Ethyl iodoacetate
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Ethyl iodoacetate
Other names
Ethyl 2-iodoacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.816
UNII
  • InChI=1S/C4H7IO2/c1-2-7-4(6)3-5/h2-3H2,1H3 checkY
    Key: MFFXVVHUKRKXCI-UHFFFAOYSA-N checkY
  • InChI=1/C4H7IO2/c1-2-7-4(6)3-5/h2-3H2,1H3
    Key: MFFXVVHUKRKXCI-UHFFFAOYAB
  • CCOC(=O)CI
Properties
C4H7IO2
Molar mass 214.002 g·mol−1
Density 1.808 g/mL
Boiling point 179 to 180 °C (354 to 356 °F; 452 to 453 K)
-97.6·10−6 cm3/mol
Hazards
GHS labelling:[1]
GHS05: Corrosive GHS06: Toxic
Danger
H300, H314
P280, P301+P310+P330, P301+P330+P331, P303+P361+P353, P305+P351+P338+P310
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

Ethyl iodoacetate is a chemical compound that is a derivative of ethyl acetate.[2][3] Under normal conditions, the compound is a clear, light yellow to orange liquid.

Applications

Used by the British during World War I, it was codenamed SK gas, for the initials of South Kensington, where it was developed.[4]

Like many alkyl iodides, ethyl iodoacetate is an alkylating agent, which makes it useful in organic synthesis, yet toxic. Ethyl iodoacetate is also a lachrymatory agent.

References

  1. ↑ GHS: Sigma-Aldrich 242934
  2. ↑ "242934 ALDRICH Ethyl iodoacetate". Sigma Aldrich. sigmaaldrich.com. Retrieved 1 June 2017.
  3. ↑ "Ethyl iodoacetate". chemicalbook.com. Retrieved 1 June 2017.
  4. ↑ Timothy T. Marrs; Robert L. Maynard; Frederick Sidell (4 April 2007). Chemical Warfare Agents: Toxicology and Treatment. John Wiley & Sons. pp. 682–. ISBN 978-0-470-06002-5.
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