4,4'-AZOBIS(4-CYANOVALERIC ACID)

4,4'-Azobis(4-cyanovaleric acid) is a functional azo initiator widely used to generate free radicals for polymerization reactions.
4,4'-Azobis(4-cyanovaleric acid)'s carboxylic acid groups make it especially useful in the synthesis of functional polymers, copolymers, and surface-modified polymer materials.
4,4'-Azobis(4-cyanovaleric acid) is valued for its controlled thermal decomposition, predictable radical generation, and versatility in both polymer chemistry and research applications.

CAS Number: 2638-94-0
EC Number: 220-135-0
Molecular Formula: C12H16N4O4
Molecular Weight: 280.28 g/mol

Synonyms: 2638-94-0, 4,4-Azobis(4-cyanovaleric acid), Pentanoic acid, 4,4'-azobis(4-cyano-, Pentanoic acid, 4,4'-azobis[4-cyano-, RefChem:1069318, 4,4'-Azobis(4-cyanovaleric acid), 4,4'-(Diazene-1,2-diyl)bis(4-cyanopentanoic acid), Azobis(cyanovaleric acid), 4,4'-Azobis(4-cyanopentanoic acid), ACVA, C12H16N4O4, ABCVA, DTXSID3044629, 4,4'-azobis-(4-cyanovaleric acid), Pentanoic acid, 4,4'-(1,2-diazenediyl)bis[4-cyano-, 1041193-98-9, 4-[(4-carboxy-2-cyanobutan-2-yl)diazenyl]-4-cyanopentanoic acid, 4,4'-Azobis-4-cyanovaleric acid, 4,4'-Diazene-1,2-diylbis(4-cyanopentanoic acid), 4,4'-Azobis[4-cyanopentanoic acid], MFCD00002799, NSC114466, (E)-4,4'-(diazene-1,2-diyl)bis(4-cyanopentanoic acid), 4,4'-Azobis[4-cyanovaleric acid], 4,4?-Azobis(4-cyanovaleric Acid), EINECS 220-135-0, Pentanoic acid, 4,4'-(1,2-diazenediyl)bis(4-cyano-, NSC 114466, Valeric acid, 4,4'-azobis(4-cyano-, BRN 1729856, 4-[(3-carboxy-1-cyano-1-methylpropyl)diazenyl]-4-cyanopentanoic acid, Kyselina 4,4'-azo-bis-(4-kyanvalerova) [Czech], 4,4'-Azobis(4-cyanovaleric) acid, 4-[2-(3-carboxy-1-cyano-1-methylpropyl)diazen-1-yl]-4-cyano-4-methylbutanoic acid, 4,4'-Azo-bis(4-cyanopentanoic acid), Kyselina 4,4'-azo-bis-(4-kyanvalerova), 4,4'-AZO-bis(4-CYANOVALERIC ACID), V-501, SCHEMBL27672, SCHEMBL27673, 4-04-00-03382 (Beilstein Handbook Reference), SCHEMBL786277, CHEMBL3185815, DTXCID1024629, DTXSID00859752, VFXXTYGQYWRHJP-FOCLMDBBSA-N, Valeric acid,4'-azobis[4-cyano-, 4-(3-carboxy-1-cyano-1-methyl-propyl)azo-4-cyano-pentanoic acid, Pentanoic acid,4'-azobis[4-cyano-, Tox21_302513, SBB058100, 4,4\'-Azobis(4-cyanovaleric acid), AKOS015853607, AKOS024348893, AC-1880, CS-W012275, FS-4446, NSC-114466, cis-4,4'-Azobis(4-cyanovaleric acid), NCGC00256797-01, FD155718, LS-14095, CAS-2638-94-0, 4,4'-Diazenediylbis(4-cyanopentanoic acid), A1671, ST50826085, EN300-1705965, F212738, 4,4'-[(E)-Diazenediyl]bis(4-cyanopentanoic acid), Q4637047, W-107175, 4,4'-Azobis(4-cyanovaleric acid), >=98.0% (T), 4,4'-(1E)-1,2-Diazenediylbis[4-cyanopentanoic acid], 4,4'-(Diazene-1,2-diyl)bis(4-cyanopentanoic acid) (contains 13-18% water), 4,4'-(Diazene-1,2-diyl)bis(4-cyanopentanoic acid) (contains up to 18% water), 4-cyano-4-[(E)-(1-cyano-4-hydroxy-1-methyl-4-oxo-butyl)azo]pentanoic acid, 4-[(E)-2-(3-CARBOXY-1-CYANO-1-METHYLPROPYL)DIAZEN-1-YL]-4-CYANO-4-METHYLBUTANOIC ACID

4,4'-Azobis(4-cyanovaleric acid) is a free radical initiator used in polymer synthesis.
4,4'-Azobis(4-cyanovaleric acid) is a water-soluble initiator used in both heterogeneous and homogeneous free-radical polymerizations.

