13472-08-7

Basic information

• Product Name: 2,2'-Azodi(2-methylbutyronitrile)
• Synonyms: vazo67;VAZO(R) 67;VAZO(R) CATALYST 67 FREE RADICAL SOURCE;2.2"-A20Bis (2-Methylbutyronitrile);2,2'-Azobis-(2-Methylbutyronitrile)(V59);2,2'-AZO-BIS-ISOAMYLONITRILE;Azobisisoamylonitrile;Butanenitrile, 2,2-azobis2-methyl-
• CAS NO: 13472-08-7
• Molecular Formula: C₁₀H₁₆N₄
• Molecular Weight: 192.26
• EINECS: 236-740-8
• Product Categories: Industrial/Fine Chemicals;Organics;pharmacetical
• Mol File: 13472-08-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 49-52 °C
• Boiling Point: 318.25°C (rough estimate)
• Flash Point: 118.9 °C
• Appearance: solid
• Density: 1.1
• Vapor Pressure: 0.354Pa at 25℃
• Refractive Index: 1.4910 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility: 392mg/L at 20℃
• Stability: Explosive. Risk of explosion if struck, ground or heated. Highly flammable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 2,2'-Azodi(2-methylbutyronitrile)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Azodi(2-methylbutyronitrile)(13472-08-7)
• EPA Substance Registry System: 2,2'-Azodi(2-methylbutyronitrile)(13472-08-7)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-22-2017/11/22
• Safety Statements: 47-36/37/39-24/25-16
• RIDADR: UN 3236 4.1
• WGK Germany: 1
• RTECS: EK4818750
• F: 4.4
• HazardClass: 4.1
• PackingGroup: II
• Hazardous Substances Data: 13472-08-7(Hazardous Substances Data)

Usage

Chemical Properties

solid

Hazard

Moderately toxic by ingestion.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits toxic vapors ofNOx.

Synthetic route

2,2'-dimethyl-2,2'-hydrazo-di-butyronitrile (171915-82-5) → azobis(2-cyanobutane) (13472-08-7)

Conditions	Yield
With trichloroisocyanuric acid In acetonitrile at 20℃;	95%
With oxone; potassium bromide In water at 20℃;	64%
With ammonium cerium (IV) nitrate; oxygen; acetic acid In 1,4-dioxane; water at 50℃; under 760.051 Torr; for 4h; Sealed tube;	64 %Chromat.
With chlorine; sodium bromide In water at 5℃; for 2h; Large scale;	134 kg

2-amino-2-methylbutanenitrile (4475-95-0) → azobis(2-cyanobutane) (13472-08-7)

Conditions	Yield
With calcium hypochlorite

α-(N-Dichloramino)-s-valeronitril (16248-72-9) → azobis(2-cyanobutane) (13472-08-7)

Conditions	Yield
With sodium hydroxide In methanol

α.α'-hydrazo--dinitrile → azobis(2-cyanobutane) (13472-08-7)

Conditions	Yield
With bromine

azobis(2-cyanobutane) (13472-08-7) + benzoic acid (65-85-0) → N-(2-cyanobutan-2-yl)-N-(2-methylbutanoyl)benzamide

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

azobis(2-cyanobutane) (13472-08-7) + 1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-ol (116460-49-2, 102990-13-6) → N-(2-cyanobutan-2-yl)-2-ethyl-5-(4-methoxyphenyl)-2-methyl-3-phenylpent-4-ynamide

Conditions	Yield
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; 4-nitrophenylboronic acid In Dimethyl ether at 100℃; for 12h; Glovebox;	95%

azobis(2-cyanobutane) (13472-08-7) + 1-chloropiperidine-2,6-dione (82621-82-7) → C15H22ClN3O2

Conditions	Yield
In o-xylene at 90℃; for 10h; Inert atmosphere; Schlenk technique;	95%

azobis(2-cyanobutane) (13472-08-7) + 5-hexynonitrile (14918-21-9) → hept-2-ynedinitrile (1174272-05-9)

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	92%

azobis(2-cyanobutane) (13472-08-7) + C8H10ClNO2 → C18H26ClN3O2

Conditions	Yield
In o-xylene at 90℃; for 10h; Inert atmosphere; Schlenk technique;	92%

N-chloro-succinimide (128-09-6) + azobis(2-cyanobutane) (13472-08-7) → C14H20ClN3O2

Conditions	Yield
In o-xylene at 90℃; for 10h; Inert atmosphere; Schlenk technique;	91%

azobis(2-cyanobutane) (13472-08-7) + 4-cyanophenylacetylene (3032-92-6) → 4-(cyanoethynyl)benzonitrile

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	88%

azobis(2-cyanobutane) (13472-08-7) + triphenylmethyl diethoxyphosphoryldithioformate (178878-92-7) → 2-cyanobut-2-yl diethoxyphosphoryldithioformate

