2,2'-Azobisisobutyronitrile supplier

Name
2,2'-Azobis(2-methylpropionitrile)
EINECS 201-132-3
CAS No. 78-67-1
Article Data35
CAS DataBase
Density 0.95 g/cm³
Solubility Insoluble in water
Melting Point 102-104 °C (dec.)(lit.)
Formula C₈H₁₂N₄
Boiling Point 236.2 °C at 760 mmHg
Molecular Weight 164.21
Flash Point 96.6 °C
Transport Information UN 2952/3
Appearance white solid
Safety 39-41-47-61
Risk Codes 2-11-20/22-52/53
Molecular Structure
Hazard Symbols E,Xn
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;
PSA 72.30000
LogP 2.04296

Synthetic route

: 6869-07-4
2,2'-hydrazobis(2-methylpropionitrile)

: 78-67-1
2,2'-azobis(isobutyronitrile)

Conditions

Conditions	Yield
With potassium hydroxide; potassium hexacyanoferrate(III); pyrographite In dichloromethane at 40℃; for 6h;	99.5%
With hydrogenchloride; molybdophosphoric acid hydrate; dihydrogen peroxide; sodium docusate; sodium bromide In water at 16 - 17℃; for 4.5h; Reagent/catalyst;	95%
With dihydrogen peroxide In acetonitrile at 20℃; Temperature; Solvent;	95.6%

: 112-02-7
cetyltrimethylammonium chloride

: 19355-69-2
2-amino-2-cyanopropane

: 78-67-1
2,2'-azobis(isobutyronitrile)

Conditions

Conditions	Yield
With sodium hypochlorite	93.8%

: 171915-82-5
2,2'-dimethyl-2,2'-hydrazo-di-butyronitrile

: 78-67-1
2,2'-azobis(isobutyronitrile)

Conditions

Conditions	Yield
With oxygen; tetra-N-butylammonium tribromide; sodium nitrite In 1,4-dioxane; water at 60℃; under 760.051 Torr; for 4h; Sealed tube;	72%

: 29540-62-3
bis-(1-chloro-1-methyl-ethyl)-diazene

: 143-33-9
sodium cyanide

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 19355-69-2
2-amino-2-cyanopropane

: 78-67-1
2,2'-azobis(isobutyronitrile)

Conditions

Conditions	Yield
With sodium hypochlorite
With calcium hypochlorite
With oxygen; 1.5% Au/TiO2 In toluene at 100℃; under 2250.23 - 3750.38 Torr; for 40h;	46 %Chromat.

: 6869-07-4
2,2'-hydrazobis(2-methylpropionitrile)

: 71-43-2
benzene

: 94-36-0
dibenzoyl peroxide

: 78-67-1
2,2'-azobis(isobutyronitrile)

...Expand

: α,α'-(dinitroso-hydrazo)-di-isobutyronitrile

: 7732-18-5
water

: 78-67-1
2,2'-azobis(isobutyronitrile)

Conditions

Conditions	Yield
at 60℃;

hydrazoisobutyric acid dinitrile: hydrazoisobutyric acid dinitrile

: 78-67-1
2,2'-azobis(isobutyronitrile)

Conditions

Conditions	Yield
With hydrogenchloride; ethanol; bromine

: 6869-07-4
2,2'-hydrazobis(2-methylpropionitrile)

: 71-43-2
benzene

sodium peroxybenzoate: sodium peroxybenzoate

: 78-67-1
2,2'-azobis(isobutyronitrile)

...Expand

: 20334-43-4
dimethyl ditelluride

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 80-62-6
methacrylic acid methyl ester

poly(methyl methacrylate), -C(CN)(CH3)2 and -TeMe terminated, Mn 13100 by GPC, PDI 1.55 by GPC; monomer(s): methyl methacrylate; azoisobutyronitrile; dimethyl ditelluride: poly(methyl methacrylate), -C(CN)(CH3)2 and -TeMe terminated, Mn 13100 by GPC, PDI 1.55 by GPC; monomer(s): methyl methacrylate; azoisobutyronitrile; dimethyl ditelluride

Conditions

Conditions	Yield
at 80℃; for 0.5h;	100%

...Expand

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 141-32-2
acrylic acid n-butyl ester

poly(n-butyl acrylate), -C(CN)(CH3)2 and -deuterium terminated, Mn 4400 by GPC, PDI 1.19 by GPC and Mn 4300 by MALDI-TOF-MS, PDI 1.16 by MALDI-TOF-MS; monomer(s): n-butyl acrylate; azoisobutyronitrile: poly(n-butyl acrylate), -C(CN)(CH3)2 and -deuterium terminated, Mn 4400 by GPC, PDI 1.19 by GPC and Mn 4300 by MALDI-TOF-MS, PDI 1.16 by MALDI-TOF-MS; monomer(s): n-butyl acrylate; azoisobutyronitrile