4,4'-Azobis(4-cyanovaleric acid) is used as an initiator in reversible addition−fragmentation chain transfer polymerization (RAFT).
When heated to decomposition, c. 70 °C, 4,4'-Azobis(4-cyanovaleric acid) releases N2 and produces 2 equivalents of reactive radicals capable of initiating polymerization.

4,4'-Azobis(4-cyanovaleric acid) is a chemical compound that serves as a radical initiator in polymerization processes.
4,4'-Azobis(4-cyanovaleric acid) is characterized by its azo functional group, which is responsible for its ability to decompose thermally to generate free radicals.

This property makes 4,4'-Azobis(4-cyanovaleric acid) particularly useful in the production of polymers and copolymers, especially in the synthesis of acrylics and other vinyl polymers.
4,4'-Azobis(4-cyanovaleric acid) is typically a white to pale yellow solid and is soluble in organic solvents.

4,4'-Azobis(4-cyanovaleric acid) is known for its stability under normal conditions but decomposes upon heating, releasing nitrogen gas and generating radicals that initiate polymerization reactions.
Safety considerations include handling it with care, as 4,4'-Azobis(4-cyanovaleric acid) can be an irritant and poses risks associated with the generation of free radicals.

4,4'-Azobis(4-cyanovaleric acid)'s applications extend beyond polymer chemistry, including use in various industrial processes where controlled radical generation is required.
Proper storage and handling protocols are essential to ensure safety and efficacy in its applications.

4,4'-Azobis(4-cyanovaleric acid) is a critical chemical compound widely recognized as a water-soluble azo initiator.
4,4'-Azobis(4-cyanovaleric acid)'s primary function is to initiate free radical polymerization processes, making it indispensable for the synthesis of a wide variety of polymers, including but not limited to polyvinyl chloride, polyacrylonitrile, and polyvinyl alcohol.
The presence of carboxyl groups also allows for post-polymerization modifications, offering enhanced versatility in material design.

4,4'-Azobis(4-cyanovaleric acid) is an organic azo compound commonly used as a free-radical initiator in polymerization and chemical synthesis.
Upon controlled thermal decomposition, 4,4'-Azobis(4-cyanovaleric acid) generates radicals that can initiate polymerization reactions in suitable monomer systems.

4,4'-Azobis(4-cyanovaleric acid)'s carboxylic acid groups make it useful in the preparation of functional polymers, polymer particles, and surface-modified materials.
4,4'-Azobis(4-cyanovaleric acid) has also been used experimentally as a radical generator in oxidation and lipid-peroxidation studies.

4,4'-Azobis(4-cyanovaleric acid), short for ACVA, CAS No. 2638-94-0.
4,4'-Azobis(4-cyanovaleric acid)'s molecular formula is C12H16N4O4, molecular weight 280.28.

4,4'-Azobis(4-cyanovaleric acid) is a white crystalline powder under normal temperature and pressure, relative density is about 1.23g/cm³.
4,4'-Azobis(4-cyanovaleric acid) is an important organic compound, mainly used as a polymer initiator, can be used in polyvinyl chloride, polyacrylonitrile, polyvinyl alcohol, synthetic fiber optics and other polymers, but also can be used in plastics and synthetic rubber foaming agent.

In addition, 4,4'-Azobis(4-cyanovaleric acid) is a commonly used water-soluble radical initiator for the preparation of bentonite clay, modification of inorganic nanoparticle-coated polymers, and as a source of free radicals in kinetic surveys, an effective photosensitizer in the near-ultraviolet region, and a scavenger of oxygen in aqueous media.
In terms of safety, 4,4'-Azobis(4-cyanovaleric acid) is a hazardous material, hazard class 4.1, highly flammable, and needs to be ventilated, low-temperature and dry when stored, and transported in accordance with relevant regulations.

4,4'-Azobis(4-cyanovaleric acid) is used as a free radical imitator in polymer synthesis such as polyvinyl chloride, polyacrylonitrile, polyvinyl alcohol and synthetic fibers.
4,4'-Azobis(4-cyanovaleric acid) is utilized for both heterogeneous and homogenous free-radical polymerizations, and as an initiator in reversible addition-fragmentation chain transfer polymerization (RAFT).
4,4'-Azobis(4-cyanovaleric acid) is also used as a blowing agent for plastics and elastomers.

