Methyl cyanoacrylate

Methyl cyanoacrylate
Structural formula of methyl cyanoacrylate
Ball-and-stick model of the methyl cyanoacrylate molecule
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.796 Edit this at Wikidata
UNII
  • InChI=1S/C5H5NO2/c1-4(3-6)5(7)8-2/h1H2,2H3 checkY
    Key: MWCLLHOVUTZFKS-UHFFFAOYSA-N checkY
  • InChI=1/C5H5NO2/c1-4(3-6)5(7)8-2/h1H2,2H3
    Key: MWCLLHOVUTZFKS-UHFFFAOYAW
  • C=C(C(OC)=O)C#N
Properties
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)
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
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 checkY☒N ?)

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.

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]

References

  1. ^ Methyl 2-cyanoacrylate at Cameo Chemicals
  2. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0405". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ "Cyanoacrylate Derivative - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2021-11-09.
  4. ^ Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut; Shaffer, Timothy D.; Nandi, Partha (2020). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4. ISBN 9783527303854.
  5. ^ Methyl 2-cyanoacrylate at Inchem.org
  6. ^ Palm Labs Adhesives Archived 2008-12-08 at the Wayback Machine
  7. ^ CDC - NIOSH Pocket Guide to Chemical Hazards