AIBN

(Azobisisobutyronitrile)

Other Names:

2,2'-Azobis(2-methylpropionitrile)

General Information:

Structure:

CAS Number: 78-67-1

Molecular Weight: 164.21 g/mol

Appearance: White crystals

Melting Point: 103-104 C

Azobisisobutyronitrile (AIBN) is a common reagent for the initiation of radical reactions. AIBN decomposes at temperatures above 60 C to form isobutyronitrile radicals, which function to initiate radical chemistry. Another very common radical intiator is benzoyl peroxide.

Common Uses:

Radical initiator in benzylic brominations

Procedure excerpt:

A mixture of the SM (100 g, 497 mmol), NBS (88.5 g, 497 mmol), and AIBN (10 g, 50 mmol) in CCl4 (700 mL) was stirred at reflux for 12 h. The mixture was cooled . . .

[full procedure]

Safety:

AIBN presents an explosion risk.

References:

1) Patent Reference: WO2016014463, page 101, (6.7 MB)

2) Pearson, A. J.; Roush, W. R.; Handbook of Reagents for Organic Synthesis; Activating Agents and Protecting Groups

3) Wikipedia: Azobisisobutyronitrile (link)

4) www.sigmaaldrich.com: 2,2'-Azobis(2-methylpropionitrile) (link)