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  • 11590 - 4,4′-Azobis(4-cyanovaleric acid)

11590 Sigma-Aldrich

4,4′-Azobis(4-cyanovaleric acid)

≥98.0% (T)

Synonym: 4,4′-Azobis(4-cyanopentanoic acid), ABCVA, ACVA

  • CAS Number 2638-94-0

  • Linear Formula HOCOCH2CH2C(CH3)(CN)N=NC(CH3)(CN)CH2CH2COOH

  • Molecular Weight 280.28

  •  Beilstein/REAXYS Number 1729856

  •  EC Number 220-135-0

  •  MDL number MFCD00002799

  •  PubChem Substance ID 57646934

  •  NACRES NA.22



Related Categories Azo Compounds, Azo/Diazo Compounds, Building Blocks, Chemical Synthesis, Free Radical Initiators,
Quality Level   200
assay   ≥98.0% (T)
impurities   ≤1% water
mp   118-125 °C (dec.) (lit.)
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+



4,4′-Azobis(4-cyanovaleric acid) has been used in the preparation of polystyrene particles by polymerizing styrene in ethyl alcohol.

Biochem/physiol Actions

4,4′-azobis(4-cyanovaleric acid) is an azo-initiator that induces lipid peroxidation of sunflower oil.

Safety & Documentation

Safety Information

GHS02  GHS02
Signal word 
Hazard statements 
UN3226 - class 4.1 - Self-reactive solid type D (4,4'-AZOBIS(4-CYANOVALERIC ACID))
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Protocols & Articles


A micro review of reversible addition/fragmentation chain transfer (RAFT) polymerization

Reversible addition/fragmentation chain transfer (RAFT) polymerization is a reversible deactivation radical polymerization (RDRP) and one of the more versatile methods for providing living characteri...
Keywords: Biomaterials, Living polymerization, Nanotechnology, Polymerization reactions, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations, transformation

Applying ARGET ATRP to the Growth of Polymer Brush Thin Films by Surface-initiated Polymerization

In 2006, Matyjaszewski and co-workers first described controlled radical polymerization by Activators ReGenerated by Electron Transfer Atom Transfer Radical Polymerization (ARGET ATRP),1-3 a developm...
Keywords: Antimicrobials, Ligands, Nanotubes, Oxidations, Polymerization reactions, Radical polymerization, Reductions, Reversible addition-fragmentation chain transfer polymerizations, Solution polymerization, Solvents

Concepts and Tools for RAFT Polymerization

Reversible addition/fragmentation chain transfer (RAFT) is a form of living radical polymerization. RAFT polymerization was discovered at CSIRO in 1998.1 It soon became the focus of intensive researc...
Keywords: Polymerization reactions, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations

Copper(I)-mediated Living Radical Polymerization in the Presence of Pyridylmethanimine Ligands

Emergence of living radical polymerization mediated by transition metal catalysts in 1995 was a seminal piece of work in the field of synthetic polymer chemistry.1-3 Since this date, many transition ...
Keywords: Catalysis, Condensations, Evaporation, Filtration, Ligands, Oxidations, Polymer science, Polymerization reactions, Precipitation, Purification, Radical polymerization, Reductions, Solvents

Initiator/Stabilizer FAQs

In a free-radical addition polymerization, the choice of polymerization initiator depends mainly on two factors: a) its solubility and b) its decomposition temperature. If the polymerization is perfo...
Dr. S. S. Newaz
Material Matters 2006, 1.1, 3.
Keywords: Bacterial conjugations, Chromatography, Column chromatography, Emulsion polymerization, Polymerization reactions, Precipitation, Radical polymerization

Tools for Performing ATRP (Atom Transfer Radical Polymerization)

Controlled radical polymerization (CRP) techniques have been reviewed in a number of articles1,2 and books,3 and include nitroxide-mediated polymerization (NMP),4-7 reversible addition fragmentation ...
Sebastian Grajales
Keywords: Ligands, Polymerization reactions, Purification, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations, Solution polymerization

Typical Procedures for Polymerizing via ATRP

The following two procedures describe two ATRP polymerization reactions as performed by Prof. Dave Hadddleton′s research group at the University of Warwick.
Keywords: Gas chromatography, Ligands, Nuclear magnetic resonance spectroscopy, Polymerization reactions, Size-exclusion chromatography, Solvents

Typical Procedures for Polymerizing via RAFT

RAFT (Reversible Addition/Fragmentation Chain Transfer) is a form of living radical polymerization involving conventional free radical polymerization of a substituted monomer in the presence of a sui...
Keywords: Nuclear magnetic resonance spectroscopy, Polymerization reactions, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations

Peer-Reviewed Papers


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