Octyl cyanoacrylate

Not to be confused with 2-Octyl cyanoacrylate.

Octyl cyanoacrylate
IUPAC name Octyl 2-cyanopropenoate
Other names Ocrylate; Octyl 2-cyanoacrylate
Identifiers
CAS number	6701-17-3
PubChem	23167
Jmol-3D images	Image 1
SMILES N#CC(C(OCCCCCCCC)=O)=C
InChI InChI=InChI=1S/C12H19NO2/c1-3-4-5-6-7-8-9-15-12(14)11(2)10-13/h2-9H2,1H3
Properties
Molecular formula	C12H19NO2
Molar mass	209.28 g mol−1
Appearance	Colorless liquid
Solubility in water	Reacts
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Octyl cyanoacrylate (OCA), a cyanoacrylate ester, is an octyl ester of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. Its chief use is as the main component of medical cyanoacrylate glues. It can be encountered under various trade names including GluStitch, derma+flex® QS™, SurgiSeal, FloraSeal, Octylseal, Dermabond, Nexaband, and others.

In medical and veterinary applications, the related compounds n-butyl cyanoacrylate and isobutyl cyanoacrylate are commonly used. They are bacteriostatic and their use is usually painless. Butyl esters provide a stronger bond, but the glue is rigid. The octyl ester, while providing weaker bond, is more flexible.

It polymerizes rapidly in presence of moisture.

Heating to higher temperatures causes pyrolysis and depolymerization of the cured glue, producing gaseous products strongly irritating to lungs and eyes.

See also

• Methyl cyanoacrylate
• Ethyl cyanoacrylate
• Butyl cyanoacrylate
• 2-Octyl cyanoacrylate