Octyl cyanoacrylate

{{distinguish|2-Octyl cyanoacrylate}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 486597500

| ImageFile = Octyl-cyanoacrylate-2D-skeletal.svg

| ImageSize = 200px

| ImageName = Skeletal formula

| ImageFile1 = Octyl cyanoacrylate 3D spacefill.png

| ImageSize1 = 220px

| ImageAlt1 = Space-filling model of the octyl cyanoacrylate molecule

| PIN = Octyl 2-cyanoprop-2-enoate

| OtherNames = Octyl 2-cyanopropenoate
Octyl 2-cyanoacrylate
Ocrylate

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 6701-17-3

| EINECS =

| PubChem = 23167

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6C655P1XVG

| SMILES = N#CC(C(OCCCCCCCC)=O)=C

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 21678

| InChI = 1/C12H19NO2/c1-3-4-5-6-7-8-9-15-12(14)11(2)10-13/h2-9H2,1H3

| InChIKey = RPQUGMLCZLGZTG-UHFFFAOYAE

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C12H19NO2/c1-3-4-5-6-7-8-9-15-12(14)11(2)10-13/h2-9H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = RPQUGMLCZLGZTG-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| Appearance = Colorless liquid

| C=12|H=19|N=1|O=2

| MeltingPt =

| BoilingPt = 297.6±23.0 °C

| Density = 1.0±0.1 g/cm3

| Solubility = Reacts

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| Section3 = {{Chembox Hazards

| FlashPt = 137.2±9.4 °C

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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,{{Cite journal |last=Singer |first=A. J. |last2=McClain |first2=S. A. |last3=Katz |first3=A. |title=A porcine epistaxis model: hemostatic effects of octylcyanoacrylate |journal=Otolaryngology–Head and Neck Surgery |year=2004 |volume=130 |pmid=15138419 |issue=5 |pages=553–557 |doi=10.1016/j.otohns.2003.09.035 }} are bacteriostatic, and their use is usually painless.{{Citation needed|date = July 2015}} 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.