Ethyl iodoacetate

{{chembox }} }}
 * Watchedfields = changed
 * verifiedrevid = 426958069
 * Name = Ethyl iodoacetate
 * ImageFile = Ethyl-iodoacetate-2D-skeletal.svg
 * ImageSize = 180px
 * ImageName = Skeletal formula
 * ImageFile1 = Ethyl-iodoacetate-3D-balls.png
 * ImageName1 = Ball-and-stick model
 * PIN = Ethyl iodoacetate
 * OtherNames = Ethyl 2-iodoacetate
 * Section1={{Chembox Identifiers
 * ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 * ChemSpiderID = 11683
 * PubChem = 12183
 * InChI = 1/C4H7IO2/c1-2-7-4(6)3-5/h2-3H2,1H3
 * InChIKey = MFFXVVHUKRKXCI-UHFFFAOYAB
 * StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 * StdInChI = 1S/C4H7IO2/c1-2-7-4(6)3-5/h2-3H2,1H3
 * StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 * StdInChIKey = MFFXVVHUKRKXCI-UHFFFAOYSA-N
 * CASNo_Ref = {{cascite|correct|??}}
 * CASNo = 623-48-3
 * UNII_Ref = {{fdacite|correct|FDA}}
 * UNII = X9ZR7PV2QF
 * SMILES = CCOC(=O)CI
 * Section2={{Chembox Properties
 * Formula = {{chem2|ICH2CO2CH2CH3}}
 * C=4 | H=7 | I=1 | O=2
 * Density = 1.808 g/mL
 * Appearance = Clear, light yellow to orange liquid
 * MeltingPt =
 * BoilingPtC = 179 to 180
 * BoilingPt_notes =
 * MagSus = −97.6·10{{sup|−6}} cm{{sup|3}}/mol
 * Section7={{Chembox Hazards
 * GHSPictograms = {{GHS05}}{{GHS06}}
 * GHSSignalWord = danger
 * HPhrases = {{HPhrases|H300|H314}}
 * PPhrases = {{PPhrases|P280|P301+P310+P330|P301+P330+P331|P303+P361+P353|P305+P351+P338+P310}}
 * GHS_ref = 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.

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.