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

EC Number |

* 203-718-4

PubChem CID

* 8023

RTECS number |

* KO0710000

UNII |

* 6235C9592H

UN number | 1302

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 pictograms |
GHS Signal word | Warning

GHS hazard statements

| H225, H319, H335, H412

GHS precautionary statements

| P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P303+361+353, P304+340, P305+351+338, P312, P337+313, P370+378, P403+233, P403+235, 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

Ethyl vinyl ether is an organic compound with the chemical formula CH3CH2OCH=CH2. It is the simplest enol ether that is liquid at room temperature. It is used as a synthetic building block and a monomer.

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.[1]

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.[2]

Ethyl vinyl ether participates in many reactions of interest to 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.

Ethyl vinyl ether also participates in inverse demand [4+2] cycloaddition reactions.

Deprotonation with 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. The acute LD50 for the closely related methyl vinyl ether is greater than 4 g/kg (rats, oral).[1]

## References

1. ↑ 1.0 1.1 Ernst Hofmann; Hans‐Joachim Klimisch; René Backes; Regina Vogelsang; Lothar Franz; Robert Feuerhake (2011). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_435.pub.
2. ↑ Gerd Schröder (2012). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_011.
3. ↑ Percy S. Manchand (2001). "Ethyl Vinyl Ether". EEROS. doi:10.1002/047084289X.re125. ISBN 0-471-93623-5.

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*[CID]: Compound ID
*[H225]: Highly flammable liquid and vapour
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[H412]: Harmful to aquatic life with long lasting effects
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P337+313]: Get medical advice/attention
*[P370+378]: In case of fire: Use … for extinction
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P403+235]: Store in a well ventilated place. Keep cool
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …