Basic information
- Standard SMILES
CC(C)(C#N)N=NC(C)(C)C#N- InChIKey
OZAIFHULBGXAKX-UHFFFAOYSA-N- Molecular formula
- C8H12N4
- Average molar mass
- 164.21 g/mol
- Monoisotopic mass
- 164.10619638
Overview
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.
Names & identifiers
- Preferred name
- Azobisisobutyronitrile
- IUPAC
- 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile
- English name
- AIBN
- Molecular formula
- C8H12N4
- Molecular weight
- 164.21
Names & synonyms
78-67-12,2'-Azobis(2-methylpropionitrile)AzobisisobutyronitrileAzdhPorofor NAceto AZIBPianofor anPorofor 57Azobis(isobutyronitrile)Chkhz 57VAZO 64AZODIISOBUTYRONITRILE
Show more names
AIBNABINAZOISOBUTYRONITRILEAIVN2,2'-Azobisisobutyronitrile2,2-AZOBIS(2-METHYLPROPIONITRILE)ALPHA,ALPHA'-AZOISOBUTYRONITRILEPropanenitrile, 2,2'-azobis[2-methyl-
2,2'-Azobis(2-methylpropanenitrile)DTXSID10264572,2'-azobis(2-cyanopropane)PERKADOX AIBNDTXCID60809637alpha,alpha'-azobis(isobutyronitrile)Azobis[isobutyronitrile]2,2'-Azobis[2-methylpropionitrile]
Database identifiers
- CAS
34241-39-9、78-67-1- PubChem CID
- 6547
- DTXSID
DTXSID1026457- ChEMBL
CHEMBL1886625- ChEBI
CHEBI:189360- UNII
- FZ6PX8U5YB
- EC Number
- 201-132-3、829-366-7
- Nikkaji
- J1.955K、J3.670.816F
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 72.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 251
Experimental & physicochemical properties
Chemical Classes
Nitrogen Compounds -> Nitriles
Flammable agents - 3rd degree
SpringerMaterials PropertiesBoiling point
Density1.1 g/cm³
Color/Form
CRYSTALS FROM ETHANOL + WATER
WHITE POWDER
Solubility
SOL IN METHANOL @ 0, 20, 40 °C: 1.8, 4.96, 16.06 G/100 ML; SOL IN ETHANOL @ 0, 20, 40 °C: 0.58, 2.04, 7.15 G/100 ML
INSOL IN WATER; SOL IN MANY ORG SOLVENTS; SOL IN VINYL MONOMERS
Solubility in water at 20 °C: none
Melting Point221 °F (105 °C)
Vapor Pressure
0.0067 [mmHg]
Vapor pressure, Pa at 20 °C:
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description
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.
Dry Powder; Other Solid; Large Crystals; CBI
White solid; [ICSC] Fine white crystals; [MSDSonline]
WHITE POWDER.
Autoignition Temperature
147 °F (64 °C)
64 °C
Other Experimental PropertiesDECOMPOSES @ 107 °C
Physicochemical properties
- Melting point
- 102 · 102-104 °C (dec.)(lit.)
- Boiling point
- 281.68 °C · 281.68°C (rough estimate)
- Density
- 1.11 · 1.11
- vapor pressure
- 0.81 Pa · 0.81Pa at 24.85℃
- refractive index
- 20 · n20/D1.495
- Flash point
- 4 ℃ · 4℃
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- color
- Crystals from EtOH
- Odor
- odorless
- Water Solubility
- Insoluble
- Specific Heat Capacity
- 1.45 J/ · Cp(crystal): 1.45 J/(g·K), at 25℃
- Merck
- 13 · 13,920
- BRN
- 1708400 · 1708400
- Henry's Law Constant
- 2.4 · 2.4×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Stability
- Stability Flammable solid. Shock sensitive. Thermally unstable. May be explosive in combination with acetone or heptane. Incompatible with oxidizing agents.
