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Sigma-Aldrich

Azobisisobutyronitrile

12 wt. % in acetone

Synonym(s):

2,2′-Azobis(2-methylpropionitrile) solution, radical initiator, α,α,′-Azoisobutyronitrile solution, AIBN solution

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About This Item

Empirical Formula (Hill Notation):
C8H12N4
CAS Number:
78-67-1
Molecular Weight:
164.21
MDL number:
MFCD00013808
UNSPSC Code:
12162002
PubChem Substance ID:
329767372

form

liquid

concentration

12 wt. % in acetone

refractive index

n20/D 1.368

density

0.808 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CC(C)(\N=N\C(C)(C)C#N)C#N

InChI

1S/C8H12N4/c1-7(2,5-9)11-12-8(3,4)6-10/h1-4H3/b12-11+

InChI key

OZAIFHULBGXAKX-VAWYXSNFSA-N

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General description

Azobisisobutyronitrile (AIBN) is an azo-compound and is widely used as a free radical initiator. This compound has labile carbon-nitrogen covalent bond which undergoes homolytic scission under thermal, chemical or photochemical conditions producing free radicals. They are useful in many reactions like halogenation, polymerisation of vinyl monomers, grafting reactions, curing of rubbers and unsaturated polymers and cross-linking of polyolefins.

Application

  • Used as an initiator in the synthesis of highly cross-linked Poly(divinylbenzene) (PDVB) polymers.
  • Used as an initiator in the polymerization process of 2-hydroxyethyl methacrylate (HEMA).

Features and Benefits

Decomposes unimolecularly at good rates without much variation from one solvent to another.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319,H336

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH044,EUH066

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

1.4 °F

Flash Point(C)

-17 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Biomaterials based on 2-hydroxyethyl methacrylate: the influence of the initiator type
Nita, L. E., Chiriac, A. P., Nistor, M. T., & Stoica, I.
Rev. Roum. Chim., 56(5), 537-543 (2011)
Synthesis of highly cross-linked polymers in supercritical carbon dioxide by heterogeneous polymerization.
Cooper, A. I., Hems, W. P., & Holmes, A. B.
Macromolecules, 32(7), 2156-2166 (1999)
Initiator efficiency in radical polymerization
Walling, C.
Journal of Polymer Science, 14(74), 214-217 (1954)
Selected radical azoinitiators in the synthesis of solvent-borne acrylic pressure-sensitive adhesives
Pabin-Szafko, B., Wisniewska, E., & Czech, Z.
Chemistry and Chemical Technology, 3(2), 101-106 (2009)
Lianghui Liu et al.
Organic letters, 14(22), 5692-5695 (2012-10-31)
In the presence of a catalytic amount of radical initiator AIBN, primary amines are oxidatively coupled to imines and tertiary amines are cyanated to α-aminonitriles. These "metal-free" aerobic oxidative coupling reactions may find applications in a wide range of "green"
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