Ethyl iodoacetate

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.

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	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)
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
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

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.