2,2'-Azobis(2,4-dimethyl)valeronitrile supplier

Name
2,2'-Azobis(2,4-dimethyl)valeronitrile
EINECS 224-583-8
CAS No. 4419-11-8
Article Data15
CAS DataBase
Density 0.93 g/cm³
Solubility 9.37mg/L at 20℃
Melting Point 45-70 °C
Formula C₁₄H₂₀N₄
Boiling Point 330.6 °C at 760 mmHg
Molecular Weight 248.371
Flash Point 153.8 °C
Transport Information UN 2953
Appearance odorless white solid
Safety 16-22-24/25-36/37/39-45
Risk Codes 2017/11/22
Molecular Structure
Hazard Symbols
Synonyms Pentanenitrile,2,2'-azobis[2,4-dimethyl- (9CI);Valeronitrile, 2,2'-azobis[2,4-dimethyl-(6CI,7CI,8CI);2,2'-Azobis[2,4-dimethylpentanenitrile];2,2'-Azodi(2,4-dimethylvaleronitrile);ADVN;AMVN;V 65;V 65 (polymerization catalyst);V 65B;Vazo 52;a,a'-Azobis(dimethylvaleronitrile);a,a'-Azobis(a,g-dimethylvaleronitrile);a,a'-Azobis[2,4-dimethylvaleronitrile];
PSA 72.30000
LogP 4.09536

Synthetic route

: 35017-47-1
2,4,2',4'-tetramethyl-2,2'-hydrazo-di-valeronitrile

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

Conditions

Conditions	Yield
With potassium hydroxide; potassium hexacyanoferrate(III); pyrographite In benzene at 30℃; for 6h;	100%
With oxygen; tetra-N-butylammonium tribromide; sodium nitrite In 1,4-dioxane; water at 40℃; under 760.051 Torr; for 4h; Sealed tube;	65%
With ammonium cerium (IV) nitrate; oxygen; acetic acid In 1,4-dioxane; water at 40℃; under 760.051 Torr; for 4h; Sealed tube;	56 %Chromat.

higher-melting N.N'-bis-<1.3-dimethyl-1-cyano-butyl>-hydrazine: higher-melting N.N'-bis-<1.3-dimethyl-1-cyano-butyl>-hydrazine

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

Conditions

Conditions	Yield
With hydrogenchloride; bromine higher-melting form of 1,3,1',3'-tetramethyl-1,1'-dicyano-azobutane;
With hydrogenchloride; chlorine higher-melting form of 1,3,1',3'-tetramethyl-1,1'-dicyano-azobutane;

lower-melting N.N'-bis-<1.3-dimethyl-1-cyano-butyl>-hydrazine: lower-melting N.N'-bis-<1.3-dimethyl-1-cyano-butyl>-hydrazine

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

Conditions

Conditions	Yield
lower-melting form of 1,3,1',3'-tetramethyl-1,1'-dicyano-azobutane;

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 106-45-6
para-thiocresol

: 2,4-dimethyl-2-(p-tolylthio)pentanenitrile

Conditions

Conditions	Yield
With 1,10-Phenanthroline; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 12h; Schlenk technique;	97%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 5873-93-8
bis(thiobenzoyl) disulfide

: 851729-55-0
2-cyano-4-methylpent-2-yl dithiobenzoate

Conditions

Conditions	Yield
In ethyl acetate Heating;	95%

: 3481-09-2
N-chlorophthalimide

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: C22H28ClN3O2

Conditions

Conditions	Yield
In o-xylene at 90℃; for 20h; Inert atmosphere; Schlenk technique;	95%

: 128-09-6
N-chloro-succinimide

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: C18H28ClN3O2

Conditions

Conditions	Yield
In o-xylene at 90℃; for 10h; Inert atmosphere; Schlenk technique;	94%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: C7H8ClNO2

: C21H32ClN3O2

Conditions

Conditions	Yield
In o-xylene at 90℃; for 10h; Inert atmosphere; Schlenk technique;	83%

: triphenylmethyl dithioisonicotinate

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 2-cyano-4-methylpentan-2-yl dithioisonicotinate

Conditions

Conditions	Yield
In ethyl acetate for 16h; Reflux;	78%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 82621-82-7
1-chloropiperidine-2,6-dione

: C19H30ClN3O2

Conditions

Conditions	Yield
In o-xylene at 90℃; for 10h; Inert atmosphere; Schlenk technique;	75%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: C8H10ClNO2

: C22H34ClN3O2

Conditions

Conditions	Yield
In o-xylene at 90℃; for 10h; Inert atmosphere; Schlenk technique;	71%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 2-(2’-hydroxyphenyl)imidazo[1,2-a]pyridine

: 2-((2-(2-hydroxyphenyl)imidazo[1,2-a]pyridin-3-yl)thio)-2,4-dimethylpentanenitrile

Conditions

Conditions	Yield
With sulfur; iodine In acetonitrile at 100℃; for 12h;	63%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 1182669-71-1
N-(2-methylbenzoyl)-8-aminoquinoline

