2638-94-0Relevant articles and documents
Vollmert,Bolte
, p. 17,22 (1960)
Alfa Aesar
(H59611) 4,4'-Azobis(4-cyanovaleric acid), 98%, cont. ca 18% water
2638-94-0
25g
470.0CNY
Alfa Aesar
(H59611) 4,4'-Azobis(4-cyanovaleric acid), 98%, cont. ca 18% water
2638-94-0
100g
1419.0CNY
Aldrich
(11590) 4,4′-Azobis(4-cyanovalericacid) ≥98.0% (T)
2638-94-0
11590-25G
682.11CNY
Version: 1.0
Creation Date: Aug 13, 2017
Revision Date: Aug 13, 2017
Product name | 4,4'-Azobis(4-cyanovaleric acid) |
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Product number | - |
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Other names | NC 25 |
Identified uses | For industry use only. CBI |
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Uses advised against | no data available |
Emergency phone number | - |
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Service hours | Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours). |
More Details:2638-94-0 SDS
4,4'-dicyano-4,4'-azo-di-valeric acid
Conditions | Yield |
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With oxone; potassium bromide In water at 20℃; | 26% |
Conditions | Yield |
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With sulfuric acid; water; hydrazine Behandeln des Reaktionsgemisches mit Brom; optically inactive stereoisomer(ic) of mp: 111 degree; | |
With sulfuric acid; water; hydrazine Behandeln des Reaktionsgemisches mit Brom; optically inactive stereoisomer(ic) of mp: 128 degree; |
1-hydroxy-pyrrolidine-2,5-dione
4,4'-dicyano-4,4'-azo-di-valeric acid
4-Cyano-4-[1-cyano-3-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-1-methyl-propylazo]-4-methyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester
Conditions | Yield |
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With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 37h; | 98% |
With dicyclohexyl-carbodiimide In 1,4-dioxane at 15 - 20℃; for 16h; |
4,4'-dicyano-4,4'-azo-di-valeric acid
chloride of 4,4'-azo-bis(4-cyanopentanoic) acid chloride
Conditions | Yield |
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With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h; | 95.6% |
With thionyl chloride at 80℃; for 0.666667h; | 93% |
With phosphorus pentachloride In chloroform at 0 - 20℃; | 84% |
4,4'-dicyano-4,4'-azo-di-valeric acid
Conditions | Yield |
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In ethyl acetate for 18h; Inert atmosphere; Reflux; | 95.4% |
2-(N-tert-butoxycarbonylamino)ethanol
4,4'-dicyano-4,4'-azo-di-valeric acid
Conditions | Yield |
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With dmap In acetonitrile at 0 - 20℃; for 24h; | 95% |
Conditions | Yield |
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With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; Inert atmosphere; Darkness; | 92% |
4,4'-dicyano-4,4'-azo-di-valeric acid
bis(dodecylsulfanyl thiocarbonyl)disulfide
4-cyano-4-[(dodecylsulfanylthiocarbonyl)-sulfanyl]pentanoic acid
Conditions | Yield |
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In ethyl acetate for 16h; Heating / reflux; | 91% |
In ethyl acetate for 22h; Reflux; | 91% |
In ethyl acetate for 18h; Reflux; | 76% |
In ethyl acetate for 22h; Reflux; | 4.162 g |
With ethyl acetate for 20h; Reflux; |
Conditions | Yield |
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Stage #1: carbon disulfide; 1-thiopropane With potassium hydroxide In water; acetone at 20℃; for 2h; Stage #2: With p-toluenesulfonyl chloride In acetone for 1h; Stage #3: 4,4'-dicyano-4,4'-azo-di-valeric acid at 80℃; | 90% |
bis(ethylsulfanyl thiocarbonyl)disulfide
4,4'-dicyano-4,4'-azo-di-valeric acid
cyano-4-[(ethylsulfanylthiocarbonyl)sulfanyl]-4-methylbutanoic acid
Conditions | Yield |
