# Ethyl vinyl ether

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Ethyl vinyl ether Names Preferred IUPAC name Ethoxyethene Other names Ethoxyethylene, Vinamar Identifiers CAS Number 109-92-2 3D model (JSmol) Interactive image ChEMBL ChEMBL116745 ChemSpider 7732 ECHA InfoCard 100.003.382 EC Number 203-718-4 PubChem CID 8023 RTECS number KO0710000 UNII 6235C9592H UN number 1302 CompTox Dashboard (EPA) DTXSID3029609 InChI InChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3 Key: FJKIXWOMBXYWOQ-UHFFFAOYSA-N SMILES CCOC=C Properties Chemical formula C4H8O Molar mass 72.107 g·mol−1 Appearance colorless liquid Density 0.7589 g/mL Melting point −116 °C (−177 °F; 157 K) Boiling point 33 °C (91 °F; 306 K) Solubility in water 8.3 g/L at 15°C Hazards GHS labelling: Pictograms Signal word Warning Hazard statements H225, H319, H335, H412 Precautionary statements P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P303+P361+P353, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501 Autoignition temperature 202 °C (396 °F; 475 K) Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

**Ethyl vinyl ether** is an [organic compound](/source/Organic_compound) with the chemical formula CH3CH2OCH=CH2. It is the simplest [enol ether](/source/Enol_ether) that is liquid at room temperature. It is used as a synthetic building block and a [monomer](/source/Monomer).

Use of ethyl vinyl ether in the synthesis of glutaraldehyde.

## Preparation and reactions

Ethyl vinyl ether is made by reaction of [acetylene](/source/Acetylene) and [ethanol](/source/Ethanol) in presence of a base.[1]

The alkene portion of the molecule is reactive in many ways. It is prone to [polymerization](/source/Polymerization), leading to formation of [polyvinyl ethers](/source/Polyvinyl_ether). Polymerization is typically initiated with [Lewis acids](/source/Lewis_acid) such as [boron trifluoride](/source/Boron_trifluoride).[2]

Ethyl vinyl ether participates in many reactions of interest to [organic synthesis](/source/Organic_synthesis).[3] With catalytic amounts of acids, ethyl vinyl ether adds to alcohols to give the mixed acetal:

- EtOCH=CH2 + ROH → EtOCH(OR)CH3

This alcohol protection reaction is akin to the behavior of [dihydropyran](/source/Dihydropyran).

Ethyl vinyl ether also participates in inverse demand [4+2] [cycloaddition](/source/Cycloaddition) reactions.

Deprotonation with [butyl lithium](/source/Butyl_lithium) gives the acetyl anion equivalent:

- EtOCH=CH2 + BuLi → EtOC(Li)=CH2 + BuH

## Toxicity

The toxicity of vinyl ethers has been heavily investigated because they have been used as [inhalation anesthetics](/source/Inhalation_anesthetic). The acute [LD50](/source/Median_lethal_dose) for the closely related [methyl vinyl ether](/source/Methyl_vinyl_ether) is greater than 4 g/kg (rats, oral).[1]

## References

1. ^ [***a***](#cite_ref-Ullm_1-0) [***b***](#cite_ref-Ullm_1-1) Ernst Hofmann; Hans‐Joachim Klimisch; René Backes; Regina Vogelsang; Lothar Franz; Robert Feuerhake (2011). "Vinyl Ethers". *[Ullmann's Encyclopedia of Industrial Chemistry](/source/Ullmann's_Encyclopedia_of_Industrial_Chemistry)*. Weinheim: Wiley-VCH. [doi](/source/Doi_(identifier)):[10.1002/14356007.a27_435.pub](https://doi.org/10.1002%2F14356007.a27_435.pub). [ISBN](/source/ISBN_(identifier)) [978-3-527-30673-2](https://en.wikipedia.org/wiki/Special:BookSources/978-3-527-30673-2).

1. **[^](#cite_ref-2)** Gerd Schröder (2012). "Poly(Vinyl Ethers)". *[Ullmann's Encyclopedia of Industrial Chemistry](/source/Ullmann's_Encyclopedia_of_Industrial_Chemistry)*. Weinheim: Wiley-VCH. [doi](/source/Doi_(identifier)):[10.1002/14356007.a22_011](https://doi.org/10.1002%2F14356007.a22_011). [ISBN](/source/ISBN_(identifier)) [978-3-527-30673-2](https://en.wikipedia.org/wiki/Special:BookSources/978-3-527-30673-2).

1. **[^](#cite_ref-eEROS_3-0)** Percy S. Manchand (2001). "Ethyl Vinyl Ether". *EEROS*. [doi](/source/Doi_(identifier)):[10.1002/047084289X.re125](https://doi.org/10.1002%2F047084289X.re125). [ISBN](/source/ISBN_(identifier)) [0-471-93623-5](https://en.wikipedia.org/wiki/Special:BookSources/0-471-93623-5).

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Adapted from the Wikipedia article [Ethyl vinyl ether](https://en.wikipedia.org/wiki/Ethyl_vinyl_ether) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Ethyl_vinyl_ether?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.