{{Chembox | ImageFile = Ethyl vinylether.svg | ImageSize = | ImageAlt = | PIN = Ethoxyethene | OtherNames = Ethoxyethylene, ''Vinamar'' |Section1={{Chembox Identifiers | CASNo = 109-92-2 | ChemSpiderID = 7732 | PubChem = 8023 | EC_number = 203-718-4 | RTECS = KO0710000 | UNNumber = 1302 | UNII = 6235C9592H | ChEMBL = 116745 | StdInChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3 | StdInChIKey = FJKIXWOMBXYWOQ-UHFFFAOYSA-N | SMILES = CCOC=C }} |Section2={{Chembox Properties | C=4|H=8|O=1 | MolarMass = | Appearance = colorless liquid | Density = 0.7589 g/mL | MeltingPtC = −116 | BoilingPtC = 33 | Solubility = 8.3 g/L at 15°C }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPtC = 202 | GHSPictograms = {{GHS02}}{{GHS07}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|225|319|335|412}} | PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|273|280|303+361+353|304+340|305+351+338|312|337+313|370+378|403+233|403+235|405|501}} }} }}
'''Ethyl vinyl ether''' is an [[organic compound]] with the chemical formula CH<sub>3</sub>CH<sub>2</sub>OCH=CH<sub>2</sub>. It is the simplest [[enol ether]] that is liquid at room temperature. It is used as a synthetic building block and a [[monomer]]. [[File:Glutaraldehyde synthesis.svg|160px|thumb|left|Use of ethyl vinyl ether in the synthesis of glutaraldehyde.]]
==Preparation and reactions== Ethyl vinyl ether is made by reaction of [[acetylene]] and [[ethanol]] in presence of a base.<ref name=Ullm>{{Ullmann|title=Vinyl Ethers |author=Ernst Hofmann |author2=Hans‐Joachim Klimisch |author3=René Backes |author4=Regina Vogelsang |author5=Lothar Franz |author6=Robert Feuerhake |year=2011|doi=10.1002/14356007.a27_435.pub}}</ref>
The alkene portion of the molecule is reactive in many ways. It is prone to [[polymerization]], leading to formation of [[polyvinyl ether]]s. Polymerization is typically initiated with [[Lewis acid]]s such as [[boron trifluoride]].<ref>{{Ullmann|title=Poly(Vinyl Ethers)|author=Gerd Schröder|year=2012|doi=10.1002/14356007.a22_011}}</ref>
Ethyl vinyl ether participates in many reactions of interest to [[organic synthesis]].<ref name=eEROS>{{cite journal|journal=EEROS|title=Ethyl Vinyl Ether|author=Percy S. Manchand|year=2001|doi=10.1002/047084289X.re125|isbn=0-471-93623-5}}</ref> With catalytic amounts of acids, ethyl vinyl ether adds to alcohols to give the mixed acetal: :EtOCH=CH<sub>2</sub> + ROH → EtOCH(OR)CH<sub>3</sub> This alcohol protection reaction is akin to the behavior of [[dihydropyran]].
Ethyl vinyl ether also participates in inverse demand [4+2] [[cycloaddition]] reactions.
Deprotonation with [[butyl lithium]] gives the acetyl anion equivalent: :EtOCH=CH<sub>2</sub> + BuLi → EtOC(Li)=CH<sub>2</sub> + BuH
==Toxicity== The toxicity of vinyl ethers has been heavily investigated because they have been used as [[inhalation anesthetic]]s. The acute {{LD50}} for the closely related [[methyl vinyl ether]] is greater than 4 g/kg (rats, oral).<ref name=Ullm/>
== References == {{reflist}}
[[Category:Vinyl ethers]] [[Category:Ethyl compounds]]