Ethyl vinyl ether is an organic compound with the chemical formula CH 3 CH 2 OCH=CH 2. They are increasingly used in radiation curing systems because of a lower toxicity profile than the commonly used acrylic monomers. Chem., Univ. It is the simplest enol ether that is liquid at room temperature. 8,21,151,152 The mechanism for chain transfer is shown in Scheme 9 for the case of α-benzyloxystyrene (15).The driving force for fragmentation is provided by formation of a strong carbonyl double bond. COVID-19 is an emerging, rapidly evolving situation. Vinyl ether | C4H6O | CID 8024 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. The alkene can be deprotonated at the vinyl carbon adjacent to the oxygen. [5] Its reaction with acrolein is the first step in the commercial synthesis of glutaraldehyde. Methyl vinyl ether can be made by reaction of acetylene and methanol in presence of a base.[2][3]. It is prone to polymerization, leading to formation of polyvinyl ethers. Title Journal or Book Year; 17O NMR spectra of vinyl ethers : Magnetic Resonance in Chemistry: 1994 ; 17O NMR investigation ofp,π-interactions in α,β-unsaturated and aromatic ethers Compound with free spectra: 6 NMR, 6 FTIR, and 1 Raman, http://spectrabase.com/compound/12z06QZ3zii, View entire compound with free spectra: 6 NMR, 6 FTIR, and 1 Raman, 17O NMR investigation ofp,π-interactions in α,β-unsaturated and aromatic ethers, InChI=1S/C6H12O/c1-4-7-5-6(2)3/h4,6H,1,5H2,2-3H3. It is also important that R is a good radical leaving group. It is used as a synthetic building block, as is the related compound ethyl vinyl ether (a liquid at room temperature). 124 The fast living cationic polymerization of vinyl ethers with SnCl 4 combined with EtAlCl 2 in the presence of an ester as an added base was reported. The alkene portion of the molecule is reactive in many ways. Vinyl ethers (1, X = CH 2, A = O) can be very effective addition–fragmentation chain transfer agents. Use of ethyl vinyl ether in the synthesis of glutaraldehyde. Copyright © 1980, 1981-2020 John Wiley & Sons, Inc. All Rights Reserved. Poly(vinyl ether)s with a T g as high as 100 °C have been obtained in the living cationic polymerization of vinyl ethers with a bulky tricyclodecane or tricyclodecene unit using HCl/ZnCl 2 in toluene at –30 °C. Methyl vinyl ether also participates in [4+2] cycloaddition reactions. A colorless gas, it is the simplest enol ether. It is used as a synthetic building block and a monomer. SpectraBase Compound ID=12z06QZ3zii Wiley SpectraBase; In the micronucleus test in mice, vinyl methyl ether did not produce a clastogenic effect following 5 exposures of 25,000 ppm. http://spectrabase.com/compound/12z06QZ3zii All Rights Reserved. The acute LD50 for methyl vinyl ether is greater than 4 g/kg (rats, oral). of Vienna. Copyright © 2020 by John Wiley & Sons, Inc., or related companies. Methyl vinyl ether is an organic compound with the chemical formula CH 3 OCH=CH 2.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). [3], Except where otherwise noted, data are given for materials in their, Institute for Occupational Safety and Health, https://en.wikipedia.org/w/index.php?title=Methyl_vinyl_ether&oldid=943277933, Chemical articles with multiple compound IDs, Multiple chemicals in an infobox that need indexing, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, This page was last edited on 29 February 2020, at 23:16. of Org. Aldrich Chemical Company, Inc., Milwaukee, Wisconsin, Chloroform-d; Reference=TMS Spectrometer= Varian CFT-20, Gaf Materials Corporation, Wayne, New Jersey. [7][8][9], The toxicity of vinyl ethers has been heavily investigated because divinyl ether has been used as an anesthetic. (accessed Nov 13, 2020). Copyright © 2009-2020 John Wiley & Sons, Inc. All Rights Reserved. Copyright © 2016-2020 W. Robien, Inst. Polymerization is typically initiated with Lewis acids such as boron trifluoride. Vinyl ethers undergo radical initiated copolymerization in the presence of specific monomers such as maleates, fumarates, and acrylics. This site uses cookies. By continuing to browse the site you are agreeing to our use of cookies. All rights reserved. Vinyl ethers undergo homopolymerization via a cationic mechanism. Methyl vinyl ether was not mutagenic on Salmonella typhimurium TA98, TA100, TA1535 and TA1537, and Escherichia` coli WP2 uvrA with or without metabolic activation. Methyl vinyl ether is an organic compound with the chemical formula CH3OCH=CH2. [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. Copyright © 2012-2020 John Wiley & Sons, Inc. All Rights Reserved. [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.

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