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Merck
CN

768375

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
UNSPSC Code:
12162002
PubChem Substance ID:
329767372
MDL number:
MFCD00013808

Key Documents

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Product Name

Azobisisobutyronitrile, 12 wt. % in acetone

InChI

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

SMILES string

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

InChI key

OZAIFHULBGXAKX-VAWYXSNFSA-N

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

Quality Level

100

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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.

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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

EUH044,EUH066

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

1.4 °F

flash_point_c

-17 °C

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ1890
MKCX8132
MKCV7360
MKCW6068
MKCV2187

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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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