Chemistry:Ethyl chloroformate

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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
EC Number
  • 208-778-5
RTECS number
  • LQ6125000
UNII
UN number 1182
Properties
ClCO
2CH
2CH
3
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
Main hazards Corrosive
Flammable
GHS pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Harmful
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 acidNFPA 704 four-colored diamond
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
Tracking categories (test):

Ethyl chloroformate is an organic compound with the chemical formula ClCO
2CH
2CH
3. 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.

Preparation

Ethyl chloroformate can be prepared using ethanol and phosgene:

Synthesis Ethylchloroformiate A.svg

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" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/10928. 



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