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In ethyl acetate Reflux; Inert atmosphere; | 88% |
In ethyl acetate for 12h; Reflux; | 87% |
In ethyl acetate at 80℃; for 13h; Cooling with ice; Sealed tube; Inert atmosphere; | 82% |
Conditions | Yield |
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With 2,6-dimethylpyridine; trifluoroacetic anhydride In dichloromethane at 0℃; for 24h; Inert atmosphere; | 88% |
thiazolidine-2-thione
4,4'-dicyano-4,4'-azo-di-valeric acid
2-[1-cyano-1-methyl-4-oxo-4-(2-thioxo-thiazolidin-3-yl)-butylazo]-2-methyl-5-oxo-5-(2-thioxothiazolidin-3-yl)-pentanenitrile
Conditions | Yield |
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With dmap; dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃; | 86.3% |
Stage #1: thiazolidine-2-thione; 4,4'-dicyano-4,4'-azo-di-valeric acid With dmap In dichloromethane for 0.25h; Cooling with ice; Stage #2: With diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.25h; | 76.2% |
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran |
4,4'-dicyano-4,4'-azo-di-valeric acid
triphenylmethyl diethoxyphosphoryldithioformate
Conditions | Yield |
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In ethyl acetate for 15h; Heating; | 85% |
carbon disulfide
1-butanethiol
4,4'-dicyano-4,4'-azo-di-valeric acid
4(((butylthio)carbonthioyl)thio)-4-cyanopentanoic acid
Conditions | Yield |
---|---|
Stage #1: n-butanethiol With potassium hydroxide In water for 0.5h; Stage #2: carbon disulfide In water for 0.666667h; Stage #3: 4,4'-dicyano-4,4'-azo-di-valeric acid Further stages; | 85% |
polymer, obtained by reversible addition fragmentation chain-transfer; monomer(s): 4-cyanopentanoic acid dithiobenzoate
4,4'-dicyano-4,4'-azo-di-valeric acid
A
polymer, Mn (SEC) = 23500, PDI (SEC) = 1.05; monomer(s): 4-cyanopentanoic acid dithiobenzoate; 4,4'-azobis(4-cyanopentanoic acid)polymer, Mn (SEC) = 23500, PDI (SEC) = 1.05; monomer(s): 4-cyanopentanoic acid dithiobenzoate; 4,4'-azobis(4-cyanopentanoic acid)
B
4-cyano-4-(thiobenzoylthio)pentanoic acid
Conditions | Yield |
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In methanol at 80℃; for 3h; | A 82% B n/a |
Conditions | Yield |
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With propiononitrile at 90℃; | 80% |
4,4'-dicyano-4,4'-azo-di-valeric acid
2'-(2''-methylacryolyloxy)ethyl-β-D-galactopyranoside
4-cyano-4-(thiobenzoylthio)pentanoic acid
poly[2-(β-D-galactosyloxy)ethyl methacrylate], Mn (SEC) 24100, PDI (SEC) 1.09; monomer(s): 2-(β-D-galactosyloxy)ethyl methacrylate; 4,4-azobis(4-cyanopentanoic acid); 4-(cyanopentanoic acid)-4-dithiobenzoate
Conditions | Yield |
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In ethanol; water at 70℃; for 3h; | 80% |
bis(2-phenylethanesulfanylthiocarbonyl)disulfide
4,4'-dicyano-4,4'-azo-di-valeric acid
4-cyano-4-((2-phenylethylsulfanylthiocarbonyl)sulfanyl)pentanoic acid
Conditions | Yield |
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In ethyl acetate for 18h; Inert atmosphere; Reflux; | 78% |
In ethyl acetate for 18h; Inert atmosphere; Reflux; | 78% |
In ethyl acetate for 18h; Inert atmosphere; Reflux; |
bis-ethoxythiocarbonyldisulfane
4,4'-dicyano-4,4'-azo-di-valeric acid
4-cyano-4-((thioethoxyl)sulfanyl)pentanoic acid
Conditions | Yield |
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In 1,4-dioxane for 4h; Heating; | 77% |
4,4'-dicyano-4,4'-azo-di-valeric acid
1-hydroxy-2-phenyl-2-(4-tert-butoxycarbonylamino-2,2,6,6-tetramethyl-1-piperidinyloxy)ethane
Conditions | Yield |
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With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 8h; Ambient temperature; | 76% |
bis(thiobenzoyl) disulfide
4,4'-dicyano-4,4'-azo-di-valeric acid
