2-cyanoacrylic acid methyl ester

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Structural formula
Structural formula of 2-cyanoacrylic acid methyl ester
Surname 2-cyanoacrylic acid methyl ester
other names
  • Methyl cyanoacrylate
  • MCA
  • 2-cyano-2-propenoic acid methyl ester
Molecular formula C 5 H 5 NO 2
Brief description

yellowish liquid with a pungent odor

External identifiers / databases
CAS number 137-05-3
EC number 205-275-2
ECHA InfoCard 100,004,796
PubChem 8711
Wikidata Q209367
Molar mass 111.10 g · mol -1
Physical state



1.1 g cm −3

Melting point

−40 ° C

boiling point

47-49 ° C (2.4 hPa )

Vapor pressure

0.27 hPa (25 ° C)


almost insoluble in water (polymerized)

Refractive index


safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning


H and P phrases H: 319-335-315
P: 261-264-271-280-302 + 352-304 + 340-305 + 351 + 338-312-321-332 + 313-337 + 313-362-403 + 233-405

9.2 mg m −3

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2-Cyanoacrylic acid methyl ester , also called methyl cyanoacrylate , is a nitrile derivative of the methyl ester of acrylic acid . It belongs to the group of acrylates , more precisely cyanoacrylates .

Chemical properties

2-Cyanoacrylic acid methyl ester is a colorless liquid with a characteristic odor, which polymerizes very quickly on contact with moisture . It is the simplest 2-cyanoacrylic acid ester, which also includes 2-cyanoacrylic acid ethyl ester , 2-cyanoacrylic acid butyl ester and others.


2-Cyanoacrylic acid methyl ester can be produced by reacting cyanoacetic acid methyl ester with formaldehyde in a condensation reaction


2-Cyanacrylsäuremethylester is mainly used as superglue used and cured most often in less than a minute. In addition to household use, it is also used in medicine for sutures without thread. It is in vapor form in the forensics used fingerprints to make them visible. The compound was first investigated by researchers from Eastman Kodak in the 1930s / 1940s and patented in 1956.

Web links

Individual evidence

  1. a b c d e f Entry on methyl 2-cyanoacrylate in the GESTIS substance database of the IFA , accessed on February 21, 2017(JavaScript required) .
  2. a b International Chemical Safety Card (ICSC) for Methyl-2-cyanoacrylate at the National Institute for Occupational Safety and Health (NIOSH), accessed on December 26, 2017.
  3. David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-346.
  4. Entry on Mecrilate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. Safety data sheet Cyanolit 402. (PDF; 81 kB) panacol, October 5, 2009, accessed on August 12, 2011 .
  6. www.reciprocalnet.org .