: C24H25N3O

Conditions

Conditions	Yield
With nickel(II) sulphate; dipotassium peroxodisulfate; copper diacetate; Trimethylacetic acid In dimethyl sulfoxide; acetonitrile at 150℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	55%

: 851729-37-8
bis(3,5-bis(trifluoromethyl)thiobenzoyl) disulfide

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 851729-57-2
2-cyano-4-methylpent-2-yl 3,5-bis(trifluoromethyl)dithiobenzoate

Conditions

Conditions	Yield
In ethyl acetate Heating;	52%

: 851729-35-6
bis(4-cyanothiobenzoyl) disulfide

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 851729-56-1
2-cyano-4-methylpent-2-yl 4-cyanodithiobenzoate

Conditions

Conditions	Yield
In ethyl acetate Heating;	48%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 33757-54-9
4-chloro-N-(quinolin-8-yl)benzamide

: C23H22ClN3O

Conditions

Conditions	Yield
With nickel(II) sulphate; dipotassium peroxodisulfate; copper diacetate; Trimethylacetic acid In dimethyl sulfoxide; acetonitrile at 150℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	48%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 2446-83-5
di-isopropyl azodicarboxylate

: 768-60-5
4-methoxyphenylacetylen

: diisopropyl 1-[(E)-3-cyano-1-(4-methoxyphenyl)-3,5-dimethylhex-1-en-1-yl]-1,2-hydrazinedicarboxylate

Conditions

Conditions	Yield
With copper(I) bromide In acetonitrile at 80℃; for 8h; Schlenk technique; Inert atmosphere; stereoselective reaction;	47%

...Expand

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 4105-21-9
2-phenylimidazo[1,2-a]pyridine

: 2,4-dimethyl-2-((2-phenylimidazo[1,2-a]pyridin-3-yl)thio)pentanenitrile

Conditions

Conditions	Yield
With sulfur; iodine In acetonitrile at 100℃; for 12h;	40%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 1602924-87-7
C25H24CuN7(1+)*ClO4(1-)

: 292638-85-8
acrylic acid methyl ester

: C36H42N8O2

: C36H42N8O2

Conditions

Conditions	Yield
In acetonitrile at 90℃; for 12h; Schlenk technique; Inert atmosphere; Overall yield = 77 percent;	A 39% B 38%

...Expand

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

A: 85688-85-3
meso-2,3-Diisobutyl-2,3-dimethylbernsteinsaeuredinitril

: 80822-82-8, 85688-85-3
DL-2,3-Diisobutyl-2,3-dimethylbernsteinsaeuredinitril

Conditions

Conditions	Yield
In tetrachloromethane for 24h; Heating;	A 36% B 33%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 20710-49-0
bis(4-methoxyphenyl thiocarbonyl)disulfide

: 851729-58-3
2-cyano-4-methylpent-2-yl 4-methoxydithiobenzoate

Conditions

Conditions	Yield
In ethyl acetate Heating;	22.8%

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 6773-29-1
dimethyl diazomalonate

: 1211417-77-4
(1,3-dimethylimidazol-2-ylidene)borane

: (1-(2-cyano-4-methylpentan-2-yl)-2-(1,3-dimethoxy-1,3-dioxopropan-2-ylidene)hydrazinyl)(1,3-dimethyl-1H-imidazol-3-ium-2-yl)dihydroborate

Conditions

Conditions	Yield
With (1-(2-cyanopropan-2-yl)-2-(1,3-dimethoxy-1,3-dioxopropan-2-ylidene)hydrazinyl)(1,3-dimethyl-1H-imidazol-3-ium-2-yl)dihydroborate at 120℃; for 2h; Inert atmosphere;	18%

...Expand

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 59-02-9
Tocopherol

A: 1133295-25-6
8a-hydroperoxy α-tocopherone

B: 186429-17-4
4a,5-epoxy-8a-hydroperoxy-α-tocopherone

C: 121250-09-7
<8a(S),2'(S)>-8a-<(2,4-dimethyl-1-nitrilopent-2-yl)dioxy>tocopherone

D: 121186-95-6
<8a(S),2'(R)>-8a-<(2,4-dimethyl-1-nitrilopent-2-yl)dioxy>tocopherone

E: 121250-11-1
<8a(R),2'(S)>-8a-<(2,4-dimethyl-1-nitrilopent-2-yl)dioxy>tocopherone

F: 121250-10-0
<8a(R),2'(R)>-8a-<(2,4-dimethyl-1-nitrilopent-2-yl)dioxy>tocopherone

Conditions

Conditions	Yield
With oxygen In acetonitrile at 50℃; for 1h; Product distribution; Mechanism; var. time, in the presence of H2O;	A 3% B n/a C n/a D n/a E n/a F n/a

...Expand

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 45860-18-2
1,3,5-tribromo-2-nitroso-benzene

