Ethyl 2-cyanoacrylate

January 20, 2020
I can glue almost anything.
What molecule am I?
Image of Ethyl 2-cyanoacrylate 3D Image of Ethyl 2-cyanoacrylate

Ethyl 2-cyanoacrylate is a liquid that you’ve probably used around the house. Because of its conjugated unsaturated groups, it polymerizes easily. It is prepared by condensing ethyl 2-cyanoacetate with formaldehyde, followed by thermal decomposition of the resulting polymer.

Ethyl 2-cyanoacrylate and other less common 2-cyanoacrylate esters are the active ingredients in commercial superglues or instant glues. Some of these products contain additives such as fumed silica to make them more viscous or rubber to make them more impact resistant.

Cyanoacrylates were discovered serendipitously during World War II when scientists at B.F. Goodrich (located in Akron, OH at the time) sought suitable clear plastics for gun sights. Chemist Harry Coover Jr. and co-workers found that the esters auto-polymerized and stuck to everything in sight. Because of the wartime urgency for other materials, cyanoacrylates were abandoned until 1951, when Coover, then at Eastman Chemical (Eastport, TN), and colleague Fred Joyner “rediscovered” it. The first commercial glue appeared in 1958.

Ethyl 2-cyanoacrylate and its cousins polymerize instantly in water. The small amount of moisture in air is enough to initiate polymerization. The polymer forms within a matter of minutes, creating a bond that is often stronger than the materials it joins.

Despite its strength, the polymer can be removed by soaking it in acetone or mild acids. Household products such as nail polish remover or lemon juice will do the trick. 

Ethyl 2-cyanoacrylate hazard information

Hazard class* Hazard statement
Flammable liquids, category 4 H227—Combustible liquid
Skin corrosion/irritation, category 2 H315—Causes skin irritation Chemical Safety Warning
Serious eye damage/eye irritation, category 2A H319—Causes serious eye irritation  Chemical Safety Warning
Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 H335—May cause respiratory irritation Chemical Safety Warning

*Globally Harmonized System of Classification and Labeling of Chemicals.
Explanation of pictograms.

Ethyl 2-cyanoacrylate 
fast facts

CAS Reg. No. 7085-85-0
2-Propenoic acid, 2-cyano-, ethyl ester
Empirical formula C6H7NO2
Molar mass 125.13 g/mol
Appearance Colorless liquid
Boiling point 54–56 ºC @ 3 torr
Water solubility Polymerizes 

MOTW update:
April 5, 2021

Ethyl 2-cyanoacrylate (ECA) is the primary active ingredient in most superglues. Recently, a new joint venture between Arkema (Colombes, France) and Cartell Chemical (Minxiong Township, Taiwan) was formed to develop other cyanoacrylate esters that may be useful as engineering adhesives. The first step is to build a plant to make 2-methoxyethyl 2-cyanoacrylate, a derivative that avoids ECA’s deficiencies for industrial use.

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