Conditions	Yield
In ethyl acetate for 15h; Heating;	87%

N-propargylphthalimide (7223-50-9) + azobis(2-cyanobutane) (13472-08-7) → 4-(1,3-dioxoisoindolin-2-yl)but-2-ynenitrile

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	86%

N-chlorophthalimide (3481-09-2) + azobis(2-cyanobutane) (13472-08-7) → C18H20ClN3O2

Conditions	Yield
In o-xylene at 90℃; for 6h; Inert atmosphere; Schlenk technique;	86%

azobis(2-cyanobutane) (13472-08-7) + bis(thiobenzoyl) disulfide (5873-93-8) → 1-cyano-1-methylpropyl dithiobenzoate (220182-83-2)

Conditions	Yield
In ethyl acetate at 70℃; for 24h;	82%

azobis(2-cyanobutane) (13472-08-7) + N-(2-methylallyl)-N-phenylmethacrylamide (1600519-40-1) → 6-ethyl-3a,6,7a-trimethyl-2-phenylhexahydro-1H-isoindole-1,5(4H)-dione

Conditions	Yield
With air In water at 85℃; for 12h; Schlenk technique;	82%
In water at 85℃; for 12h; Schlenk technique; Sealed tube; Green chemistry;	82%

azobis(2-cyanobutane) (13472-08-7) + C14H17NO2 → 6-ethyl-2-(4-methoxyphenyl)-6,7a-dimethylhexahydro-1H-isoindole-1,5(4H)-dione

Conditions	Yield
With air In water at 85℃; for 12h; Schlenk technique;	81%
In water at 85℃; for 12h; Schlenk technique; Sealed tube; Green chemistry;	81%

azobis(2-cyanobutane) (13472-08-7) + 4-trifluoromethylphenylacetylene (705-31-7) → 3-[4-(trifluoromethyl)phenyl]-2-propynenitrile (1201634-58-3)

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	78%

azobis(2-cyanobutane) (13472-08-7) + 1-phenoxy-2-propyne (13610-02-1) → 4-phenoxybut-2-ynenitrile (110409-54-6)

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	78%

1-ethynyl-4-fluorobenzene (766-98-3) + azobis(2-cyanobutane) (13472-08-7) → 3-(4-fluorophenyl)-2-propynenitrile (575433-43-1)

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	77%

4-n-chlorophenylacetylene (873-73-4) + azobis(2-cyanobutane) (13472-08-7) → 3-(4-chlorophenyl)-2-propynenitrile (49748-63-2)

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	75%

1-styrenyloxytrimethylsilane (13735-81-4) + azobis(2-cyanobutane) (13472-08-7) → 2-ethyl-2-methyl-4-oxo-4-phenylbutanenitrile

Conditions	Yield
With copper(II) ethyl acetoacetate; silver carbonate In tetrahydrofuran at 100℃; for 12h; Glovebox; Schlenk technique; Inert atmosphere;	74%

4-bromo-1-ethynylbenzene (766-96-1) + azobis(2-cyanobutane) (13472-08-7) → 3-(4-bromophenyl)-2-propynenitrile

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Reagent/catalyst; Solvent; Schlenk technique;	73%

4-Phenyl-1-butyne (16520-62-0) + azobis(2-cyanobutane) (13472-08-7) → 5-phenylpent-2-ynenitrile (861370-36-7)

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	72%

azobis(2-cyanobutane) (13472-08-7) + di-isopropyl azodicarboxylate (2446-83-5) + 4-methoxyphenylacetylen (768-60-5) → diisopropyl 1-[(E)-3-cyano-1-(4-methoxyphenyl)-3-methylpent-1-en-1-yl]-1,2-hydrazinedicarboxylate

Conditions	Yield
With copper(I) bromide In acetonitrile at 80℃; for 8h; Schlenk technique; Inert atmosphere; stereoselective reaction;	72%

azobis(2-cyanobutane) (13472-08-7) + N-allyl-N-phenyl-2-methacrylamide (145784-90-3) → 6-ethyl-6,7a-dimethyl-2-phenylhexahydro-1H-isoindole-1,5(4H)-dione

Conditions	Yield
With air In water at 85℃; for 12h; Schlenk technique;	72%
In water at 85℃; for 12h; Schlenk technique; Sealed tube; Green chemistry;	72%

azobis(2-cyanobutane) (13472-08-7) + N-methyl-N-(2-(phenylethynyl)phenyl)-methacrylamide (1633007-86-9) → 8-ethyl-5,6a,8-trimethyl-10-phenyl-7,8-dihydrophenanthridine-6,9(5H,6aH)-dione

