Methyl vinyl ether

Methyl vinyl ether is an organic compound with the chemical formula CH₃OCH=CH₂. A colorless gas, it is the simplest enol ether. It is used as a synthetic building block, as is the related compound ethyl vinyl ether (a liquid at room temperature).

Methyl vinyl ether

Names
Preferred IUPAC name Methoxyethene
Other names Ethenyl methyl ether Vinyl methyl ether
Identifiers
CAS Number	107-25-5 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	7573 Y
ECHA InfoCard	100.003.161
EC Number	203-475-4
PubChem CID	7861
UNII	G2OHX46576 N
UN number	1087
CompTox Dashboard (EPA)	DTXSID4026761
InChI InChI=1S/C3H6O/c1-3-4-2/h3H,1H2,2H3 Y Key: XJRBAMWJDBPFIM-UHFFFAOYSA-N Y
SMILES O(C=C)C COC=C
Properties
Chemical formula	C3H6O
Molar mass	58.080 g·mol−1
Density	0.77 g/cm−3[1]
Melting point	−122 °C (−188 °F; 151 K)[1]
Boiling point	6 °C (43 °F; 279 K)[1]
Vapor pressure	157 kPa (20 °C)[1]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H220
Precautionary statements	P210, P377, P381, P403
NFPA 704 (fire diamond)	2 4 2 W
Flash point	−60 °C (−76 °F; 213 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Preparation

Methyl vinyl ether can be made by reaction of acetylene and methanol in presence of a base.^[2][3]

Reactions

The alkene portion of the molecule is reactive in many ways. It is prone to polymerization, leading to formation of polyvinyl ethers. Polymerization is typically initiated with Lewis acids such as boron trifluoride.^[4] 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.

Methyl vinyl ether also participates in [4+2] cycloaddition reactions.^[5] Its reaction with acrolein is the first step in the commercial synthesis of glutaraldehyde.

The alkene can be deprotonated at the vinyl carbon adjacent to the oxygen.^[6] In particular, this approach allows the synthesis of a variety of acyl derivatives of silicon, germanium, and tin that cannot be made easily by other routes.^[7][8][9]

Toxicity

The toxicity of vinyl ethers has been heavily investigated because divinyl ether has been used as an anesthetic. The acute LD50 for methyl vinyl ether is greater than 4 g/kg (rats, oral).^[3]