Methyl cyanoacrylate
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| Names | |
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| 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)
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| ChemSpider | |
| ECHA InfoCard | 100.004.796 |
PubChemCID
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| UNII | |
CompTox Dashboard(EPA)
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| Properties | |
| C5H5NO2 | |
| Molar mass | 111.100g·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) (2.5–2.7mmHg) |
| 30% (20°C)[2] | |
| Vapor pressure | 0.2mmHg (25°C)[2] |
| Hazards | |
| Flash point | 79 °C; 174 °F; 352 K[2] |
| NIOSH(US health exposure limits): | |
PEL(Permissible)
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None[2] |
REL(Recommended)
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TWA 2 ppm (8mg/m3) ST 4 ppm (16mg/m3)[2] |
IDLH(Immediate danger)
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N.D.[2] |
| Related compounds | |
Related
Cyanoacrylates |
Ethyl cyanoacrylate Butyl cyanoacrylate Octyl cyanoacrylate |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Methyl cyanoacrylate(MCA;also sometimes referred to asα-cyanoacrylateoralpha-cyanoacrylate)[3]is anorganic compoundthat contains severalfunctional groups:amethylester,anitrile,and analkene.It is a colorless liquid with lowviscosity.Its chief use is as the main component ofcyanoacrylate glues.[4][5]It can be encountered under manytrade names.Methyl cyanoacrylate is less commonly encountered thanethyl cyanoacrylate.
It is soluble inacetone,methyl ethyl ketone,nitromethane,anddichloromethane.[6]MCApolymerizesrapidly in presence ofmoisture.
Safety
[edit]Heating the polymer causesdepolymerizationof the cured MCA, producing gaseous products which are a strong irritant to thelungsandeyes. With regard tooccupational exposureto MCA, theNational Institute for Occupational Safety and Healthrecommends 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
[edit]- ^Methyl 2-cyanoacrylateat Cameo Chemicals
- ^abcdefNIOSH Pocket Guide to Chemical Hazards."#0405".National Institute for Occupational Safety and Health(NIOSH).
- ^"Cyanoacrylate Derivative - an overview | ScienceDirect Topics".www.sciencedirect.com.Retrieved2021-11-09.
- ^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.ISBN9783527303854.
- ^Methyl 2-cyanoacrylateat Inchem.org
- ^Palm Labs AdhesivesArchived2008-12-08 at theWayback Machine
- ^CDC - NIOSH Pocket Guide to Chemical Hazards