Conditions	Yield
With tetrabutylammonium acetate; copper(ll) bromide In water; acetonitrile at 65 - 85℃; for 24h; Schlenk technique; Inert atmosphere;	71%

azobis(2-cyanobutane) (13472-08-7) + 3-Phenyl-2-propyn-1-ol (1504-58-1) → N-(2-cyanobutan-2-yl)-2-ethyl-2-methyl-3-phenylpenta-3,4-dienamide

Conditions	Yield
With silver trifluoromethanesulfonate In dichloromethane at 100℃; for 12h; Glovebox;	71%

azobis(2-cyanobutane) (13472-08-7) + propargyl benzoate (6750-04-5) → 3-vyanoprop-2-ynyl benzoate

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	70%

azobis(2-cyanobutane) (13472-08-7) + 2-methyl-benzyl alcohol (89-95-2) → C13H16N2

Conditions	Yield
With Ni/C3N4 In acetonitrile at 140℃; for 16h; Autoclave; Inert atmosphere;	70%

azobis(2-cyanobutane) (13472-08-7) + 2-phenylimidazo[1,2-a]pyridine (4105-21-9) → 2-methyl-2-((2-phenylimidazo[1,2-a]pyridin-3-yl)thio)butanenitrile

Conditions	Yield
With sulfur; iodine In acetonitrile at 100℃; for 12h;	70%

azobis(2-cyanobutane) (13472-08-7) + diprop-2-ynyl Phthalate (48171-42-2) → bis(3-cyanoprop-2-ynyl) phthalate

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	68%

azobis(2-cyanobutane) (13472-08-7) + phenylacetylene (536-74-3) → 2-cyano-1-phenylacetylene (935-02-4)

Conditions	Yield
With copper(II) nitrate trihydrate In acetonitrile at 80℃; for 12h; Schlenk technique;	67%

Upstream product

• 4475-95-0 2-amino-2-methylbutanenitrile 
• 171915-82-5 2,2'-dimethyl-2,2'-hydrazo-di-butyronitrile 
• 79-10-7 acrylic acid 
• 4813-57-4 octadecylacrylate 
• 60-24-2 2-hydroxyethanethiol 
• 822-06-0 Hexamethylene diisocyanate 
• 16248-72-9 α-(N-Dichloramino)-s-valeronitril 

Downstream Products

• 74-90-8 hydrogen cyanide 
• 128903-20-8 2,3-diethyl-2,3-dimethyl-succinonitrile 
• 142617-32-1 C₁₁H₁₀Br₃N₂O 
• 503-74-2 3-methylbutyric acid 
• 1201634-58-3 3-[4-(trifluoromethyl)phenyl]-2-propynenitrile 
• 575433-43-1 3-(4-fluorophenyl)-2-propynenitrile 
• 49748-63-2 3-(4-chlorophenyl)-2-propynenitrile 
• 935-02-4 3-Phenyl-2-propynonitrile 
• 14677-99-7 3-(p-methoxyphenyl)-2-propynenitrile 
• 73606-42-5 3-(thiophen-3-yl)propiolonitrile 
• 110409-54-6 4-phenoxybut-2-ynenitrile 
• 861370-36-7 5-phenylpent-2-ynenitrile 
• 220182-83-2 1-cyano-1-methylpropyl dithiobenzoate 

Relevant articles and documents

Oxidation of alkylcyanohydrazines to azo-bis nitriles using Oxone-potassium bromide in aqueous medium

Azo-bis nitriles were prepared in good yields and high purity by oxidation of corresponding 1,2-bis-dialkylcyano hydrazines using oxone-potassium bromide in aqueous medium.

Azobisisobutyronitrile preparation method

The present invention relates to an azobisisobutyronitrile preparation method, which comprises: carrying out a reaction on sodium hypochlorite, ammonia and acetone to prepare an acetone azine synthesis solution; purifying to obtain acetone azine with a mass content of not less than 90%; reacting with hydrogen cyanide to obtain hydrogenated azobisisobutyronitrile; and oxidizing with chlorine gas orhydrogen peroxide to obtain an azobisisobutyronitrile solution. Compared to the conventional process, the method of the present invention can simplify the production process, shorten the production cycle, and reduce the consumption of steam and circulating water so as to increase the yield of azobisisobutyronitrile and reduce the production cost.

FLUORINATED ETHER URETHANES AND METHODS OF USING THE SAME

Compounds comprising end groups represented by formula (Rf-Q)a-X-(A-)b and compounds comprising the reaction product of components comprising a multifunctional isocyanate compound and a fluorinated compound represented by formula (Rf-Q)a-X—(Z)b. Each Rf is independently a partially fluorinated or fully fluorinated group selected from RfA(O)2CHL′-(CF2)n—; [RfB—(O)1—C(L)H—CF2—O]m—W—; CF3CFH—O—(CF2)p—; CF3—(O—CF2)Z—; and CF3—O—(CF2)3—O—CF—. Methods of making an article having a surface using the fluorinated compounds and treated articles are also disclosed.