2589-57-3

Basic information

• Product Name: Dimethyl 2,2'-azobis(2-methylpropionate)
• Synonyms: 2,2'-Azobis(methyl 2-methyl propionate);MAIB;2,2'-Azobis(methyl isobutyrate);2,2-AZOBISISOBUTYRIC ACID DIMETHYL ESTER 99%;Dimethyl 2,2’-azobis(2-methylpropionate):V-601;dimethyl 2,2'-azodiisobutyrate;2,2'-Azobis(2-methylpropanoic acid)dimethyl ester;2,2'-Azobis(2-methylpropionic acid)dimethyl ester
• CAS NO: 2589-57-3
• Molecular Formula: C₁₀H₁₈N₂O₄
• Molecular Weight: 230.26
• EINECS: 219-976-6
• Product Categories: pharmacetical
• Mol File: 2589-57-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 22-28°C
• Boiling Point: 248.3 ºCat 760 mmHg
• Flash Point: 77.7 ºC
• Appearance: white crystal(little light yellow)
• Density: 1.06 g/cm³
• Vapor Pressure: 2.85Pa at 20℃
• Water Solubility: insoluble
• CAS DataBase Reference: Dimethyl 2,2'-azobis(2-methylpropionate)(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 2,2'-azobis(2-methylpropionate)(2589-57-3)
• EPA Substance Registry System: Dimethyl 2,2'-azobis(2-methylpropionate)(2589-57-3)

Safety Data

• Hazardous Substances Data: 2589-57-3(Hazardous Substances Data)

Usage

General Description

Dimethyl 2,2'-azobis(2-methylpropionate) is a synthetic chemical compound, often used as a radical initiator due to its property of thermally decomposing into free radicals. These radicals are important in several chemical reactions, especially in polymerization processes where they initiate the formation of polymer chains. The compound is typically sold as a powder or granules and is highly sensitive to air, meaning it needs to be stored under inert gas. It has the molecular formula (C7H12O2)2N2 and is also known by the name V-044. As with many chemicals, it requires careful handling to avoid risks related to skin exposure or inhalation.

Synthetic route

methanol (67-56-1) + 2,2'-azobis(isobutyronitrile) (78-67-1) → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3)

Conditions	Yield
With thionyl chloride In 1,2-dichloro-ethane at 15 - 32℃; for 6h; Temperature; Solvent; Reagent/catalyst;	94.9%

methanol (67-56-1) + 2,2'-hydrazobis(2-methylpropionitrile) (6869-07-4) → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3)

Conditions	Yield
Stage #1: methanol; 2,2'-hydrazobis(2-methylpropionitrile) With chlorine; sodium bromide In chlorobenzene at 15℃; Stage #2: With hydrogenchloride In chlorobenzene at 20℃; for 18h; Stage #3: With water In toluene at 30℃; for 2h;	92%

methanol (67-56-1) + propyl cyanide (109-74-0) → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3)

Conditions	Yield
Stage #1: methanol; propyl cyanide In toluene at 20℃; for 0.0833333h; Stage #2: With hydrogenchloride In water; toluene at 10 - 20℃; for 1.05h; Temperature; Solvent;	80.3%

propyl cyanide (109-74-0) → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3)

Conditions	Yield
With hydrogenchloride In water; toluene at 18 - 22℃; for 18h; Large scale;	54.2%

methyl ester of α-(N-chloro-N-methoxyamino)isobutyric acid (76170-90-6) → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + dimethyl azoxyisobutyrate (80552-77-8)

Conditions	Yield
With sodium thioethylate In acetonitrile at 20℃; for 8h;	A 7.3% B 24.6%

methyl-α-N,N-dichloroaminoisobutyrate (34508-73-1) → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3)

Conditions	Yield
With sodium hydroxide In methanol

methanol (67-56-1) + Azobis(n-butylcarboxypropane) (21302-38-5) → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + butyl methyl azoisobutyrate

Conditions	Yield
With sodium hydride In benzene for 20h; Ambient temperature; Yields of byproduct given;	A n/a B 680 mg

dimethyl 2,2'-hydrazinobisisobutyrate (199590-95-9) + bromine water → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3)

water (7732-18-5) + dimethyl 2,2'-(diazene-1,2-diyl)bis(2-methylpropanimidate) dihydrochloride (52300-30-8, 52845-48-4) → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3)

methanol (67-56-1) + 2,2'-azobis(isobutyronitrile) (78-67-1) + ethanol (64-17-5) → C11H20N2O4 + dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + diethyl 2,2'-azobis(2-methylpropionate) (3879-07-0)

