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;
UNII	X9ZR7PV2QF ;
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	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 cm3/mol
Hazards
	GHS labelling:
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). verify (what is ?) Infobox references

Ethyl iodoacetate is an organic compound with the chemical formula I C H₂CO₂CH₂CH₃. 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

^ GHS: Sigma-Aldrich 242934
^ "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.

[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.

[MarrsMaynard2007-4] 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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