- InChI
- 1S/C8H12N4/c1-7(2,5-9)11-12-8(3,4)6-10/h1-4H3/b12-11+
- InChIKey
- OZAIFHULBGXAKX-VAWYXSNFSA-N
- SMILES
- CC(C)(\N=N\C(C)(C)C#N)C#N
- LogP
- 1.1 at · 1.1 at 25℃
- CAS DataBase Reference
- 78 · 78-67-1(CAS DataBase Reference)
- Indirect Additives used in Food Contact Substances
- AZO-BIS-ISOBUTYRONITRILE
- FDA 21 CFR
- 175.105 · 175.105; 176.170; 177.2420
- FDA UNII
- 6 PX8U5YB · FZ6PX8U5YB
- NIST Chemistry Reference
- 2 · 2,2'-Azo-bis-isobutyronitrile(78-67-1)
- EPA Substance Registry System
- Azobis(isobutyronitrile) (78-67-1)
- UNSPSC Code
- 12352102 · 12352102
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS06,GHS08
- Signal word
- Danger
- Hazard statements
- 301 · H301+H331-H361-H373-H412-H242
- Precautionary statements
- 501 · P501-P273-P260-P270-P202-P220-P210-P234-P201-P271-P264-P280-P370+P378-P308+P313-P301+P310+P330-P304+P340+P311-P411-P420-P403+P233-P403+P235-P405
- target organs
- Central nervous system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- E,Xn,F,Xi
- Risk Statements
- 2 · 2-11-20/22-52/53-67-65-48/20-38-63-66-36
- Safety Statements
- 39 · 39-41-47-61-62-36/37-16-26
- RIDADR
- 3234 · UN 3234 4.1
- WGK Germany
- 2 · 2
- RTECS
- 800000 · UG0800000
- F
- 4.4 · 4.4
- TSCA
- TSCA listed
- HazardClass
- 4.1 · 4.1
- PackingGroup
- II
- HS Code
- 29269090 · 29269090
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 Asp · Aquatic Chronic 3Asp. Tox. 1Flam. Liq. 2Repr. 2Skin Irrit. 2STOT RE 2STOT SE 3
- Hazardous Substances Data
- 78 · 78-67-1(Hazardous Substances Data)
- Toxicity
- 670 mg/kg · LDLo orl-rat: 670 mg/kg 34ZIAG 0,117,69
- REACH Registrations
- Active
- Excepted Quantities
- Forbidden
Safety & regulation
GHS classification
GHS Classification
Danger
H242: Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]
P210, P234, P235, P240, P261, P264, P270, P271, P273, P280, P301+P317, P304+P340, P317, P330, P370+P378, P403, P410, P411, P420, and P501 (click each P-code to see the statement)
Danger
H242 (100%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]
P210, P234, P235, P240, P261, P264, P270, P271, P273, P280, P301+P317, P304+P340, P317, P330, P370+P378, P403, P410, P411, P420, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Chemical: Propanenitrile, 2,2'-azobis[2-methyl-
Propanenitrile, 2,2'-(1,2-diazenediyl)bis[2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanenitrile, 2,2'-(1,2-diazenediyl)bis[2-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 28-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14322
Propanenitrile, 2,2'-azobis(2-methyl)-: HSNO Approval: HSR001429 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Other Safety InformationIMAP assessments - Propanenitrile, 2,2'-azobis[2-methyl-: Human health tier I assessment
DOT LabelFlammable Solid
Fire Hazards
Excerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:
Highly flammable. Finely dispersed particles form explosive mixtures in air. Risk of fire and explosion when dissolving in organic solvents. Explosive.
Health HazardsExcerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:
Hazards Summary
Forms hydrogen cyanide in the body; [Merck Index] Decomposed by warming forming toxic fumes such as tetramethylsuccinonitrile and cyanide; May decompose explosively from heating, shock, friction, or concussion; May cause CNS and liver effects; [ICSC] May form explosive mixture of dust in air; May self-decompose or self-ignite from heat, chemical reaction, or impact; [CAMEO] Effects in high-dose animal studies include toxicity to liver and kidneys; [eChemPortal: SIDSUNEP] Highly flammable; May explode from shock, friction, fire, or other source of ignition; May cause irritation; Targets the CNS, liver, and kidneys; [MSDSonline] See NITRILES.
Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds
EC ClassificationSymbol: E, Xn; R: 2-11-20/22-52/53; S: (2)-39-41-47-61
UN ClassificationUN Hazard Class: 4.1
Reactivity AlertsExplosive
Reactivity Profile
Self-decomposition or self-ignition may be triggered by heat, chemical reaction, friction or impact. Self-accelerating decomposition may occur if the specific control temperature is not maintained. These materials are particularly sensitive to temperature rises. AZODIISOBUTYRONITRILE is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.
Chemical Dangers
Decomposes on warming. This produces toxic fumes of tetramethylsuccinonitrile (see ICSC 1121) and cyanide. May decompose explosively on shock, friction or concussion. May explode on heating. Reacts violently with alcohols, oxidants, ketones such as acetone, aldehydes and hydrocarbons such as heptane. This generates fire and explosion hazard.
Safety & protection
Fire Fighting
Excerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:
Use water in large amounts, water spray. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Give a slurry of activated charcoal in water to drink. Refer for medical attention .
First AidExcerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:
Safe StorageFireproof. Cool. Separated from strong oxidants and incompatible materials. See Chemical Dangers.
Nonfire Spill ResponseExcerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:
Spillage Disposal
Consult an expert! Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Remove all ignition sources. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.
Isolation and EvacuationExcerpt from ERG Guide 150 [Substances (Self-Reactive / Temperature Controlled)]:
Eye PreventionWear safety goggles or eye protection in combination with breathing protection.
Fire PreventionNO open flames, NO sparks and NO smoking. Do NOT expose to friction or shock. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. Prevent build-up of electrostatic charges (e.g., by grounding).
