Diethyl azodiformate

Diethyl azodicarboxylate

Molecular formula: (C2H5OOCN)2

Molecular weight: 174.16

CAS No.: 1972-28-7

Hazardous material labels: F, Xn, Xi

Safety Terms: 26-36/37-62-47-36-35

Risk terms: F, Xn, Xi

【Introduction】
Melting point: 6℃

Boiling point: 106℃ (13 mmHg)

Density: 1.106

Refractive index: n20/D 1.47

Flash point: 85℃

Storage conditions: 2-8℃

Solubility: Miscible with dichloromethane, diethyl ether, and toluene

Sensitivity: Air Sensitive BRN 908662

Stability: Stable, but may explode when heated under confinement. May be shock-sensitive. Decomposes vigorously at temperatures above 100℃. Incompatible with strong acids, strong bases, strong oxidizing agents, and strong reducing agents. Light-sensitive.

【Application】
1. DEAD and triphenylphosphine are reagents in the Mitsunobu reaction (Mitsunobu reaction), where DEAD serves as the
active reagent acting as a hydrogen acceptor, while triphenylphosphine functions as an oxygen acceptor, forming high-energy P=O bonds after the reaction.

2. DEAD can also act as a dienophile in Diels-Alder reactions with conjugated dienes to form [4+2] adducts. When the
diene component is an aryl vinyl group, it can be used for the synthesis of fused tetrahydrodiazepines. The resulting
adducts can further undergo alkaline hydrolysis, decarboxylation, oxidation to azo compounds using copper chloride, and
subsequent alkaline treatment to yield cyclized products.

3. The DEAD reaction with conjugated dienes, specifically the Ene reaction and the Diels-Alder reaction, are
competitive reactions. However, under normal circumstances, one of the two products is the absolute major product. The
reason for this phenomenon remains unclear.

4. DEAD is a Michael addition acceptor. Under copper salt catalysis, it reacts with β-keto esters to yield hydrazine
derivatives.