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 ;
3D model (JSmol)	Interactive image;
ChemSpider	21678 ;
ECHA InfoCard	100.027.045
PubChem CID	23167;
UNII	6C655P1XVG ;
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 Key: RPQUGMLCZLGZTG-UHFFFAOYSA-N ; 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).
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	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, 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.

References

Singer, A. J.; McClain, S. A.; Katz, A. (2004). "A porcine epistaxis model: hemostatic effects of octylcyanoacrylate". Otolaryngology–Head and Neck Surgery. 130 (5): 553–557. doi:10.1016/j.otohns.2003.09.035. PMID 15138419.

Octyl cyanoacrylate

References

See also