Methyl vinyl ether
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Preferred IUPAC name
Methoxyethene
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| Other names
Ethenyl methyl ether
Vinyl methyl ether |
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| Identifiers | |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.003.161 |
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PubChem CID
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| UNII | |
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| Properties | |
| C3H6O | |
| Molar mass | 58.08 g·mol−1 |
| Density | 0.77 g/cm−3 |
| Melting point | −122 °C (−188 °F; 151 K) |
| Boiling point | 6 °C (43 °F; 279 K) |
| Vapor pressure | 157 kPa (20 °C) |
| Hazards | |
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EU classification (DSD) (outdated)
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 F+ |
| R-phrases (outdated) | R12 |
| S-phrases (outdated) | (S2), S9, S16, S33 |
| Flash point | −60 °C (−76 °F; 213 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Methyl vinyl ether is an organic compound with the chemical formula C3H6O. It is the simplest chemical that contains both an alkene group and an alkyl group with an ether linkage. The compound can be made by reaction of acetylene and methanol in presence of a base.
The alkene portion of the molecule is reactive in many ways. It is prone to polymerization, leading to formation of poly(methyl vinyl ether) (PMVE, CAS: 9003-09-2). This mode of reactivity is analogous to the way vinyl acetate and vinyl chloride can be polymerized to form polyvinyl acetate and polyvinyl chloride, respectively. The alkene can also react in [4+2] cycloaddition reactions. The reaction of it with acrolein is the first step in the commercial synthesis of glutaraldehyde.
The compound is useful as a synthon for nucleophilic acylation, via deprotonation of the alkene adjacent to the oxygen attachment. In particular, this approach allows synthesis of a variety of acyl derivatives of silicon, germanium, and tin that cannot be made easily by other routes.
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