4,4'-Azobis(4-cyanovaleric acid) supplier

Name
4,4'-Azobis(4-cyanovaleric acid)
EINECS 220-135-0
CAS No. 2638-94-0
Article Data3
CAS DataBase
Density 1.23 g/cm³
Solubility Soluble in water.
Melting Point 118-125 °C (dec.)(lit.)
Formula C₁₂H₁₆N₄O₄
Boiling Point 503.6 °C at 760 mmHg
Molecular Weight 280.283
Flash Point 258.3 °C
Transport Information UN 1325 4.1/PG 2
Appearance white crystalline powder
Safety 15-16-22-24/25-36
Risk Codes 11
Molecular Structure
Hazard Symbols F
Synonyms Pentanoicacid, 4,4'-azobis[4-cyano- (9CI);Valeric acid, 4,4'-azobis[4-cyano- (6CI,8CI);4,4'-Azobis(4-cyanopentanecarboxylic acid);4,4'-Azobis(cyanovaleric acid);4,4'-Azobis[4-cyanopentanoic acid];4,4'-Azobis[4-cyanovaleric acid];ABCVA;ACV-A;Azobis(cyanovaleric acid);NSC 114466;V 501;VA 501;Vazo 68;Vazo68WSP;
PSA 146.90000
LogP 1.73276

Synthetic route

: 4,4'-hydrazo-bis-4-cyano-pentanoic acid

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

Conditions

Conditions	Yield
With oxone; potassium bromide In water at 20℃;	26%

: 143-33-9
sodium cyanide

: 123-76-2
levulinic acid

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

Conditions

Conditions	Yield
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;

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 130468-55-2
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

Conditions	Yield
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;

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 17170-81-9
chloride of 4,4'-azo-bis(4-cyanopentanoic) acid chloride

Conditions

Conditions	Yield
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%

: bis(9H-carbazole-9-yl-thiocarbonyl)disulfide

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: C19H16N2O2S2

Conditions

Conditions	Yield
In ethyl acetate for 18h; Inert atmosphere; Reflux;	95.4%

: 26690-80-2
2-(N-tert-butoxycarbonylamino)ethanol

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: bis(2-((tert-butoxycarbonyl)amino)ethyl)(4,4-azobis(4-cyanovalerate))

Conditions

Conditions	Yield
With dmap In acetonitrile at 0 - 20℃; for 24h;	95%

: 821-09-0
n-Pent-4-enyl alcohol

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: C22H32N4O4

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; Inert atmosphere; Darkness;	92%

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 870532-86-8
bis(dodecylsulfanyl thiocarbonyl)disulfide

: 870196-80-8
4-cyano-4-[(dodecylsulfanylthiocarbonyl)-sulfanyl]pentanoic acid

Conditions

Conditions	Yield
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;

: 75-15-0
carbon disulfide

: 107-03-9
1-thiopropane

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 4-cyano-4-[(propylsulfanylthiocarbonyl)sulfanyl]pentanoic acid

Conditions

Conditions	Yield
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%

...Expand

: 10219-97-3
bis(ethylsulfanyl thiocarbonyl)disulfide

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 1137725-46-2
cyano-4-[(ethylsulfanylthiocarbonyl)sulfanyl]-4-methylbutanoic acid

Conditions

Conditions	Yield
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%

: 771-61-9
2,3,4,5,6-pentafluorophenol

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: bis(pentafluorophenyl)azobis(4-cyanovalerate)

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; trifluoroacetic anhydride In dichloromethane at 0℃; for 24h; Inert atmosphere;	88%

: 134469-06-0
thiazolidine-2-thione

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 870779-03-6
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

Conditions	Yield
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

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 178878-92-7
triphenylmethyl diethoxyphosphoryldithioformate

: 4-carboxy-2-cyanobut-2-yl diethoxyphosphoryldithioformate

Conditions

Conditions	Yield
In ethyl acetate for 15h; Heating;	85%

: 75-15-0
carbon disulfide

: 109-79-5
1-butanethiol

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 937162-86-2
4(((butylthio)carbonthioyl)thio)-4-cyanopentanoic acid

Conditions

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%

...Expand

polymer, obtained by reversible addition fragmentation chain-transfer; monomer(s): 4-cyanopentanoic acid dithiobenzoate: polymer, obtained by reversible addition fragmentation chain-transfer; monomer(s): 4-cyanopentanoic acid dithiobenzoate

: 2638-94-0
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: 201611-92-9
4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions

Conditions	Yield
In methanol at 80℃; for 3h;	A 82% B n/a

...Expand

: 100-42-5
styrene

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

polymer: polymer

Conditions

Conditions	Yield
With propiononitrile at 90℃;	80%

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 21698-14-6
2'-(2''-methylacryolyloxy)ethyl-β-D-galactopyranoside

: 201611-92-9
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: 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

Conditions	Yield
In ethanol; water at 70℃; for 3h;	80%

...Expand

: 1351859-45-4
bis(2-phenylethanesulfanylthiocarbonyl)disulfide

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 1351859-46-5
4-cyano-4-((2-phenylethylsulfanylthiocarbonyl)sulfanyl)pentanoic acid

Conditions

Conditions	Yield
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;

: 502-55-6
bis-ethoxythiocarbonyldisulfane

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 220575-22-4
4-cyano-4-((thioethoxyl)sulfanyl)pentanoic acid

Conditions

Conditions	Yield
In 1,4-dioxane for 4h; Heating;	77%

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 213994-50-4
1-hydroxy-2-phenyl-2-(4-tert-butoxycarbonylamino-2,2,6,6-tetramethyl-1-piperidinyloxy)ethane

: 4-{3-[2-(4-tert-Butoxycarbonylamino-2,2,6,6-tetramethyl-piperidin-1-yloxy)-2-phenyl-ethoxycarbonyl]-1-cyano-1-methyl-propylazo}-4-cyano-4-methyl-butyric acid 2-(4-tert-butoxycarbonylamino-2,2,6,6-tetramethyl-piperidin-1-yloxy)-2-phenyl-ethyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 8h; Ambient temperature;	76%

: 5873-93-8
bis(thiobenzoyl) disulfide

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 201611-92-9
4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions

Conditions	Yield
In ethyl acetate at 85℃; for 12h; Inert atmosphere;	75%
In ethyl acetate for 18h; Heating;	68%
In ethyl acetate Reflux;	65%

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 2450-71-7
Propargylamine

: 1256812-46-0
4-cyano-4-(1-cyano-3-ethynylcarbamoyl-1-methylpropylazo)-N-ethynyl-4-methylbutyramide

Conditions

Conditions	Yield
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%

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 188526-94-5
N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl

: 1034133-00-0
4-cyano-4-[N-tert-butyl-N-(1-diethoxyphosphoryl-2,2-dimethylpropyl)aminoxy]pentanoic acid

Conditions

Conditions	Yield
In ethanol; water at 10℃; for 4h; UV-irradiation;	70%

: 72320-38-8
3-azidopropan-1-ol

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 1280212-00-1
4,4'-azobis(3-azidopropyl 4-cyanopentanoate)

Conditions

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

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 161776-41-6
1-hydroxy-2-phenyl-2-(2',2',6',6'-tetramethyl-1'-piperidinyloxy)ethane

: 4-Cyano-4-{1-cyano-1-methyl-3-[2-phenyl-2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-ethoxycarbonyl]-propylazo}-4-methyl-butyric acid 2-phenyl-2-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-ethyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 72h;	65%

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 109-55-7
1-amino-3-(dimethylamino)propane

: DABPA

Conditions

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%

: 57260-73-8
N-BOC-1,2-diaminoethane

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 1426244-88-3
(2-{4-[3-(2-tert-butoxycarbonylaminoethylcarbamoyl)-1-cyano-1-methylpropylazo]-4-cyano-4-methylbutyrylamino}-ethyl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h;	62%

: 870-46-2
t-butoxycarbonylhydrazine

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 1426244-85-0
N′-[4-cyano-4-(1-cyano-1-methyl-3-methylcarbamoylpropylazo)-4-methylbutyryl]hydrazinecarboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h;	61%

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 107-18-6
allyl alcohol

: 124334-87-8
bisallyl 4,4'-azobis(4-cyanopentanoate)

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Darkness;	60%

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 124-30-1
1-aminooctadecane

: 939437-81-7
4-cyano-4-(1-cyano-1-methyl-3-octadecylcarbamoyl-propylazo)-4-methyl-N-octadecyl-butyramide

Conditions

Conditions	Yield
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%

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 201611-92-9
4-cyano-4-(thiobenzoylthio)pentanoic acid

Conditions

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

: 2638-94-0
4,4'-dicyano-4,4'-azo-di-valeric acid

: 818-61-1
2-hydroxyethyl acrylate

: C22H28N4O8

Conditions

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%

4,4'-Azobis(4-cyanovaleric acid) Chemical Properties

IUPAC Name: 4-cyano-4-(2-cyano-5-hydroxy-5-oxopentan-2-yl)diazenylpentanoic acid
Synonyms of 4,4'-Azobis(4-cyanopentanoic acid) (CAS NO.2638-94-0): 4,4'-Azobis(4-cyanovaleric acid) ; Azobis(cyanovaleric acid) ; Kyselina 4,4'-azo-bis-(4-kyanvalerova)
CAS NO: 2638-94-0
Molecular Formula: C₁₂H₁₆N₄O₄
Molecular Weight: 280.28
Molecular Structure:
EINECS: 220-135-0
H bond acceptors: 8
H bond donors: 2
Freely Rotating Bonds: 8
Polar Surface Area: 124.9 Å²
Index of Refraction: 1.546
Molar Refractivity: 71.88 cm³
Molar Volume: 226.9 cm³
Surface Tension: 51.8 dyne/cm
Density: 1.23 g/cm³
Flash Point: 258.3 °C
Enthalpy of Vaporization: 84.6 kJ/mol
Boiling Point: 503.6 ^oC at 760 mmHg
Vapour Pressure: 1.66E-11 mmHg at 25 °C
Melting point: 118-125 °C (dec.)(lit.)
Storage temp: 2-8°C
Appearance: white crystalline powder
Product Categories of 4,4'-Azobis(4-cyanopentanoic acid) (CAS NO.2638-94-0): Industrial/Fine Chemicals;Organic acids
SMILES: N#CC(/N=N/C(C#N)(CCC(=O)O)C)(C)CCC(=O)O
InChI: InChI=1/C12H16N4O4/c1-11(7-13,5-3-9(17)18)15-16-12(2,8-14)6-4-10(19)20/h3-6H2,1-2H3,(H,17,18)(H,19,20)/b16-15+
InChIKey: VFXXTYGQYWRHJP-FOCLMDBBBS
Std. InChI: InChI=1S/C12H16N4O4/c1-11(7-13,5-3-9(17)18)15-16-12(2,8-14)6-4-10(19)20/h3-6H2,1-2H3,(H,17,18)(H,19,20)/b16-15+
Std. InChIKey: VFXXTYGQYWRHJP-FOCLMDBBSA-N

4,4'-Azobis(4-cyanovaleric acid) Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	666mg/kg (666mg/kg)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 922, 1986.

4,4'-Azobis(4-cyanovaleric acid) Consensus Reports

Reported in EPA TSCA Inventory.

4,4'-Azobis(4-cyanovaleric acid) Safety Profile

Safety Information about 4,4'-Azobis(4-cyanopentanoic acid) (CAS NO.2638-94-0):
Hazard Codes: F
Risk Statements: 11
R11: Highly flammable.
Safety Statements: 15-16-22-24/25-36
S15: Keep away from heat.
S16: Keep away from sources of ignition.
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
S36: Wear suitable protective clothing.
RIDADR: UN 1325 4.1/PG 2
WGK Germany: 2
RTECS: YV6190500
F: 4.4-8
Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of NO_x.

Product Name

4,4'-Azobis(4-cyanovaleric acid)

Synthetic route

4,4'-Azobis(4-cyanovaleric acid) Chemical Properties

4,4'-Azobis(4-cyanovaleric acid) Toxicity Data With Reference

4,4'-Azobis(4-cyanovaleric acid) Consensus Reports

4,4'-Azobis(4-cyanovaleric acid) Safety Profile

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