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Ethyl chloroformate

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Ethyl chloroformate
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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.981 Edit this at Wikidata
EC Number
  • 208-778-5
PubChem CID
RTECS number
  • LQ6125000
UNII
UN number 1182
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H5ClO2/c1-2-6-3(4)5/h2H2,1H3Key: RIFGWPKJUGCATF-UHFFFAOYSA-N
  • InChI=1/C3H5ClO2/c1-2-6-3(4)5/h2H2,1H3Key: RIFGWPKJUGCATF-UHFFFAOYAX
SMILES
  • ClC(=O)OCC
Properties
Chemical formula ClCO2CH2CH3
Molar mass 108.52 g·mol
Appearance Colorless liquid
Odor Like hydrochloric acid
Density 1.1403 g/cm
Melting point −81 °C (−114 °F; 192 K)
Boiling point 95 °C (203 °F; 368 K)
Solubility in water Decomposes
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Corrosive
Flammable
GHS labelling:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Signal word Danger
Hazard statements H225, H302, H314, H330
Precautionary statements 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 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 hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
4 3 0W
Flash point 61 °C (142 °F; 334 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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 and for the formation of carboxylic anhydrides.

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.

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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