4,4'-Azobis(4-cyanovaleric acid), holds a prominent position as an organic compound.
Manifesting as a colorless, crystalline solid, 4,4'-Azobis(4-cyanovaleric acid) exhibits high solubility in both water and organic solvents.

Scientific research extensively utilizes 4,4'-Azobis(4-cyanovaleric acid)′-Azo-CVA for a multitude of purposes.
4,4'-Azobis(4-cyanovaleric acid)'s versatility as a reagent finds particular use in the synthesis of organic and inorganic compounds.

Furthermore, 4,4'-Azobis(4-cyanovaleric acid) plays a role in the production of polymers and other materials.
4,4'-Azobis(4-cyanovaleric acid)′-Azo-CVA boasts highly reactive properties, enabling it to partake in a diverse array of chemical reactions.

Among these, the azo coupling reaction stands as the most prevalent.
This reaction entails the coupling of two molecules of 4,4'-Azobis(4-cyanovaleric acid)′-Azo-CVA to generate a novel compound.
4,4'-Azobis(4-cyanovaleric acid) is used as a free radical imitator in polymer synthesis such as polyvinyl chloride, polyacrylonitrile, polyvinyl alcohol and synthetic fibers.

Applications of 4,4'-Azobis(4-Cyanovaleric Acid):
4,4'-Azobis(4-cyanovaleric acid) has been used in the preparation of polystyrene particles by polymerizing styrene in ethyl alcohol.
4,4'-Azobis(4-cyanovaleric acid) is used as a free radical imitator in polymer synthesis such as polyvinyl chloride, polyacrylonitrile, polyvinyl alcohol and synthetic fibers.

4,4'-Azobis(4-cyanovaleric acid) is utilized for both heterogeneous and homogenous free-radical polymerizations, and as an initiator in reversible addition-fragmentation chain transfer polymerization (RAFT).
4,4'-Azobis(4-cyanovaleric acid) is also used as a blowing agent for plastics and elastomers.

Uses of 4,4'-Azobis(4-Cyanovaleric Acid):
4,4'-Azobis(4-cyanovaleric acid) is used as a free radical imitator in polymer synthesis such as polyvinyl chloride, polyacrylonitrile, polyvinyl alcohol and synthetic fibers.
4,4'-Azobis(4-cyanovaleric acid) is utilized for both heterogeneous and homogenous free-radical polymerizations, and as an initiator in reversible addition-fragmentation chain transfer polymerization (RAFT).
4,4'-Azobis(4-cyanovaleric acid) is also used as a blowing agent for plastics and elastomers.

4,4'-Azobis(4-cyanovaleric acid) has been used in the preparation of polystyrene particles by polymerizing styrene in ethyl alcohol.
4,4'-Azobis(4-cyanovaleric acid) is a water soluble azo initiator usded in radical polymerization process of vinyls, acylamides, styrenes as well as other polymers.

4,4'-Azobis(4-cyanovaleric acid) is used as a free-radical initiator in polymerization reactions.
4,4'-Azobis(4-cyanovaleric acid) is used in the synthesis of functional polymers and copolymers.

4,4'-Azobis(4-cyanovaleric acid) is used in the preparation of polymer nanoparticles, microspheres, and latex systems.
4,4'-Azobis(4-cyanovaleric acid) is used as an azo initiator in aqueous and solution polymerization processes.

4,4'-Azobis(4-cyanovaleric acid) is used to produce polymers containing terminal carboxylic acid groups.
4,4'-Azobis(4-cyanovaleric acid) is used as a controlled radical source in oxidation and biochemical research.

Industry Uses:
Polymerization promoter

Advantages of 4,4'-Azobis(4-Cyanovaleric Acid):
4,4'-Azobis(4-cyanovaleric acid) provides efficient free-radical generation under controlled thermal conditions.
4,4'-Azobis(4-cyanovaleric acid) offers good suitability for aqueous and solution polymerization systems.

4,4'-Azobis(4-cyanovaleric acid) introduces carboxylic acid functionality that can support the preparation of functional polymers.
4,4'-Azobis(4-cyanovaleric acid) enables relatively predictable initiation behavior in polymer synthesis.

4,4'-Azobis(4-cyanovaleric acid) is useful in the preparation of polymer particles, copolymers, and surface-functionalized materials.
4,4'-Azobis(4-cyanovaleric acid) can also serve as a reproducible radical source in oxidation and biochemical research.

Biochem/physiol Actions of 4,4'-Azobis(4-Cyanovaleric Acid):
4,4'-Azobis(4-cyanovaleric acid) is an azo-initiator that induces lipid peroxidation of sunflower oil.