Conditions	Yield
Stage #1: methanol; 2,2'-azobis(isobutyronitrile); ethanol With hydrogenchloride In toluene at 15 - 20℃; for 20 - 21h; Stage #2: With water In toluene at 30℃; for 2h;
Stage #1: 2,2'-azobis(isobutyronitrile); ethanol With hydrogenchloride In toluene at 15 - 20℃; for 6h; Stage #2: methanol With hydrogenchloride In toluene at 15 - 20℃; for 17.5h; Stage #3: With water In toluene at 20 - 30℃; for 1h;

[α,α']azoisobutyrimidic acid dimethyl ester (74095-59-3) → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3)

Conditions	Yield
With water at 10 - 30℃; for 1h;

2-oxotetrahydrofuran-3-yl methacrylate (195000-66-9) + (2,4-dimethoxyphenyl)-[4'-(2-hydroxy-ethoxy)-phenyl]-dimethoxymethane → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3)

dimethyl 2,2'-hydrazinobisisobutyrate (199590-95-9) → dimethyl 2,2'-azobis(isobutyrate) (2589-57-3)

Conditions	Yield
With ammonium cerium (IV) nitrate; oxygen; acetic acid In 1,4-dioxane; water at 60℃; under 760.051 Torr; for 4h; Sealed tube;	70 %Chromat.

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + divinyl adipate (4074-90-2) → polymer; monomer(s): divinyl adipate, 0.3 mol/l; dimethyl 2,2\-azobis(isobutyrate), 0.01 mol/l

Conditions	Yield
In benzene at 80℃; for 4h;	93%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + N-methyl-N-(2-methylprop-2-enoyl)benzamide (111875-47-9) → methyl 3-(2,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-4-yl)-2,2-dimethylpropanoate

Conditions	Yield
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 90℃;	92%
With potassium phosphate; copper(l) iodide; oxygen In N,N-dimethyl-formamide at 90℃; under 760.051 Torr;	57%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + 2-(1-azidovinyl)-4'-chloro-1,1'-biphenyl → methyl 2,2-dimethyl-3-(3-chlorophenanthridin-6-yl)propanoate

Conditions	Yield
With copper(II) nitrate nonahydrate In N,N-dimethyl-formamide at 50℃; for 8h; Reagent/catalyst; Temperature; Inert atmosphere;	92%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + 3,4,5‐trihydroxycinnamic acid (6093-59-0) → 2,2-dimethyl-4-(3,4,5-trihydroxyphenyl)-3-butenoic acid methyl ester

Conditions	Yield
With silver trifluoromethanesulfonate; p-toluidine; copper(II) oxide at 120℃; for 9h;	89%
at 120℃; for 9h;
at 120℃; for 9h; Temperature; Reagent/catalyst;

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + trans-3-(3,4,5-trihydroxyphenyl)-2-propenoic acid (6093-59-0) → 2,2-dimethyl-4-(3,4,5-trihydroxyphenyl)-3-butenoic acid methyl ester

Conditions	Yield
With silver trifluoromethanesulfonate; p-toluidine; copper(II) oxide at 120℃; for 9h; Temperature; Reagent/catalyst;	89%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + divinyl adipate (4074-90-2) → polymer, Mn 1.68E4 g/mol by GPC, Mw/Mn 13.0; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

Conditions	Yield
In benzene at 80℃; for 4h;	87%

3-pyridin-2-yl-acrylic acid (7340-22-9) + dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) → (E)-methyl 2,2-dimethyl-4-(pyridin-2-yl)but-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	85%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + 2-(1-vinyl azide)-4'-methyl-1,1'-biphenyl → C20H21NO2

