Methyl cyanoacrylate

Methyl cyanoacrylate (MCA; also sometimes referred to as α-cyanoacrylate or alpha-cyanoacrylate)^[3] is an organic compound that contains several functional groups: a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues.^[4][5] It can be encountered under many trade names. Methyl cyanoacrylate is less commonly encountered than ethyl cyanoacrylate.

Methyl cyanoacrylate

Names
Preferred IUPAC name Methyl 2-cyanoprop-2-enoate
Other names Methyl 2-cyanopropenoate Methyl 2-cyanoacrylate 2-Cyano-2-propenoic acid methyl ester MCA Methyl alpha-cyanoacrylate Mecrylate Ad/here Adhere CA 7 Cemedine 3000 Coapt Cyanobond 5000 Eastman 910 Fimofix P 1048 Mecrilat Mecrilate Sicomet 7000 Three Bond 1701[1]
Identifiers
CAS Number	137-05-3 Y
3D model (JSmol)	Interactive image
ChemSpider	8387 Y
ECHA InfoCard	100.004.796
PubChem CID	8711
UNII	WN7979561R Y
CompTox Dashboard (EPA)	DTXSID4025589
InChI InChI=1S/C5H5NO2/c1-4(3-6)5(7)8-2/h1H2,2H3 Y Key: MWCLLHOVUTZFKS-UHFFFAOYSA-N Y InChI=1/C5H5NO2/c1-4(3-6)5(7)8-2/h1H2,2H3 Key: MWCLLHOVUTZFKS-UHFFFAOYAW
SMILES C=C(C(OC)=O)C#N
Properties
Chemical formula	C5H5NO2
Molar mass	111.100 g·mol−1
Density	1.1
Melting point	−40 °C (−40 °F; 233 K)
Boiling point	48 to 49 °C (118 to 120 °F; 321 to 322 K) (2.5–2.7 mmHg)
Solubility in water	30% (20 °C)[2]
Vapor pressure	0.2 mmHg (25 °C)[2]
Hazards
Flash point	79 °C; 174 °F; 352 K[2]
NIOSH (US health exposure limits):
PEL (Permissible)	None[2]
REL (Recommended)	TWA 2 ppm (8 mg/m3) ST 4 ppm (16 mg/m3)[2]
IDLH (Immediate danger)	N.D.[2]
Related compounds
Related Cyanoacrylates	Ethyl cyanoacrylate Butyl cyanoacrylate Octyl cyanoacrylate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

It is soluble in acetone, methyl ethyl ketone, nitromethane, and dichloromethane.^[6] MCA polymerizes rapidly in presence of moisture.

Safety

Heating the polymer causes depolymerization of the cured MCA, producing gaseous products which are a strong irritant to the lungs and eyes. With regard to occupational exposure to MCA, the National Institute for Occupational Safety and Health recommends workers do not exceed exposures over 2 ppm (8 mg/m³) over an eight-hour workshift, or over 4 ppm (16 mg/m³) over a short-term exposure.^[7]