Ethyl chloroformate

Ethyl chloroformate is an organic compound with the chemical formula ClCO2CH2CH3. It is the ethyl ester of chloroformic acid. It is a colorless, corrosive and highly toxic liquid. It is a reagent used in organic synthesis for the introduction of the ethyl carbamate protecting group[3] and for the formation of carboxylic anhydrides.

Ethyl chloroformate[1]
Skeletal formula of ethyl chloroformate
Ball-and-stick model of the ethyl chloroformate molecule
Names
Preferred IUPAC name
Ethyl carbonochloridate
Other names
  • Cathyl chloride
  • Chloroformic acid ethyl ester
  • Ethyl chlorocarbonate
  • TL-423
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.981
EC Number
  • 208-778-5
RTECS number
  • LQ6125000
UNII
UN number 1182
  • 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
ClCO2CH2CH3
Molar mass 108.52 g·mol−1
Appearance Colorless liquid
Odor Like hydrochloric acid[2]
Density 1.1403 g/cm3
Melting point −81 °C (−114 °F; 192 K)
Boiling point 95 °C (203 °F; 368 K)
Decomposes
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
Flammable
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H225, H302, H314, H330
P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P320, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
4
3
0
W
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, flammable, corrosive substance. It causes severe burns when comes in contact with eyes and/or skin, can be harmful if swallowed or inhaled.[4]

References
  1. Merck Index, 11th Edition, 3742.
  2. https://www.sigmaaldrich.com/GB/en/sds/aldrich/185892
  3. Protective Groups in Organic Synthesis, Third Edition, Theodora W. Greene and Peter G. M. Wuts, pages 504-506, ISBN 0-471-16019-9
  4. PubChem. "Ethyl chloroformate". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-09-04.
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