Azobisisobutyronitrile

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AIBN
AIBN-2D-skeletal.png
AIBN-3D-vdW.png
IUPAC name 2,2′-Azobis(2-methylpropionitrile)
Other names Azobisisobutyronitrile
Azobisisobutylonitrile
AIBN
Identifiers
CAS number 78-67-1
SMILES N#CC(C)(C)N=NC(C)(C)C#N
Properties
Molecular formula C8H12N4
Molar mass 164.21 g/mol
Appearance white crystalline
Density  ?
Melting point

103–105 °C

Boiling point

°C

Solubility in water  ?
Structure
Dipole moment (gas)
Hazards
Flash point  ?
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


Overview

Azobisisobutyronitrile is a toxic compound often used as a foamer in plastics and rubber and as a radical initiator. It is commonly known as AIBN. Its most common chemical reaction is one of decomposition, eliminating a molecule of nitrogen gas to form two 2-cyanoprop-2-yl radicals:

AIBN-radical-2D.png

These radicals can be used to to initiate free radical polymerizations and other radical reactions. For instance a mixture of styrene and maleic anhydride in toluene will react if heated, forming the polystyrene polymer, only very slowly unless an initiator such an AIBN is present. Another example of a radical reaction that can be initiated by AIBN is the anti-Markovnikov hydrohalogenation of alkenes.

AIBN is safer to use than benzoyl peroxide (another radical initiator) because the risk of explosion is far smaller. However, it is considered a flammable solid. It is soluble in methanol and ethanol, but is insoluble in water. It can explode if dissolved in acetone. AIBN is highly toxic. Wear a respirator/dust mask, protective gloves, & safety glasses when handling AIBN.

Several water-soluble azo initiators similar to AIBN are manufactured by DuPont[1] and Wako.[2]

See also

  • 1,1'-Azobis(cyclohexanecarbonitrile) or ABCN is another free radical initiator

References

  1. Product Grades
  2. Water soluble Azo initiators


de:Azo-bis-(isobutyronitril)


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