Octyl cyanoacrylate

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 (Jmol)	Interactive image
ChemSpider	21678 Y
ECHA InfoCard	100.027.045
PubChem CID	23167
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	209.29 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  (what is YN ?)
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.

In medical and veterinary applications, octyl cyanoacrylate, n-butyl cyanoacrylate and isobutyl cyanoacrylate are commonly used. They provide rapid wound closure, 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 octyl cyanoacrylate and n-butyl cyanoacrylate 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 lungs and eyes.