Conditions	Yield
With copper(II) nitrate nonahydrate In dichloromethane at 100℃; for 8h; Temperature; Solvent; Inert atmosphere;	85%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + 3-(4-chlorobenzoyl)acrylic acid (29582-39-6, 6269-33-6) → (E)-methyl 5-(4-chlorophenyl)-2,2-dimethyl-5-oxopent-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	84%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + (Z)-4-(2,5-Dimethyl-phenyl)-4-oxo-but-2-enoic acid (15254-22-5) → (E)-methyl 5-(2,5-dimethylphenyl)-2,2-dimethyl-5-oxopent-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	83%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + Cinnamic acid (621-82-9) → methyl (E)-2,2-dimethyl-4-phenyl-3-buten-1-oate (94041-88-0)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Reagent/catalyst; Time; Inert atmosphere;	83%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + di-isopropyl azodicarboxylate (2446-83-5) + 1-ethynyl-3-methoxybenzene (768-70-7) → diisopropyl 1-[(E)-1-(3-methoxyphenyl)-4-methoxy-3,3-dimethyl-4-oxobut-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;	83%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + β-(4-bromobenzoyl)acrylic acid (39644-80-9) → (E)-methyl 5-(4-bromophenyl)-2,2-dimethyl-5-oxopent-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	82%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + 3-benzoylacrylic acid (583-06-2) → (E)-methyl 2,2-dimethyl-5-oxo-5-phenylpent-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	80%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + divinyl adipate (4074-90-2) → polymer, Mn 1.85E4 g/mol by GPC, Mw/Mn 12.7; monomer(s): divinyl adipate; dimethyl 2,2\-azobis(isobutyrate)

Conditions	Yield
In benzene at 80℃; for 4h;	79%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + N-phenyl-N-(prop-2- yn-1-yl)methacrylamide (1242029-32-8) → methyl 2,2-dimethyl-3-(3-methyl-4-methylene-2-oxo-1-phenylpyrrolidin-3-yl)propanoate

Conditions	Yield
In ethyl acetate at 60℃; for 16h; Schlenk technique; Green chemistry; regioselective reaction;	78%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + 3-methylcinnamic acid (3029-79-6) → (E)-methyl 2,2-dimethyl-4-m-tolylbut-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	77%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + 4-(p-methylphenyl)-4-oxo-2-butenoic acid (20972-36-5, 35513-41-8, 24849-45-4) → (E)-methyl 2,2-dimethyl-5-oxo-5-p-tolylpent-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	77%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + di-isopropyl azodicarboxylate (2446-83-5) + 4-methoxyphenylacetylen (768-60-5) → diisopropyl 1-[(E)-4-methoxy-1-(4-methoxyphenyl)-3,3-dimethyl-4-oxobut-1-en-1-yl]-1,2-hydrazinedicarboxylate

Conditions	Yield
With copper(I) bromide In acetonitrile at 80℃; for 8h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; stereoselective reaction;	77%

3,4-methylenedioxyphenylethyne (57134-53-9) + dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + di-isopropyl azodicarboxylate (2446-83-5) → diisopropyl 1-[(E)-1-(benzo[d][1,3]dioxol-5-yl)-4-methoxy-3,3-dimethyl-4-oxobut-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;	77%

3,4,5-trimethoxycinnamic acid (90-50-6) + dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) → (E)-methyl 2,2-dimethyl-4-(3,4,5-trimethoxyphenyl)but-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	76%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + cis-cinnamic acid (140-10-3, 621-82-9, 102-94-3) → methyl (E)-2,2-dimethyl-4-phenyl-3-buten-1-oate (94041-88-0)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	76%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + α-phenylselenylacrylonitrile (78811-30-0) → (E)-4,5-Bis-methoxycarbonyl-2,2,7,7-tetramethyl-oct-4-enedioic acid dimethyl ester

Conditions	Yield
In benzene at 80℃; for 16h;	75%

p-chlorocinnamic acid (1615-02-7) + dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) → (E)-methyl 4-(4-chlorophenyl)-2,2-dimethylbut-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	75%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + 2-methylcinnamic acid (2373-76-4) → (E)-methyl 2,2-dimethyl-4-o-tolylbut-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	73%

3-ethynylquinoline (78593-40-5) + dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + di-isopropyl azodicarboxylate (2446-83-5) → diisopropyl 1-[(E)-4-methoxy-3,3-dimethyl-4-oxo-1-(quinolin-3-yl)but-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;	73%

Upstream product

• 199590-95-9 dimethyl 2,2'-hydrazinobisisobutyrate 
• 67-56-1 methanol 
• 34241-39-9 azobisisobutyronitrile 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 
• 52300-30-8 2,2'-azobis(1-imino-1-methoxy-2-methylpropane) dihydrochloride 
• 109-74-0 propyl cyanide 
• 195000-66-9 2-oxotetrahydrofuran-3-yl methacrylate 
• 6869-07-4 2,2'-hydrazobis(2-methylpropionitrile) 
• 74095-59-3 [α,α']azoisobutyrimidic acid dimethyl ester 
• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 52300-30-8 dimethyl 2,2'-(diazene-1,2-diyl)bis(2-methylpropanimidate) dihydrochloride 
• 76170-90-6 methyl ester of α-(N-chloro-N-methoxyamino)isobutyric acid 