Conditions

Conditions	Yield
Stage #1: 2,2'-azobis(isobutyronitrile); acrylic acid n-butyl ester With dimethyl ditelluride at 90℃; Stage #2: With 2,2'-azobis(isobutyronitrile); tributyltin deuteride In various solvent(s) at 80℃;	99%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 92-92-2
biphenyl-4-carboxylic acid

: N-(2-cyanopropan-2-yl)-N-isobutyrylbiphenyl-4-carboxamide

Conditions

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	99%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 88-67-5
2-Iodobenzoic acid

: N-(2-cyanopropan-2-yl)-2-iodo-N-isobutyrylbenzamide

Conditions

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	99%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: N,N-di-p-tolylmethacrylamide

: C22H24N2O

Conditions

Conditions	Yield
With copper(l) iodide In dichloromethane at 80℃; for 24h; Inert atmosphere;	99%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 1158958-94-1
N,N’-dimethyl-N,N’-di(4-pyridinyl)thiuram disulfide

: 1158958-96-3
2-cyanopropan-2-yl N-methyl-N-(pyridin-4-yl)carbamodithioate

Conditions

Conditions	Yield
In ethyl acetate for 16h; Reflux;	98.4%
In ethyl acetate for 16h; Reflux;	88%

: 110-86-1
pyridine

: 78-67-1
2,2'-azobis(isobutyronitrile)

: C18H22N6O12S4

Conditions

Conditions	Yield
With sulfur trioxide In dichloromethane for 24h;	98%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 99-94-5
p-Toluic acid

: N-(2-cyanopropan-2-yl)-N-isobutyryl-4-methylbenzamide

Conditions

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	98%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 98-73-7
4-(1,1-dimethylethyl)benzoic acid

: 4-tert-Butyl-N-(2-cyanopropan-2-yl)-N-isobutyrylbenzamideWhite

Conditions

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	98%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 52548-14-8
2-iodoyl-5-methylbenzoic acid

: N-(2-cyanopropan-2-yl)-2-iodo-N-isobutyryl-5-methylbenzamide

Conditions

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	98%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 5-methyl-N-(quinolin-8-yl)thiophene-2-carboxamide

: 3-cyano-5-methyl-N-(quinolin-8-yl)thiophene-2-carboxamide

Conditions

Conditions	Yield
With copper(II) nitrate hydrate; oxygen; silver(I) acetate In acetonitrile at 130℃; for 8h; Sealed tube; regioselective reaction;	98%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 444079-13-4
N-(2-naphthalenecarbonyl)-8-aminoquinoline

: 2-(quinolin-8-yl)-1H-benzo[f]isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With copper(II) nitrate hydrate; oxygen; silver(I) acetate In acetonitrile at 130℃; for 8h; Sealed tube; regioselective reaction;	98%

: 1277-43-6
cobaltocene

: 78-67-1
2,2'-azobis(isobutyronitrile)

: C5H5CoC5H5C(CH3)2CN

Conditions

Conditions	Yield
In toluene excess of Co(C5H5)2, complete exclusion of O2, in boiling toluene; mechanism discussed;;	97%
In toluene excess of Co(C5H5)2, complete exclusion of O2, in boiling toluene; mechanism discussed;;	97%
In further solvent(s) further solvent: styrol; excess of Co(C5H5)2, complete exclusion of O2;;	0%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 947-84-2
2-Biphenylcarboxylic acid

: N-(2-cyanopropan-2-yl)-N-isobutyrylbiphenyl-2-carboxamide

Conditions

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	97%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 88-65-3
2-bromobenzoic-acid

: 2-Bromo-N-(2-cyanopropan-2-yl)-N-isobutyrylbenzamide

Conditions

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	97%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 766-97-2
4-n-methylphenylacetylene

: 151589-34-3
3-(4-methylphenyl)-2-propynenitrile

Conditions

Conditions	Yield
With Cu-MOF In acetonitrile at 90℃; for 10h;	97%
With Cu(2+)C21H10NO6(3-)C12H10N2*H(1+) In acetonitrile at 90℃; for 8h;	93%
With copper(II) nitrate trihydrate; oxygen In acetonitrile at 80℃; for 12h;

: 766-98-3
1-ethynyl-4-fluorobenzene

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 575433-43-1
3-(4-fluorophenyl)-2-propynenitrile

Conditions

Conditions	Yield
With Cu-MOF In acetonitrile at 90℃; for 8h;	97%
With Cu(2+)C21H10NO6(3-)C12H10N2*H(1+) In acetonitrile at 90℃; for 8h;	94%
With copper(II) nitrate trihydrate; oxygen In acetonitrile at 80℃; for 12h;

