Butyl cyanoacrylate
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Preferred IUPAC name
Butyl 2-cyanoprop-2-enoate
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| Other names
Butyl 2-cyanopropenoate
Butyl 2-cyanoacrylate 2-Cyano-2-propenoic acid n-butyl ester n-Butyl 2-cyanoacrylate n-BCA NBCA n-Butyl alpha-cyanoacrylate Enbucrilate (INN) |
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3D model (Jmol)
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| ChemSpider | |
| ECHA InfoCard | 100.026.866 |
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| Properties | |
| C8H11NO2 | |
| Molar mass | 153.18 g·mol−1 |
| Density | 1.4430 |
| Boiling point | 83 to 84 °C (181 to 183 °F; 356 to 357 K) at 3 mmHg |
| Hazards | |
| Flash point | > 80 °C (176 °F; 353 K) |
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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 | |
n-Butyl cyanoacrylate (n-BCA, NBCA), a cyanoacrylate ester, is a butyl ester of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. It is insoluble in water. Its chief use is as the main component of medical cyanoacrylate glues. It can be encountered under various trade names, e.g. MediBond, MediCryl, PeriAcryl, GluStitch, Xoin, Gesika, VetGlu, Vetbond, LiquiVet, Indermil, LiquiBand, Histoacryl, IFABond and others. The generic international nonproprietary name (INN) for NBCA is embucrilate.
In medical and veterinary applications, NBCA, isobutyl cyanoacrylate, and octyl cyanoacrylate are commonly used. They are bacteriostatic and their use is usually painless. Butyl esters provide stronger bond, but are rigid. Octyl esters, while providing weaker bond, are more flexible. Blends of octyl cyanoacrylate and n-butyl cyanoacrylate are available (such as GLUture) which offer both flexibility and a strong bond. n-Butyl cyanoacrylate is also used for embolization of cerebral arteriovenous malformations before their surgical treatment.
NBCA is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride.
NBCA in monomer form polymerizes rapidly in presence of ionic substances such as moisture, blood, or tissue fluids.
NBCA has unique properties compared to other cyanoacrylates such as octyl cyanoacrylate or isoamyl cyanoacrylate. The polymerized form has excellent tensile strength and is very effective in closing surgical or wound incisions.
The closure of the wound or cut is quick (about 30 to 45 seconds) and the product has inherently some valuable bacteriostatic properties. The cosmetic outcome of the closure is comparable or generally better than an equivalent suture substitute with least amount of scarring visible after three to six months.
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Wikipedia