DIAD

(Diisopropyl Azodicarboxylate)

Other Names:

Diisopropyl azodiformate

General Information:

Structure:

CAS Number: 2446-83-5

Molecular Weight: 202.21 g/mol

Melting Point: 3-5 C

Boiling Point: 75 C

Density: 1.027 g/mL

Diisopropyl azodicarboxylate (DIAD) is typically used for Mitsunobu reactions. Similar reagents to DIAD include DEAD, DtBAD, and ADDP. DIAD is quickly replacing Diethyl azodicarboxylate (DEAD) as the preferred azodicarboxylate due to the known safety concerns of DEAD.

Common Uses:

Reagent for Mitsunobu reactions

Procedure excerpt:

. . . in THF (7.6 mL). The mixture was cooled in an ice-H2O bath, then treated slowly with DIAD (0.41 mL, 2.1 mmol). The mixture was allowed to reach RT while stirring . . .

[full procedure]

References:

1) Patent Reference: WO2016011390, page 469, (20.2 MB)

2) Wikipedia: Diisopropyl azodicarboxylate (link)

3) www.sigmaaldrich.com: Diisopropyl azodicarboxylate (link)