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
Skin PreventionProtective gloves.
Exposure PreventionPREVENT DISPERSION OF DUST!
Toxicology
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body by ingestion.
Signs and SymptomsHeadache. Nausea. Weakness. Convulsions.
ICSC Environmental DataThe substance is harmful to aquatic organisms. The substance may cause long-term effects in the aquatic environment.
Human Toxicity ExcerptsMAY BE TOXIC BY INGESTION.
Probable Routes of Human Exposure...IS TOXIC, & RELEASES NITROGEN GAS & RESIDUE OF TETRAMETHYL SUCCINIC DINITRILE, WHICH PERSISTS IN FOAM. THIS COMPD...HAS BEEN BELIEVED TO BE CAUSE OF HEADACHE, NAUSEA, & OTHER ILL-DEFINED SYSTEMIC COMPLAINTS IN WORKERS.
Toxicity DataLC (rat) > 12,000 mg/m3/4h
Safety data
- F
- 4.4
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- UG0800000
- ridadr
- UN 3234 4.1
- hs_code
- 29269090
- Toxicity
- LDLo orl-rat: 670 mg/kg 34ZIAG 0,117,69
- risk_code
- 2-11-20/22-52/53-67-65-48/20-38-63-66-36
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS08
- hazard_code
- E,Xn,F,Xi
- safety_code
- 39-41-47-61-62-36/37-16-26
- hazard_class
- 4.1
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- target organs
- Central nervous system
- Hazard statements
- H301+H331-H361-H373-H412-H242
- Excepted Quantities
- Forbidden
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 3Asp. Tox. 1Flam. Liq. 2Repr. 2Skin Irrit. 2STOT RE 2STOT SE 3
- Precautionary statements
- P501-P273-P260-P270-P202-P220-P210-P234-P201-P271-P264-P280-P370+P378-P308+P313-P301+P310+P330-P304+P340+P311-P411-P420-P403+P233-P403+P235-P405
- Hazardous Substances Data
- 78-67-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/MetabolitesIN ORGANISM, FORMS HCN WHICH IS FOUND IN BLOOD, LIVER & BRAIN.
Uses & manufacturing
Uses
Used as blowing agent (elastomers and plastics), catalyst (vinyl polymerizations), curing agent (unsaturated polyester resins), and fumigant (when heated); [HSDB]
Plastic Composites Manufacturing [Category: Industry]
BLOWING AGENT FOR ELASTOMERS & PLASTICS; INITIATOR FOR FREE RADICAL REACTIONS
CATALYST FOR VINYL POLYMERIZATIONS & FOR CURING UNSATURATED POLYESTER RESINS
AZOBISNITRILES ARE CARRIER GASES FOR FUMIGANTS. COMPOUND CONTAINING PERMETHRIN 10, 2,2'-AZOBISISOBUTYRONITRILE 80, & MOLDING AGENT 10 PARTS WAS GRANULATED. WHEN HEATED 92% OF PERMETHRIN GASIFIED.
U.S. Production2023: 1,000,000 - <2,500,000 lb
Consumer UsesOther
Industry UsesChain transfer agent
Methods of Manufacturing
...BY OXIDATION OF ALPHA,ALPHA'-HYDRAZOBUTYRIC ACID DINITRILE: OVERBERGER ET AL, J AM CHEM SOC 71, 2661 (1949); HORNER, SCHWENK, ANN 566, 69 (1950); FROM 2-AMINOISOBUTYRONITRILE + NAOCL: BRITISH PATENT 672,106 (1952 TO DU PONT)...
...FROM 2,2'-DICHLORO-2,2'-AZOPROPANE: BENZING, ANN 631, 1 (1960); BRITISH PATENT 929,182 (1963 TO MONSANTO).
General Manufacturing Information
Plastics Material and Resin Manufacturing
Propanenitrile, 2,2'-(1,2-diazenediyl)bis[2-methyl-: ACTIVE
Applications
DescriptionAzobisisobutyronitrile (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.
Uses2,2'-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.
UsesAzobisisobutyronitrile (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).
UsesThe 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 .
DescriptionAzobisisobutylonitrile (AIBN) is a white crystallinecompound. Molecular weight= 164.21; Specific gravity(H2O:1)= 1.11 at 25℃; Boiling point= decomposes;Freezing/Melting point= 99°103℃ (decomposes);Autoignition temperature= 63℃. NFPA 704 M HazardIdentification (based on NFPA-704M Rating System):Health 3, Flammability 2, Reactivity 2. Insoluble in water.
UsesUsed 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
Usesfoaming agent and inhibitor in plastic and elastomer materials
Uses2,2′-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.
General DescriptionInsoluble 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.
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Additional notes
DefinitionChEBI: (E)-Azobis(isobutyronitrile) is an azo compound.
Related reactions
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