Harman Patil (Editor)

Methyl vinyl ether

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Formula
  
C3H6O

Boiling point
  
6 °C

Density
  
770 kg/m³

Melting point
  
122 °C

Methyl vinyl ether Curved Arrow Press Forum methyl vinyl ether resonance structures

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.

Methyl vinyl ether FileMethylvinyletherpng Wikimedia Commons

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.

Methyl vinyl ether wwwsigmaaldrichcomcontentdamsigmaaldrichstr

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.

Methyl vinyl ether Methyl vinyl ether 98 SigmaAldrich
Methyl vinyl ether organic chemistry Draw a simplified MO diagram for the pi system

Methyl vinyl ether Polymethyl vinyl etheraltmaleic acid average Mw 216000 by LS

Methyl vinyl ether substancetooltipashxid3672

References

Methyl vinyl ether Wikipedia