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 2-(tert-butylamino)-1-(4-methylphenyl)-2-oxoethyl 3-phenyl-2H-azirine-2-carboxylate

: (Z)-2-(tert-butylamino)-1-(4-methylphenyl)-2-oxoethyl 3-amino-3-phenylacrylate

Conditions

Conditions	Yield
With tri-n-butyl-tin hydride In benzene at 90℃; for 0.5h;	97%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 32294-60-3
diphenyl ditelluride

: 80-62-6
methacrylic acid methyl ester

poly(methyl methacrylate), -C(CN)(CH3)2 and -TePh terminated, Mn 50100 by GPC, PDI 1.22 by GPC; monomer(s): methyl methacrylate; azoisobutyronitrile; diphenyl ditelluride: poly(methyl methacrylate), -C(CN)(CH3)2 and -TePh terminated, Mn 50100 by GPC, PDI 1.22 by GPC; monomer(s): methyl methacrylate; azoisobutyronitrile; diphenyl ditelluride

Conditions

Conditions	Yield
Stage #1: 2,2'-azobis(isobutyronitrile); diphenyl ditelluride In various solvent(s) at 80℃; for 3h; Stage #2: methacrylic acid methyl ester In various solvent(s) at 80℃; for 4h;	96%

...Expand

: bis(2,6-dimethylthiobenzoyl) disulfide

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 851729-41-4
2-cyanoprop-2-yl 2,6-dimethyldithiobenzoate

Conditions

Conditions	Yield
In ethyl acetate for 16h; Heating;	96%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 53151-59-0
C21H18O3

A: 1089675-68-2
3-hydroxy-2,2-dimethyl-4-oxo-3,4-diphenylbutyronitrile

B: 50654-42-7
3-hydroxy-2,2-dimethyl-3-phenylpropanenitrile

Conditions

Conditions	Yield
With titanium tetrachloride In benzene at 80℃; for 1.5h; Inert atmosphere;	A 96% B n/a
With titanium tetrachloride In benzene at 80℃; for 1.5h; Inert atmosphere;	A n/a B 71%

...Expand

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 65-85-0
benzoic acid

: N-(2-cyanopropan-2-yl)-N-isobutyrylbenzamide

Conditions

Conditions	Yield
In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;	96%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 5-phenyl-N-(quinolin-8-yl)furan-2-carboxamide

: 3-cyano-5-phenyl-N-(quinolin-8-yl)furan-2-carboxamide

Conditions

Conditions	Yield
With copper(II) nitrate hydrate; oxygen; silver(I) acetate In acetonitrile at 130℃; for 8h; Sealed tube; regioselective reaction;	96%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 33757-48-1
N-quinolin-8-yl-benzamide

: 19348-61-9
2-(quinolin-8-yl)-isoindoline-1,3-dione

Conditions

Conditions	Yield
With copper(II) nitrate hydrate; oxygen; silver(I) acetate In acetonitrile at 130℃; for 8h; Catalytic behavior; Temperature; Reagent/catalyst; Solvent; Time; Sealed tube; regioselective reaction;	96%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 33757-49-2
4-methyl-N-(quinolin-8-yl)benzamide

: 5-methyl-2-(quinolin-8-yl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With copper(II) nitrate hydrate; oxygen; silver(I) acetate In acetonitrile at 130℃; for 8h; Sealed tube; regioselective reaction;	96%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 536-74-3
phenylacetylene

: 935-02-4
2-cyano-1-phenylacetylene

Conditions

Conditions	Yield
With Cu-MOF In acetonitrile at 90℃; for 9h;	96%
With Cu(2+)C21H10NO6(3-)C12H10N2*H(1+) In acetonitrile at 90℃; for 8h;	94%
With copper(II) nitrate trihydrate; oxygen In acetonitrile at 80℃; for 12h;

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 3032-92-6
4-cyanophenylacetylene

: 4-(cyanoethynyl)benzonitrile

Conditions

Conditions	Yield
With Cu-MOF In acetonitrile at 90℃; for 9h;	96%
With Cu(2+)C21H10NO6(3-)C12H10N2*H(1+) In acetonitrile at 90℃; for 8h;	90%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 29079-00-3
4-ethynyl-1,1'-biphenyl

: 3-(1,1'-biphenyl)-4-yl-2-propynenitrile

Conditions

Conditions	Yield
With Cu-MOF In acetonitrile at 90℃; for 9h;	96%
With Cu(2+)C21H10NO6(3-)C12H10N2*H(1+) In acetonitrile at 90℃; for 8h;	88%

: 78-67-1
2,2'-azobis(isobutyronitrile)

: 137-26-8
Thiram

: dimethyl-dithiocarbamic acid cyano-dimethyl-methyl ester

Conditions

Conditions	Yield
In cyclohexane; chlorobenzene for 4h; Heating;	95%
In benzene for 24h; Heating;	93%

