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Ethyl chloroformate

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Ethyl chloroformate[1]
Skeletal formula of ethyl chloroformate
Ball-and-stick model of the ethyl chloroformate molecule
Names
IUPAC name
chloroformic acid ethyl ester
Other names
Cathyl chloride; Ethyl chlorocarbonate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.981 Edit this at Wikidata
  • InChI=1S/C3H5ClO2/c1-2-6-3(4)5/h2H2,1H3 checkY
    Key: RIFGWPKJUGCATF-UHFFFAOYSA-N checkY
  • InChI=1/C3H5ClO2/c1-2-6-3(4)5/h2H2,1H3
    Key: RIFGWPKJUGCATF-UHFFFAOYAX
  • ClC(=O)OCC
Properties
C3H5ClO2
Molar mass 108.52 g/mol
Appearance Clear liquid
Density 1.1403 g/cm3
Boiling point 95 °C (203 °F; 368 K)
Decomposes
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
Flammable
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
3
0
Flash point 61 °C (142 °F; 334 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ethyl chloroformate is the ethyl ester of chloroformic acid. It is a reagent used in organic synthesis for the introduction of the ethyl carbamate protecting group[2] and for the formation of carboxylic anhydrides. It is capable of producing GABAergic anxiolytic/sedative/anesthetic effects (in order of increasing dose-effect threshold) in sufficient doses but produces potent hemotoxic and neurotoxic effects doses below the anesthetic threshold (roughly equivalent to the anxiolytic threshold) and was therefore never used for medical applications.

References

  1. ^ Merck Index, 11th Edition, 3742.
  2. ^ Protective Groups in Organic Synthesis, Third Edition, Theodora W. Greene and Peter G. M. Wuts, pages 504-506, ISBN 0-471-16019-9
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