| Revision as of 20:29, 26 May 2011 editChemNerd (talk | contribs)Extended confirmed users17,568 edits added Category:Radical initiators using HotCat← Previous edit | Revision as of 20:40, 26 May 2011 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - updated 'ImageFile_Ref', 'UNII_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Misplaced PagesNext edit → | ||
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| | verifiedrevid = 396294932 | | verifiedrevid = 396294932 | ||
| | Name = AIBN | | Name = AIBN | ||
| | ImageFile_Ref = {{chemboximage|correct|??}} | |||
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| ImageFile = AIBN Structural Formulae.png | ||
| | ImageName = The chemical structure of AIBN | | ImageName = The chemical structure of AIBN | ||
| | ImageFile1 = AIBN-3D-vdW.png | | ImageFile1 = AIBN-3D-vdW.png | ||
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| | PubChem = 6547 | | PubChem = 6547 | ||
| | InChIKey = OZAIFHULBGXAKX-VAWYXSNFBT | | InChIKey = OZAIFHULBGXAKX-VAWYXSNFBT | ||
| | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | |||
| | StdInChI = 1S/C8H12N4/c1-7(2,5-9)11-12-8(3,4)6-10/h1-4H3/b12-11+ | | StdInChI = 1S/C8H12N4/c1-7(2,5-9)11-12-8(3,4)6-10/h1-4H3/b12-11+ | ||
| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | |||
| | StdInChIKey = OZAIFHULBGXAKX-VAWYXSNFSA-N | | StdInChIKey = OZAIFHULBGXAKX-VAWYXSNFSA-N | ||
| | CASNo = 78-67-1 | | CASNo = 78-67-1 | ||
Revision as of 20:40, 26 May 2011
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| Names | |
|---|---|
| IUPAC name 2,2′-Azobis(2-methylpropionitrile) | |
| Other names
Azobisisobutyronitrile Azobisisobutylonitrile AIBN | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.001.030 
|
| PubChem CID | |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C8H12N4 |
| Molar mass | 164.21 g/mol |
| Appearance | white crystalline |
| Density | 1.1 |
| Melting point | 103–105 °C |
| Boiling point | °C |
| Solubility in water | ? |
| Structure | |
| Dipole moment | (gas) |
| Hazards | |
| Flash point | ? |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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Azobisisobutyronitrile is a 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 and Wako.
See also
- 1,1'-Azobis(cyclohexanecarbonitrile) or ABCN is another free radical initiator
References
External links
- SIDS Initial Assessment Report for 2,2’-Azobis(2-methylpropionitrile) from the Organisation for Economic Co-operation and Development (OECD)