Ethyl chloroformate

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
541-41-3 Yes
ChemSpider 10465 Yes
Jmol-3D images Image
PubChem 10928
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
Main hazards Corrosive
Flammable
NFPA 704
Flammability code 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., gasoline) Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
3
4
0
Flash point 61 °C (142 °F; 334 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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