2,2'-Azobis(2-methylpropionitrile)

Base Information

• Chemical Name: 2,2'-Azobis(2-methylpropionitrile)
• CAS No.: 78-67-1
• Deprecated CAS: 39322-24-2,58449-80-2,67035-64-7,76012-28-7,80748-81-8,95210-41-6,161755-85-7,161755-85-7,58449-80-2,67035-64-7,76012-28-7,80748-81-8,95210-41-6
• Molecular Formula: C8H12N4
• Molecular Weight: 164.21
• Hs Code.: 29269090
• European Community (EC) Number: 201-132-3,829-366-7
• ICSC Number: 1090
• NSC Number: 68042,1496
• UN Number: 3234,1325
• UNII: FZ6PX8U5YB
• DSSTox Substance ID: DTXSID1026457,DTXSID70859108
• Nikkaji Number: J1.955K
• Wikipedia: Azobisisobutyronitrile
• Wikidata: Q423679
• ChEMBL ID: CHEMBL1886625
• Mol file: 78-67-1.mol

Synonyms:Propanenitrile,2,2'-azobis[2-methyl- (9CI);Propionitrile, 2,2'-azobis[2-methyl- (8CI);2,2'-Azobis(2-cyanopropane);2,2'-Azobis[isobutyronitrile];2,2'-Azodiisobutyronitrile;2,2'-Dimethyl-2,2'-azodipropionitrile;ABN-R;AIBN;AZDH;AZDN;Aceto AZIB;Azobisisobutyronitrile;Azodiisobutyronitrile;ChKhE57;ChKhZ 57;Genitron AZDN;Genitron AZDN-FF;KB-P 13;KE-P 13;ME 800;N,N'-Azobis(isobutyronitrile);N,N'-Bis(2-cyano-2-propyl)diazene;NSC 1496;NSC68042;Perkadox AIBN;Peroxan AZDN;Pianofor An;Porofor ChKhZ 57;Porofor N;V60;V 60 (polymerization catalyst);Vazo 64;a,a'-Azobis(isobutyronitrile);a,a'-Azodiisobutyric acid dinitrile;a,a'-Azodiisobutyronitrile;2,2'-Azobisisobutyronitrile;

Chemical Property of 2,2'-Azobis(2-methylpropionitrile)

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0.81Pa at 24.85℃
• Melting Point: 102-104 °C (dec.)(lit.)
• Refractive Index: n20/D1.495
• Boiling Point: 236.2 °C at 760 mmHg
• Flash Point: 96.6 °C
• PSA: 72.30000
• Density: 0.95 g/cm³
• LogP: 2.04296
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 164.106196400
• Heavy Atom Count: 12
• Complexity: 251
• Transport DOT Label: Flammable Solid

Purity/Quality:

98%min ^*data from raw suppliers

2,2'-Azobis(isobutyronitrile) 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): E,Xn
• Hazard Codes: E,Xn,F,Xi
• Statements: 2-11-20/22-52/53-67-65-48/20-38-63-66-36
• Safety Statements: 39-41-47-61-62-36/37-16-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC(C)(C#N)N=NC(C)(C)C#N
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance may cause effects on the central nervous system.
• Effects of Long Term Exposure: The substance may have effects on the liver.
• Description: Azobisisobutyronitrile (abbreviated AIBN) is an organic compound with the formula [(CH3)2C(CN)]2N2. This white powder is soluble in alcohols and common organic solvents but is insoluble in water. It is often used as a foamer in plastics and rubber and as a radical initiator. It's soluble in a wide variety of organic solvents, including alcohol-based solvents. Insoluble in water and denser than water. Moderately toxic by ingestion. Readily ignited by sparks or flames. Burns intensely and persistently. Toxic oxides of nitrogen produced during combustion. Used as a catalyst, in vinyl polymerizations and a blowing agent for plastics.
• Uses: 2,2'-Azobis(2-methylpropionitrile) is used as an initiator in polymer radical polymerization because its molecules can easily undergo split reactions and form molecules with high activation energy. 2,2'-Azobis(2-methylpropionitrile) (AIBN) is the most commonly used azo initiator. Its characteristic is that the decomposition reaction is relatively stable, only one kind of free radical is generated, and basically no induced decomposition occurs, so it is often used in the kinetics research of free radical polymerization. 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. AIBN can be used as an initiator in the synthesis of highly cross-linked Poly(divinylbenzene) (PDVB) polymers. It also can be used as an initiator in the polymerization process of 2-hydroxyethyl methacrylate (HEMA). The polymerization initiator for Vinyl chloride, vinyl acetate, acrylonitrile and blowing agent for rubber, plastic , in an amount of 10% to 20%. This product can also be used as curing agents, pesticides and organic synthesis intermediates. This product is a highly toxic substance, mice are orally LD5017.2~25mg/kg, the organic cyanide released by the decomposition when it is heated has a greater poison on the human body . Used as an initiator in the synthesis of highly cross-linked Poly(divinylbenzene) (PDVB) polymers. 1 Used as an initiator in the polymerization process of 2-hydroxyethyl methacrylate (HEMA). 2 foaming agent and inhibitor in plastic and elastomer materials 2,2′-Azobis(2-methylpropionitrile) (AIBN) is a radical initiator. AIBN solution can be used to initiate radical-induced reactions, specifically free-radical polymerizations. It can be used in:Synthesis of styrene-vinyl pyridine diblock copolymers by reversible addition-fragmentation chain transfer (RAFT) polymerization.Preparation of silicon oxycarbide glasses.Synthesis of poly [N-(p-vinyl benzyl) phthalimide] for the preparation of titanium dioxide composites for electrophoretic displays.
• Production method: Acetone, hydrazine hydrate and sodium cyanide as raw materials: The temperature of condensation reaction above is 55~60 ℃, reaction time is 5h, and then cool down to 25~30 ℃ ,time is 2h. When to be cooled to below 10 ℃,begin to flow chlorine and carry out the reaction at below 20 ℃. Ratio of material: HCN: acetone: hydrazine = 1L:1.5036kg:0.415kg. Acetone cyanide alcohol and hydrazine hydrate react, and then the use of chlorine oxidation or amino nitrile with sodium hypochlorite oxidation.

Technology Process of 2,2'-Azobis(2-methylpropionitrile)

There total 10 articles about 2,2'-Azobis(2-methylpropionitrile) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

2,2'-hydrazobis(2-methylpropionitrile) (6869-07-4) → 2,2'-azobis(isobutyronitrile) (78-67-1)

Guidance literature:

With potassium hydroxide; potassium hexacyanoferrate(III); pyrographite; In dichloromethane; at 40 ℃; for 6h;

DOI:10.1246/bcsj.55.3541

Reference yield: 93.8%

cetyltrimethylammonium chloride (112-02-7,79728-63-5) + 2-amino-2-cyanopropane (19355-69-2) → 2,2'-azobis(isobutyronitrile) (78-67-1)

Guidance literature:

With sodium hypochlorite;

Reference yield: 72.0%

2,2'-dimethyl-2,2'-hydrazo-di-butyronitrile (171915-82-5) → 2,2'-azobis(isobutyronitrile) (78-67-1)

Guidance literature:

With oxygen; tetra-N-butylammonium tribromide; sodium nitrite; In 1,4-dioxane; water; at 60 ℃; for 4h; under 760.051 Torr; Sealed tube;

upstream raw materials:

2,2'-hydrazobis(2-methylpropionitrile)

bis-(1-chloro-1-methyl-ethyl)-diazene

sodium cyanide

2-amino-2-cyanopropane

Downstream raw materials:

(1,3,3,3-tetrachloro-propyl)-boronic acid dibutyl ester

meta-bromobenzyl bromide

1-bromomethyl-3-nitrobenzene

1-bromomethyl-4-nitro-benzene

Refernces

• 1、 -. "PROCESS FOR SYNTHESIZING AZO COMPOUNDS". Paragraph 0090-0093. . Retrieved 2021/01/26.
• 2、 -. "METHOD FOR PRODUCING AZO COMPOUNDS". Paragraph 0046. . Retrieved 2018/04/14.