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

Base Information

• Chemical Name: 4,4'-Azobis(4-cyanovaleric acid)
• CAS No.: 2638-94-0
• Deprecated CAS: 158947-06-9,159172-39-1,209196-69-0,25532-89-2,30248-30-7,252237-53-9,306284-14-0,159172-39-1,209196-69-0,252237-53-9,30248-30-7,306284-14-0
• Molecular Formula: C12H16N4O4
• Molecular Weight: 280.283
• Hs Code.: 29270000
• European Community (EC) Number: 220-135-0
• NSC Number: 114466
• DSSTox Substance ID: DTXSID3044629,DTXSID00859752
• Nikkaji Number: J80.531I
• Wikipedia: 4,4%27-Azobis(4-cyanopentanoic_acid),4'-Azobis(4-cyanopentanoic_acid)
• Wikidata: Q4637047
• ChEMBL ID: CHEMBL3185815
• Mol file: 2638-94-0.mol

Synonyms:4,4'-azo-bis(4-CNVA);4,4'-azobis(4-cyanovaleric acid)

Chemical Property of 4,4'-Azobis(4-cyanovaleric acid)

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 118-125 °C (dec.)(lit.)
• Refractive Index: 1.6081 (estimate)
• Boiling Point: 503.6 °C at 760 mmHg
• PKA: 3.98±0.10(Predicted)
• Flash Point: 258.3 °C
• PSA: 146.90000
• Density: 1.23 g/cm³
• LogP: 1.73276
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Water Solubility.: Soluble in water.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 280.11715500
• Heavy Atom Count: 20
• Complexity: 466

Purity/Quality:

99% ^*data from raw suppliers

4,4′-Azobis(4-cyanovaleric acid) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 15-16-22-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: CC(CCC(=O)O)(C#N)N=NC(C)(CCC(=O)O)C#N
• Uses: 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 imitator in polymer synthesis such as polyvinyl chloride, polyacrylonitrile, polyvinyl alcohol and synthetic fibers. It is utilized for both heterogeneous and homogenous free-radical polymerizations, and as an initiator in reversible addition-fragmentation chain transfer polymerization (RAFT). It 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.

Technology Process of 4,4'-Azobis(4-cyanovaleric acid)

There total 3 articles about 4,4'-Azobis(4-cyanovaleric acid) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 26.0%

4,4'-hydrazo-bis-4-cyano-pentanoic acid → 4,4'-dicyano-4,4'-azo-di-valeric acid (2638-94-0,30248-30-7)

Guidance literature:

With oxone; potassium bromide; In water; at 20 ℃;

DOI:10.1081/SCC-120014980

Reference yield:

sodium cyanide (143-33-9,25596-52-5) + levulinic acid (123-76-2) → 4,4'-dicyano-4,4'-azo-di-valeric acid (2638-94-0,30248-30-7)

Guidance literature:

With sulfuric acid; water; hydrazine; optically inactive stereoisomer(ic) of mp: 111 degree; Behandeln des Reaktionsgemisches mit Brom;

DOI:10.1039/jr9550004256

Reference yield:

→ 4,4'-dicyano-4,4'-azo-di-valeric acid (2638-94-0,30248-30-7)

Guidance literature:

DOI:10.1002/macp.1960.020360102

upstream raw materials:

sodium cyanide

levulinic acid

Downstream raw materials:

C₁₂H₁₀Br₃N₂O₃

4-cyano-4-(thiobenzoylthio)pentanoic acid

4-cyano-4-(phenylcarbonothioylthio)pentanoic acid N-succinimidyl ester

4-cyanopentanoic acid diselenobenzoate

Refernces

• 1、 Tamhankar,Desai, Uday V.,Mane,Kulkarni,Wadgaonkar. "Oxidation of alkylcyanohydrazines to azo-bis nitriles using Oxone-potassium bromide in aqueous medium". . p. 3643 - 3646. Retrieved 2007/10/03.