Stability and Reactivity of 4,4'-Azobis(4-Cyanovaleric Acid):

Chemical Stability:
Stable under recommended refrigerated storage conditions.
Thermal decomposition may occur when heated.

Reactivity:
Self-reactive azo compound that can decompose upon heating and generate free radicals.

Conditions to Avoid:
Heat, flames, sparks, ignition sources, electrostatic discharge and elevated temperatures.

Incompatible Materials:
Avoid contact with strong oxidizing agents and other incompatible reactive materials.

Hazardous Decomposition Products:
Thermal decomposition or combustion may produce carbon monoxide, carbon dioxide, nitrogen oxides and irritating fumes.

Handling and Storage of 4,4'-Azobis(4-Cyanovaleric Acid):

Safe Handling:
Handle in a well-ventilated area.
Avoid dust formation, inhalation and contact with skin or eyes.
Keep away from heat, sparks and open flames.

Storage Conditions:
Store tightly closed at 2–8°C in a dry, cool and well-ventilated place.
Keep away from heat, ignition sources and incompatible materials.

First Aid Measures of 4,4'-Azobis(4-Cyanovaleric Acid):

Inhalation:
Move the affected person to fresh air.
Obtain medical attention if symptoms develop.

Skin Contact:
Wash thoroughly with plenty of water and remove contaminated clothing.
Seek medical attention if irritation persists.

Eye Contact:
Rinse cautiously with plenty of water for at least 15 minutes.
Obtain medical attention.

Ingestion:
Rinse mouth with water.
Do not induce vomiting unless directed by medical personnel.
Seek medical advice if symptoms occur.

Firefighting Measures of 4,4'-Azobis(4-Cyanovaleric Acid):

Suitable Extinguishing Media:
Use water spray, dry chemical, foam or carbon dioxide as appropriate for the surrounding fire.

Specific Hazards:
Heating may cause self-accelerating decomposition and release irritating or toxic combustion products.

Protective Equipment:
Firefighters should wear self-contained breathing apparatus and suitable protective clothing.

Accidental Release Measures of 4,4'-Azobis(4-Cyanovaleric Acid):

Personal Precautions:
Remove ignition sources, ensure adequate ventilation and avoid generating or inhaling dust.
Wear appropriate protective equipment.

Environmental Precautions:
Prevent material from entering drains, surface water or soil.

Cleanup Methods:
Carefully collect spilled material using non-sparking tools and place it in a suitable closed container for disposal.

Exposure Controls/Personal Protective of 4,4'-Azobis(4-Cyanovaleric Acid):

Engineering Controls:
Provide adequate ventilation and minimize airborne dust.

Eye Protection:
Wear safety glasses or chemical safety goggles.

Hand Protection:
Wear suitable chemical-resistant protective gloves.

Skin Protection:
Wear appropriate protective clothing to minimize skin exposure.

Respiratory Protection:
Use suitable particulate respiratory protection when ventilation is inadequate or dust exposure may occur.

General Hygiene:
Wash hands thoroughly after handling and before eating, drinking or smoking.

Identifiers of 4,4'-Azobis(4-Cyanovaleric Acid):
CAS No.: 2638-94-0
Chemical Name: 4,4'-Azobis(4-cyanovaleric acid)
CBNumber: CB9344530
Molecular Formula: C12H16N4O4
Molecular Weight: 280.28
MDL Number: MFCD00002799

CAS Number: 2638-94-0
EC Number: 220-135-0
Molecular Formula: C12H16N4O4
Molecular Weight: 280.28 g/mol
PubChem CID: 92938
IUPAC Name: 4-[(4-carboxy-2-cyanobutan-2-yl)diazenyl]-4-cyanopentanoic acid
InChIKey: VFXXTYGQYWRHJP-UHFFFAOYSA-N
SMILES: CC(CCC(=O)O)(C#N)N=NC(C)(CCC(=O)O)C#N

Alternate Names: ABCVA; ACVA; 4,4′-Azobis(4-cyanopentanoic acid)
Application: 4,4'-Azobis(4-cyanovaleric acid) is an azo initiator used in radical polymerization processes
CAS Number: 2638-94-0
Purity: ≥97%
Molecular Weight: 280.28
Molecular Formula: C12H16N4O4

Molecular Weight: 280.28000
Exact Mass: 280.28
EC Number: 220-135-0
NSC Number: 114466
DSSTox ID: DTXSID3044629
HScode: 2927000090