: 142599-92-6
C13H14Br3N2O

Conditions

Conditions	Yield
In benzene 1.) 60 deg C, 3 min, 2.) to 25 deg C, 2 min;

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 59-02-9
Tocopherol

A: 121250-09-7
<8a(S),2'(S)>-8a-<(2,4-dimethyl-1-nitrilopent-2-yl)dioxy>tocopherone

B: 121186-95-6
<8a(S),2'(R)>-8a-<(2,4-dimethyl-1-nitrilopent-2-yl)dioxy>tocopherone

C: 121250-11-1
<8a(R),2'(S)>-8a-<(2,4-dimethyl-1-nitrilopent-2-yl)dioxy>tocopherone

D: 121250-10-0
<8a(R),2'(R)>-8a-<(2,4-dimethyl-1-nitrilopent-2-yl)dioxy>tocopherone

Conditions

Conditions	Yield
With oxygen In acetonitrile at 50℃; for 1h; Further byproducts given;

...Expand

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: C14H25N4

Conditions

Conditions	Yield
With hydroquinone In methanol at 20℃; Mechanism; Irradiation; var. solvents, var. sensitizers; also with 2,2-azobis(propane-2-carboxamidine) dihydrochloride;
With hydroquinone In methanol at 20℃; Irradiation;

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 2-cyano-4-methylpentan-2-yl radical

Conditions

Conditions	Yield
With potassium phosphate; potassium chloride In acetonitrile at 22℃; Rate constant;

: 4419-11-8
2,2'-azobis-(2,4-dimethylvaleronitrile)

: 1244-78-6
2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone

A: 2150-41-6
methyl 2, 4-dimethoxybenzoate

B: 51116-92-8
methyl 4,6-dimethoxysalicylate

C: 25982-03-0
methyl 4,6-dimethoxy-2-(3,4-dimethoxybenzoyloxy)-salicylate

Conditions

Conditions	Yield
In benzene at 37℃; Product distribution; Decomposition; radical-capturing;

...Expand

2,2'-Azobis(2,4-dimethyl)valeronitrile Chemical Properties

IUPAC Name: 2-(2-Cyano-4-methylpentan-2-yl)diazenyl-2,4-dimethylpentanenitrile
Synonyms of 2,2'-Azobis(2,4-dimethyl)valeronitrile (CAS NO.4419-11-8): Pentanenitrile, 2,2'-(1,2-diazenediyl)bis(2,4-dimethyl-) ; Pentanenitrile, 2,2'-azobis(2,4-dimethyl-) ; 2,2'-Azobis(2,4-dimethylvaleronitrile)
CAS NO: 4419-11-8
Molecular Formula: C₁₄H₂₀N₄
Molecular Weight: 244.34
Molecular Structure:
EINECS: 218-254-8
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 6
Polar Surface Area: 72.3 Å²
Index of Refraction: 1.489
Molar Refractivity: 76.95 cm³
Molar Volume: 266.5 cm³
Surface Tension: 31.8 dyne/cm
Density: 0.93 g/cm³
Flash Point: 153.8 °C
Enthalpy of Vaporization: 57.32 kJ/mol
Boiling Point: 330.6 °C at 760 mmHg
Vapour Pressure: 0.000164 mmHg at 25°C
Melting point: 45-70 °C
Water solubility: Insoluble in water.
Product Categories of 2,2'-Azobis(2,4-dimethyl)valeronitrile (CAS NO.4419-11-8): Organics;pharmacetical
SMILES: CC(C)CC(C)(/N=N/C(C)(CC(C)C)C#N)C#N
InChI: InChI=1/C14H24N4/c1-11(2)7-13(5,9-15)17-18-14(6,10-16)8-12(3)4/h11-12H,7-8H2,1-6H3
InChIKey: WYGWHHGCAGTUCH-UHFFFAOYAF
Std. InChI: InChI=1S/C14H24N4/c1-11(2)7-13(5,9-15)17-18-14(6,10-16)8-12(3)4/h11-12H,7-8H2,1-6H3
Std. InChIKey: WYGWHHGCAGTUCH-UHFFFAOYSA-N

2,2'-Azobis(2,4-dimethyl)valeronitrile Safety Profile

RIDADR: UN 2953
HazardClass: 4.1
PackingGroup: II

2,2'-Azobis(2,4-dimethyl)valeronitrile Specification

2,2'-Azobis(2,4-dimethyl)valeronitrile (CAS NO.4419-11-8) is self-decomposition or self-ignition, this may be triggered by heat, chemical reaction, friction or impact. Self-accelerating decomposition may occur if the specific control temperature is not maintained. 2,2'-Azobis(2,4-dimethyl)valeronitrile 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.

Product Name

2,2'-Azobis(2,4-dimethyl)valeronitrile

Synthetic route

2,2'-Azobis(2,4-dimethyl)valeronitrile Chemical Properties

2,2'-Azobis(2,4-dimethyl)valeronitrile Safety Profile

2,2'-Azobis(2,4-dimethyl)valeronitrile Specification

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