2-cyanoacrylic acid methyl ester

Structural formula
General
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
EC number	205-275-2
ECHA InfoCard	100,004,796
PubChem	8711
Wikidata	Q209367
properties
Molar mass	111.10 g · mol -1
Physical state	liquid
density	1.1 g cm −3
Melting point	−40 ° C
boiling point	47-49 ° C (2.4 hPa )
Vapor pressure	0.27 hPa (25 ° C)
solubility	almost insoluble in water (polymerized)
Refractive index	1.4430
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
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
MAK	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.

Manufacturing

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

use

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

Methyl cyanoacrylate and ethyl cyanoacrylate , WHO (PDF; 179 kB)

Individual evidence

↑ ^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) .
↑ ^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.
↑ 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.
↑ 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 .
↑ Safety data sheet Cyanolit 402. (PDF; 81 kB) panacol, October 5, 2009, accessed on August 12, 2011 .
↑ www.reciprocalnet.org .

[GESTIS-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) .

[ICSC-2] International Chemical Safety Card (ICSC) for Methyl-2-cyanoacrylate at the National Institute for Occupational Safety and Health (NIOSH), accessed on December 26, 2017.

[CRC90_3_346-3] 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.

[CLP_100.004.796-4] 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 .

[sdb-5] Safety data sheet Cyanolit 402. (PDF; 81 kB) panacol, October 5, 2009, accessed on August 12, 2011 .

[6] www.reciprocalnet.org .