Ethyl iodoacetate

Ethyl iodoacetate

Names
Preferred IUPAC name Ethyl iodoacetate
Other names Ethyl 2-iodoacetate
Identifiers
CAS Number	623-48-3^Y
3D model (JSmol)	Interactive image
ChemSpider	11683^Y
ECHA InfoCard	100.009.816
PubChem CID	12183
UNII	X9ZR7PV2QF^Y
CompTox Dashboard (EPA)	DTXSID5060770
InChI InChI=1S/C4H7IO2/c1-2-7-4(6)3-5/h2-3H2,1H3^Y Key: MFFXVVHUKRKXCI-UHFFFAOYSA-N^Y InChI=1/C4H7IO2/c1-2-7-4(6)3-5/h2-3H2,1H3 Key: MFFXVVHUKRKXCI-UHFFFAOYAB
SMILES CCOC(=O)CI
Properties
Chemical formula	ICH2CO2CH2CH3
Molar mass	214.002 g·mol^−1
Appearance	Clear, light yellow to orange liquid
Density	1.808 g/mL
Boiling point	179 to 180 °C (354 to 356 °F; 452 to 453 K)
Magnetic susceptibility (χ)	−97.6·10^−6 cm^3/mol
Hazards
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H300, H314
Precautionary statements	P280, P301+P310+P330, P301+P330+P331, P303+P361+P353, P305+P351+P338+P310
Related compounds
Related esters	Methyl bromoacetate Ethyl 3-bromopropionate Ethyl chloroacetate Ethyl bromoacetate Ethyl bromodifluoroacetate Ethyl acetoacetate
Related compounds	Iodoacetic acid Pepper spray Chloropicrin
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

Ethyl iodoacetate is an organic compound with the chemical formula ICH₂CO₂CH₂CH₃. It 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.