Ethyl iodoacetate
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| Preferred IUPAC name
Ethyl iodoacetate | |
| Other names
Ethyl 2-iodoacetate | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.009.816 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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) |
| −97.6·10−6 cm3/mol | |
| Hazards | |
| GHS labelling:[1] | |
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| Danger | |
| H300, H314 | |
| P280, P301+P310+P330, P301+P330+P331, P303+P361+P353, P305+P351+P338+P310 | |
| Related compounds | |
Related esters |
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Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.