Ethyl iodoacetate

Ethyl iodoacetate
Names
	Preferred IUPAC name Ethyl iodoacetate
	Other names Ethyl 2-iodoacetate
Identifiers
CAS Number	623-48-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	11683 ;
ECHA InfoCard	100.009.816
PubChem CID	12183;
CompTox Dashboard (EPA)	DTXSID5060770 ;
	InChI InChI=1S/C4H7IO2/c1-2-7-4(6)3-5/h2-3H2,1H3 Key: MFFXVVHUKRKXCI-UHFFFAOYSA-N ; 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 cm3/mol
Hazards
EU classification (DSD) (outdated)	T
	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.[1][2] 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.[3]

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

"242934 ALDRICH Ethyl iodoacetate". Sigma Aldrich. sigmaaldrich.com. Retrieved 1 June 2017.
"Ethyl iodoacetate". chemicalbook.com. Retrieved 1 June 2017.
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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[1] "242934 ALDRICH Ethyl iodoacetate". Sigma Aldrich. sigmaaldrich.com. Retrieved 1 June 2017.

[2] "Ethyl iodoacetate". chemicalbook.com. Retrieved 1 June 2017.

[MarrsMaynard2007-3] 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.