Product Number: A1671
Purity / Analysis Method : >98.0%(T)
Molecular Formula / Molecular Weight: C__1__2H__1__6N__4O__4 = 280.28 
Physical State (20 deg.C): Solid
Storage Temperature : Refrigerated (0-10°C)
Condition to Avoid: Light Sensitive,Heat Sensitive
CAS RN: 2638-94-0
Reaxys Registry Number: 8273819
MDL Number: MFCD00002799

CAS Number: 2638-94-0
ChemSpider: 83896
ECHA InfoCard: 100.018.305
PubChem CID: 92938
CompTox Dashboard (EPA): DTXSID3044629
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+
Key: VFXXTYGQYWRHJP-FOCLMDBBSA-N
SMILES: CC(CCC(=O)O)(C#N)N=NC(C)(CCC(=O)O)C#N

CAS: 2638-94-0
IUPAC Name: (4S)-4-{2-[(1R)-3-carboxylato-1-cyano-1-methylpropyl]diazen-1-yl}-4-cyano-4-methylbutanoate
Molecular Formula: C12H14N4O4
InChI Key: VFXXTYGQYWRHJP-TXEJJXNPSA-L
SMILES: C[C@@](CCC([O-])=O)(N=N[C@](C)(CCC([O-])=O)C#N)C#N
Molecular Weight (g/mol): 278.27
Synonym: (4S)-4-{2-[(1R)-3-carboxylato-1-cyano-1-methylpropyl]diazen-1-yl}-4-cyano-4-methylbutanoate

Linear Formula: HOCOCH2CH2C(CH3)(CN)N=NC(CH3)(CN)CH2CH2COOH
CAS Number: 2638-94-0
Molecular Weight: 280.28
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 57646934
EC Number: 220-135-0
Beilstein/REAXYS Number: 1729856
MDL number: MFCD00002799
Assay: ≥98.0% (T)
Form: solid

Properties of 4,4'-Azobis(4-Cyanovaleric Acid):
Chemical formula: C12H16N4O4
Molar mass: 280.284 g·mol−1
Appearance: White crystalline powder
Melting point: 118 to 125 °C (244 to 257 °F; 391 to 398 K)
Solubility in water: Soluble

Melting point: 118-125 °C (dec.) (lit.)
Boiling point: 423°C (rough estimate)
Density: 1.2464 (rough estimate)
refractive index: 1.6081 (estimate)
storage temp.: 2-8°C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 3.98±0.10(Predicted)
color: White
Water Solubility: Soluble in water.
Sensitive: Light Sensitive
BRN: 1729856
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+
InChIKey: VFXXTYGQYWRHJP-FOCLMDBBSA-N
SMILES: CC(CCC(O)=O)(\N=N\C(C)(CCC(O)=O)C#N)C#N
LogP: 0.8 at 23℃

PSA: 146.90000
XLogP3: 1.73276
Appearance: white crystalline powder
Density: 1.23 g/cm3
Melting Point: 120-123 °C (decomp)
Boiling Point: 503.6ºC at 760 mmHg
Flash Point: 258.3±30.1 °C
Refractive Index: 1.546
Water Solubility: 
Soluble in water.
Storage Conditions: 2-8ºC
Vapor Pressure: 1.66E-11mmHg at 25°C

Quality Segment: 200
assay: ≥98.0% (T)
form: solid
impurities: ≤1% water
mp: 118-125 °C (dec.) (lit.)
functional group: azo, carboxylic acid, nitrile
storage temp.: 2-8°C
SMILES string: CC(CCC(O)=O)(\N=N\C(C)(CCC(O)=O)C#N)C#N
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+
InChI key: VFXXTYGQYWRHJP-FOCLMDBBSA-N

Molecular Weight: 280.28 g/mol
XLogP3-AA: 0.3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 8
Rotatable Bond Count: 8
Exact Mass: 280.11715500 Da
Monoisotopic Mass: 280.11715500 Da
Topological Polar Surface Area: 147 Ų
Heavy Atom Count: 20
Complexity: 466
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 2
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of 4,4'-Azobis(4-Cyanovaleric Acid):
Appearance: White to Almost white powder to crystal
Purity(Neutralization titration): min. 98.0%(after drying)
Drying loss: max. 20.0 %
NMR: confirm to structure

Appearance (Color): White to pale yellow
Form: Powder
Assay (unspecified): ≥97.5%
Loss on Drying: 15-20%

Names of 4,4'-Azobis(4-Cyanovaleric Acid):

Preferred IUPAC name:
4,4′-[(E)-Diazenediyl]bis(4-cyanopentanoic acid)

Other names:
4,4-Azobis(4-cyanovaleric acid)
4,4-Azobis(cyanovaleric acid)
4,4′-Azobis(4-cyanopentanoic acid)
ABCVA
ACVA