2,2'-Azobisisobutyronitrile Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

2,2'-Azobisisobutyronitrile Standards and Recommendations

DOT Classification: 4.1; Label: Flammable Solid, Explosive

2,2'-Azobisisobutyronitrile Specification

2,2'-Azobisisobutyronitrile, its cas register number is 78-67-1. It also can be called 2,2'-Dicyano-2,2'-azopropane; 2,2'-Dimethyl-2,2'-azodipropionitrile; AIBN; alpha,alpha'-Azodiisobutyronitrile; Azodiisobutyrodinitrile; Azobisisobutyronitrile. It is a white acicular crystal, which is insolvable in water, solvable in organic solvent such as methyl alcohol, ethanol, acetone, ethyl ether and light petroleum etc.lce point of pure product is 105^oC.

Physical properties about 2,2'-Azobisisobutyronitril are:
(1)ACD/LogP: 1.659; (2)ACD/LogD (pH 5.5): 1.66; (3)ACD/LogD (pH 7.4): 1.66; (4)ACD/BCF (pH 5.5): 10.74; (5)ACD/BCF (pH 7.4): 10.74; (6)ACD/KOC (pH 5.5): 190.35; (7)ACD/KOC (pH 7.4): 190.35; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.49; (11)Molar Refractivity: 49.674 cm³; (12)Molar Volume: 171.526 cm³; (13)Polarizability: 19.692 10-24cm³; (14)Surface Tension: 34.8530006408691 dyne/cm; (15)Density: 0.957 g/cm³; (16)Flash Point: 96.634 °C; (17)Enthalpy of Vaporization: 47.296 kJ/mol; (18)Boiling Point: 236.173 °C at 760 mmHg; (19)Vapour Pressure: 0.0480000004172325 mmHg at 25°C

Uses of 2,2'-Azobisisobutyronitril:
2,2'-Azobisisobutyronitrile is maily used as polymerization initiator of monomer such as chloroethylene,vinyl acetate,acrylonitrile,etc;also used as blowing agent for PVC,polyalkene,polyurethane,polyvinyl alcohol,acrylonitrile/butadiene copolymer,chloroethylene copolymer,acrylonitrile/ butadiene/styrene copolymer,polyisocyanate,polyvinyl acetate,polyamide and polyester,etc.Moreover,it is also used in other organic synthesis.

When you are using 2,2'-Azobisisobutyronitril, please be cautious about it as the following:
1. Wear eye/face protection;
2. In case of fire and/or explosion do not breathe fumes;
3. Keep at temperature not exceeding ... E C (to be specified by the manufacturer);
4. Avoid release to the environment. Refer to special instructions safety data sheet;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C8H12N4/c1-7(2,5-9)11-12-8(3,4)6-10/h1-4H3/b12-11+;
(2)InChIKey InChIKey=OZAIFHULBGXAKX-VAWYXSNFSA-N;
(3)SmilesC(\N=N\C(C#N)(C)C)(C#N)(C)C;

The toxicity data of 2,2'-Azobisisobutyronitrile is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LDLo	subcutaneous	50mg/kg (50mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Archiv fuer Toxikologie. Vol. 16, Pg. 367, 1957.
mouse	LD50	intraperitoneal	25mg/kg (25mg/kg)		National Technical Information Service. Vol. AD691-490,
mouse	LD50	oral	700mg/kg (700mg/kg)		"Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 146, 1989.
mouse	LDLo	subcutaneous	40mg/kg (40mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Archiv fuer Toxikologie. Vol. 16, Pg. 367, 1957.
rabbit	LDLo	subcutaneous	50mg/kg (50mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Archiv fuer Toxikologie. Vol. 16, Pg. 367, 1957.
rat	LC	inhalation	> 12gm/m3/4H (12000mg/m3)	BEHAVIORAL: EXCITEMENT SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE	National Technical Information Service. Vol. OTS0555369,
rat	LD50	intraperitoneal	25mg/kg (25mg/kg)	BEHAVIORAL: ATAXIA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: GENERAL ANESTHETIC	National Technical Information Service. Vol. OTS0555369,
rat	LD50	oral	100mg/kg (100mg/kg)	BEHAVIORAL: ATAXIA BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	National Technical Information Service. Vol. OTS0555369,
rat	LDLo	subcutaneous	30mg/kg (30mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Archiv fuer Toxikologie. Vol. 16, Pg. 367, 1957.

Product Name

2,2'-Azobis(2-methylpropionitrile)

Synthetic route

2,2'-Azobisisobutyronitrile Consensus Reports

2,2'-Azobisisobutyronitrile Standards and Recommendations

2,2'-Azobisisobutyronitrile Specification

Related Products

Hot Products