Azobisisobutyronitrile

Chembox new
Name = AIBN
ImageFile = AIBN-2D-skeletal.png ImageName = The chemical structure of AIBN
ImageFile1 = AIBN-3D-vdW.png ImageName1 = 3D model of the AIBN molecule
IUPACName = 2,2′-Azobis(2-methylpropionitrile)
OtherNames = Azobisisobutyronitrile
Azobisisobutylonitrile
AIBN
Section1 = Chembox Identifiers
SMILES = N#CC(C)(C)N=NC(C)(C)C#N
CASNo = 78-67-1
Section2 = Chembox Properties
Formula = C₈H₁₂N₄
MolarMass = 164.21 g/mol
Appearance = white crystalline
Density = ?
Solubility = ?
MeltingPt = 103–105 °C
BoilingPt = °C
Section3 = Chembox Structure
Dipole = (gas)
Section7 = Chembox Hazards
ExternalMSDS =
EUClass =
FlashPt = ?

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:

:

These radicals can be used 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 [ [http://www2.dupont.com/Vazo/en_US/products/grades/grades.html Product Grades ] ] and Wako. [ [http://www.wako-chem.co.jp/specialty/waterazo/index.htm Water soluble Azo initiators ] ]

ee also

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

References