Octyl cyanoacrylate

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.

Octyl cyanoacrylate

Names
Preferred IUPAC name Octyl 2-cyanoprop-2-enoate
Other names Octyl 2-cyanopropenoate Octyl 2-cyanoacrylate Ocrylate
Identifiers
CAS Number	6701-17-3 N
3D model (JSmol)	Interactive image
ChemSpider	21678 Y
ECHA InfoCard	100.027.045
PubChem CID	23167
UNII	6C655P1XVG Y
CompTox Dashboard (EPA)	DTXSID10217208
InChI InChI=1S/C12H19NO2/c1-3-4-5-6-7-8-9-15-12(14)11(2)10-13/h2-9H2,1H3 Y Key: RPQUGMLCZLGZTG-UHFFFAOYSA-N Y InChI=1/C12H19NO2/c1-3-4-5-6-7-8-9-15-12(14)11(2)10-13/h2-9H2,1H3 Key: RPQUGMLCZLGZTG-UHFFFAOYAE
SMILES N#CC(C(OCCCCCCCC)=O)=C
Properties
Chemical formula	C12H19NO2
Molar mass	209.289 g·mol−1
Appearance	Colorless liquid
Solubility in water	Reacts
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

In medical and veterinary applications, OCA, n-butyl cyanoacrylate (n-BCA) and isobutyl cyanoacrylate (ICA) are commonly used. They provide rapid wound closure,[1] 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. Blends of OCA and n-BCA are available which offer both flexibility and a strong bond.

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 the lungs and eyes.