4-cyano-4-(thiobenzoylthio)pentanoic acid
Conditions | Yield |
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In ethyl acetate at 85℃; for 12h; Inert atmosphere; | 75% |
In ethyl acetate for 18h; Heating; | 68% |
In ethyl acetate Reflux; | 65% |
4,4'-dicyano-4,4'-azo-di-valeric acid
Propargylamine
4-cyano-4-(1-cyano-3-ethynylcarbamoyl-1-methylpropylazo)-N-ethynyl-4-methylbutyramide
Conditions | Yield |
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Stage #1: 4,4'-dicyano-4,4'-azo-di-valeric acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: Propargylamine In N,N-dimethyl-formamide at 0 - 25℃; for 12.5h; Inert atmosphere; | 75% |
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling with ice; | 75% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; | 69% |
Stage #1: 4,4'-dicyano-4,4'-azo-di-valeric acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: Propargylamine In tetrahydrofuran at 20℃; for 4h; | 48% |
4,4'-dicyano-4,4'-azo-di-valeric acid
N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl
4-cyano-4-[N-tert-butyl-N-(1-diethoxyphosphoryl-2,2-dimethylpropyl)aminoxy]pentanoic acid
Conditions | Yield |
---|---|
In ethanol; water at 10℃; for 4h; UV-irradiation; | 70% |
3-azidopropan-1-ol
4,4'-dicyano-4,4'-azo-di-valeric acid
4,4'-azobis(3-azidopropyl 4-cyanopentanoate)
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 4 - 20℃; | 66% |
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 4 - 20℃; | 1.5 g |
4,4'-dicyano-4,4'-azo-di-valeric acid
1-hydroxy-2-phenyl-2-(2',2',6',6'-tetramethyl-1'-piperidinyloxy)ethane
Conditions | Yield |
---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 72h; | 65% |
Conditions | Yield |
---|---|
Stage #1: 4,4'-dicyano-4,4'-azo-di-valeric acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -4℃; for 1.5h; Inert atmosphere; Stage #2: 1-amino-3-(dimethylamino)propane In dichloromethane at -4 - 20℃; for 24h; Inert atmosphere; | 65% |
N-BOC-1,2-diaminoethane
4,4'-dicyano-4,4'-azo-di-valeric acid
(2-{4-[3-(2-tert-butoxycarbonylaminoethylcarbamoyl)-1-cyano-1-methylpropylazo]-4-cyano-4-methylbutyrylamino}-ethyl)carbamic acid tert-butyl ester
Conditions | Yield |
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With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; | 62% |
t-butoxycarbonylhydrazine
4,4'-dicyano-4,4'-azo-di-valeric acid
N′-[4-cyano-4-(1-cyano-1-methyl-3-methylcarbamoylpropylazo)-4-methylbutyryl]hydrazinecarboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; | 61% |
4,4'-dicyano-4,4'-azo-di-valeric acid
allyl alcohol
bisallyl 4,4'-azobis(4-cyanopentanoate)
Conditions | Yield |
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With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Darkness; | 60% |
4,4'-dicyano-4,4'-azo-di-valeric acid
1-aminooctadecane
4-cyano-4-(1-cyano-1-methyl-3-octadecylcarbamoyl-propylazo)-4-methyl-N-octadecyl-butyramide
Conditions | Yield |
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Stage #1: 4,4'-dicyano-4,4'-azo-di-valeric acid With dmap; triethylamine In dichloromethane for 0.25h; Stage #2: 1-aminooctadecane With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 18h; Further stages.; | 59% |
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 20℃; for 12h; | 46% |
4,4'-dicyano-4,4'-azo-di-valeric acid
4-cyano-4-(thiobenzoylthio)pentanoic acid
Conditions | Yield |
---|---|
With pyrrol-N-thiocarbonyl disulfides In ethyl acetate for 20h; | 59% |
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere 3: ethyl acetate / 20 h / 80 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Stage #1: 4,4'-dicyano-4,4'-azo-di-valeric acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Stage #2: 2-hydroxyethyl acrylate In dichloromethane | 54.1% |