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Methyl vinyl ether

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Methyl vinyl ether
Names
Preferred IUPAC name Methoxyethene
Other names Ethenyl methyl ether
Vinyl methyl ether
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.161 Edit this at Wikidata
EC Number
  • 203-475-4
PubChem CID
UNII
UN number 1087
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H6O/c1-3-4-2/h3H,1H2,2H3Key: XJRBAMWJDBPFIM-UHFFFAOYSA-N
SMILES
  • O(C=C)C
  • COC=C
Properties
Chemical formula C3H6O
Molar mass 58.080 g·mol
Density 0.77 g/cm
Melting point −122 °C (−188 °F; 151 K)
Boiling point 6 °C (43 °F; 279 K)
Vapor pressure 157 kPa (20 °C)
Hazards
GHS labelling:
Pictograms GHS02: Flammable
Signal word Danger
Hazard statements H220
Precautionary statements P210, P377, P381, P403
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
2 4 2W
Flash point −60 °C (−76 °F; 213 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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).

Preparation

Methyl vinyl ether can be made by reaction of acetylene and methanol in presence of a base.

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. 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 cycloaddition reactions. 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. 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.

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).

References

  1. ^ Record of Methylvinylether in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 20 April 2008.
  2. David Trimma; Noel Cant; Yun Lei (2009). "Oxygenated fuel additives: The formation of methyl vinyl ether and 1,1-dimethoxyethane by the catalysed reaction of acetylene with methanol". Catalysis Today. 145 (1–2): 163–168. doi:10.1016/j.cattod.2008.04.015.
  3. ^ Ernst Hofmann; Hans‐Joachim Klimisch; René Backes; Regina Vogelsang; Lothar Franz; Robert Feuerhake (2011). "Vinyl Ethers". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a27_435.pub2. ISBN 978-3-527-30673-2.
  4. Gerd Schröder (2012). "Poly(Vinyl Ethers)". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a22_011. ISBN 978-3-527-30673-2.
  5. Longley Jr., R. I.; Emerson, W. S. (1950). "The 1,4-Addition of Vinyl Ethers to α,β-Unsaturated Carbonyl Compounds". J. Am. Chem. Soc. 72 (7): 3079–3081. doi:10.1021/ja01163a076.
  6. Lever Jr., O. W. (1976). "New horizons in carbonyl chemistry: reagents for nucleophilic acylation". Tetrahedron. 32 (16): 1943–1971. doi:10.1016/0040-4020(76)80088-9.
  7. Soderquist, J. A.; Hassner, A. (1980). "Synthetic methods. 15. Unsaturated acyl derivatives of silicon, germanium, and tin from metalated enol ethers". J. Am. Chem. Soc. 102 (5): 1577–1583. doi:10.1021/ja00525a019.
  8. Soderquist, J. A.; Hassner, A. (1980). "Vinylmetalloids. 3. Sila- and germacyclopentan-2-ones from metallated enol ethers". J. Org. Chem. 45 (3): 541–543. doi:10.1021/jo01291a041.
  9. Soderquist, J. A. (1990). "Acetyltrimethylsilane". Org. Synth. 68: 25. doi:10.15227/orgsyn.068.0025.
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