Downstream Products

• 856637-53-1 N,O-bis-(1-methoxycarbonyl-1-methyl-ethyl)-N-phenyl-hydroxylamine 
• 67648-64-0 2-(4-Hydroxyphenoxy)-2-methyl-propionic acid 
• 20924-10-1 2,2,3-Trimethyl-3-[2-(methyl-phenyl-amino)-ethyl]-succinic acid dimethyl ester 
• 150-60-7 dibenzyl disulphide 
• 547-63-7 Methyl isobutyrate 
• 111-84-2 nonane 
• 64935-41-7 (E)-2-octyl-3-nonylacrolein 
• 110-54-3 hexane 
• 64935-39-3 (E)-2-hexyldec-2-enal 
• 142-82-5 n-heptane 
• 540-84-1 2,2,4-trimethylpentane 
• 65563-98-6 2-benzoylamino-2-methyl-propionic acid methyl ester 
• 109365-57-3 N,O-bis-(hydroxy-tert-butyl)-N-phenyl-hydroxylamine 
• 111328-05-3 N,O-bis-(1-carboxy-1-methyl-ethyl)-N-phenyl-hydroxylamine 

Relevant articles and documents

Method for continuously preparing dimethyl azodiisobutyrate by using micro-channel reactor

The invention discloses a method for continuously preparing dimethyl azodiisobutyrate by using a micro-channel reactor, which comprises the following steps: 1, heating butyronitrile, and dissolving the butyronitrile in a benzene solvent to obtain a mixed solution with the mass concentration of butyronitrile of 5-30%; inputting the mixed solution and methanol into a first mixing zone of a micro-channel reactor for mixing to obtain a first mixed material; 2, mixing the mixed material and hydrogen chloride gas in a second mixing zone of a micro-channel reactor, and introducing the mixture into the micro-channel reactor for primary reaction; and 3, mixing the reaction solution after the heat preservation reaction with water, introducing the mixture into a micro-channel reactor, carrying out asecondary reaction, standing, performing centrifuging to obtain a crude product of dimethyl azobisisobutyrate after the reaction is finished, and performing recrystallizing to obtain dimethyl azobisisobutyrate. According to the method, the reaction rate and the raw material utilization rate are increased, the batch quality difference caused by reaction temperature fluctuation is avoided, the reaction is easy to control, the production period is short, and the total yield can reach 75% or above.

2,2'-azo(2-methyl-N-(2-hydroxyethyl)propionamide) preparation method

The invention discloses a 2,2'-azo(2-methyl-N-(2-hydroxyethyl)propionamide) preparation method, which comprises: adding 2,2'-azobisisobutyronitrile, methanol and toluene to a reactor having a stirring and reflux device, starting stirring, slowly introducing hydrogen chloride gas under cooling, and controlling the temperature of the material and carrying out a thermal insulation reaction; after completing the reaction, adding the reaction liquid into water in a dropwise manner, carrying out a hydrolysis reaction, layering after completing the hydrolysis, adding a small amount of methanol to the organic phase, and carrying out pressure reducing distillation for a certain time; after completing the distillation, slowly adding the organic phase into a mixed solution of sodium methoxide and monoethanolamine in a dropwise manner, and carrying out thermal insulation; after completing the thermal insulation, carrying out solid-liquid separation by a centrifuge, continuously washing the solid with water, crystallizing, carrying out centrifugation until the material is dried, placing the material in a drying device, and drying; and after the drying, cooling the material to a normal temperature to obtain the 2,2'-azo(2-methyl-N-(2-hydroxyethyl)propionamide) product, wherein the product content (HPLC) is more than 98%, and the yield is 55-75%.

METHOD FOR PRODUCING AZO COMPOUNDS

PROBLEM TO BE SOLVED: To provide a method that can produce azo compounds at good yields by making oxygen or an oxygen-containing gas act on hydrazo groups of hydrazo compounds when oxidatively dehydrogenating them. SOLUTION: Azo compounds are produced by making oxygen or an oxygen-containing gas act on hydrazo compounds in the presence of vanadium or cerium compounds, and a solvent. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT