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

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

 EINECS 220-135-0
CAS No. 2638-94-0 Density 1.23 g/cm3
PSA 146.90000 LogP 1.73276
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 Molecular Structure of 2638-94-0 (4,4'-Azobis(4-cyanovaleric acid)) Hazard Symbols FlammableF
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;

Article Data 3

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

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

2638-94-0

4,4'-dicyano-4,4'-azo-di-valeric acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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
ConditionsYield
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%

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: FlammableF
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 NOx.

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