Codes:F; Xn

Signal Word:Danger

Symbol:GHS02, GHS07, GHS08

Caution Statement:P261; P281; P301 + P310; P305 + P351 + P338; P331

Hazard Declaration:H226; H242; H304; H315; H319; H335 + H336; H361d; H373

NMR Spectrum