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

4,4′-Azobis(4-cyanopentanoic acid) (ACPA) is a free radical initiator used in polymer synthesis.[1] ACPA is a water-soluble initiator used in both heterogeneous and homogeneous free-radical polymerizations. It is used as an initiator in reversible addition−fragmentation chain transfer polymerization (RAFT). When heated to decomposition, c. 70 °C, it releases N2 and produces 2 equivalents of reactive radicals capable of initiating polymerization.

4,4′-Azobis(4-cyanopentanoic acid)
Skeletal formula of ACPA
Ball-and-stick model of the ACPA molecule
Names
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
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.305
  • 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+ checkY
    Key: VFXXTYGQYWRHJP-FOCLMDBBSA-N checkY
  • CC(CCC(=O)O)(C#N)N=NC(C)(CCC(=O)O)C#N
Properties
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)
Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Sigma Aldrich Product Page


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