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
EC Number
  • 208-778-5
RTECS number
  • LQ6125000
UNII
UN number 1182
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
GHS pictograms
GHS Signal word Danger
H225, H302, H314, H330
P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+312, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P320, P321, P330, P363, P370+378, P403+233, P403+235
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 hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
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).
Y verify (what is YN ?)
Infobox references


Preparation

Ethyl chloroformate can be prepared using ethanol and phosgene:

Safety

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

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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