6046. Methyl Cyanoacrylate

Nomenclature

CAS number: 137-05-3
2-Cyano-2-propenoic acid methyl ester; 2-cyanoacrylic acid methyl ester; MCA; mecrilate; mecrylate; methyl 2-cyanoacrylate; methyl α-cyanoacrylate.
C5H5NO2; mol wt 111.10.
C 54.05%, H 4.54%, N 12.61%, O 28.80%.

Description and references

Reacts rapidly with water to form solid polymers. Preparative methods: A. E. Ardis, US 2467927 (1949 to B. F. Goodrich); C. H. McKeever, US 2912454 (1959 to Rohm & Haas). Prepn, polymerization and degradation: F. Leonard et al., J. Appl. Polym. Sci. 10, 259 (1966). Clinical evaluation for tubal occlusion in female sterilization: Contraception 31, 243 (1985). Review of chemistry and toxicology: R. Cary, Concise Int. Chem. Assess. Doc. No. 36 (WHO, Geneva, 2001) 33 pp.

Chemical structure

Properties

Clear, colorless liquid; strong, acrid odor; bp 48-49° (0.33-0.36 kPa). n20D 1.4459. nD25 1.443. d20 1.1044. Surface tension: 37.41 dynes/cm. Vapor pressure at 25°: <0.27 kPa. Sol or partially sol in methyl ethyl ketone, toluene, DMF, acetone, nitromethane.

Derivative

Polymer.

Nomenclature

CAS number: 25067-29-2
Poly(methyl 2-cyanoacrylate).

Caution

Potential symptoms of overexposure are irritation of eyes, skin, nose; blurred vision, lacrimation; rhinitis. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 204.

Use

In adhesives; in mfr of plastics, electronics, scientific instruments, jewelry, sports equip; in cable joining, manicuring, dentistry, mortuaries, fingerprint development.

Therapeutic Category

Tissue adhesive.

Keywords

Tissue Adhesive