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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.161
UNII
Properties
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
F+
R-phrases (outdated) R12
S-phrases (outdated) (S2), S9, S16, S33
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]

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.CS1 maint: uses authors parameter (link)
  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 978-3527306732.CS1 maint: uses authors parameter (link)
  4. Gerd Schröder (2012). "Poly(Vinyl Ethers)". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a22_011. ISBN 978-3527306732.CS1 maint: uses authors parameter (link)
  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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