Ethyl chloroformate

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.

Ethyl chloroformate[1]
Names
Preferred IUPAC name
Ethyl carbonochloridate
Other names
Chloroformic acid ethyl ester
Cathyl chloride
Ethyl chlorocarbonate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.981
UNII
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 (fire diamond)
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. gasolineHealth code 4: Very short exposure could cause death or major residual injury. E.g. VX gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
4
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).
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Infobox references


Preparation

Ethyl chloroformate can be prepared using ethanol and phosgene:

Safety

Ethyl chloroformate is a highly toxic substance. It causes severe burns when comes in contact with eyes and/or skin, can be fatal if swallowed or inhaled.[3]

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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
  3. PubChem. "Ethyl chloroformate". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-09-04.
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