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| 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 | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.004.796 
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| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C5H5NO2 |
| Molar mass | 111.100 g·mol |
| 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) |
| Vapor pressure | 0.2 mmHg (25 °C) |
| Hazards | |
| Flash point | 79 °C; 174 °F; 352 K |
| NIOSH (US health exposure limits): | |
| PEL (Permissible) | None |
| REL (Recommended) | TWA 2 ppm (8 mg/m) ST 4 ppm (16 mg/m) |
| IDLH (Immediate danger) | N.D. |
| 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 , 100 kPa).
 N verify (what is ?)
Infobox references
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Methyl cyanoacrylate (MCA; also sometimes referred to as α-cyanoacrylate or alpha-cyanoacrylate) 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. 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. 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/m) over an eight-hour workshift, or over 4 ppm (16 mg/m) over a short-term exposure.
References
- Methyl 2-cyanoacrylate at Cameo Chemicals
- ^ NIOSH Pocket Guide to Chemical Hazards. "#0405". National Institute for Occupational Safety and Health (NIOSH).
- "Cyanoacrylate Derivative - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2021-11-09.
- 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.
- Methyl 2-cyanoacrylate at Inchem.org
- Palm Labs Adhesives Archived 2008-12-08 at the Wayback Machine
- CDC - NIOSH Pocket Guide to Chemical Hazards