Ethyl iodide

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 412840709

| ImageFile = Iodoethane FormulaV1.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 100

| ImageName = Skeletal formula of ethyl iodide

| ImageFileL1 = Iodoethane-3D-balls.png

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageNameL1 = Ball and stick model of ethyl iodide

| ImageFileR1 = ethylIodide.png

| ImageFileR1_Ref = {{chemboximage|correct|??}}

| ImageNameR1 = Spacefill model of ethyl iodide

| PIN = Iodoethane{{Cite web|title=iodoethane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6340&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=29 February 2012|location=USA|date=26 March 2005|at=Identification and Related Records}}

|Section1={{Chembox Identifiers

| CASNo = 75-03-6

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 59PO05D39L

| PubChem = 6340

| ChemSpiderID = 6100

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 200-833-1

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 42487

| ChEMBL = 1232588

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| RTECS = KI4750000

| Beilstein = 505934

| SMILES = CCI

| StdInChI = 1S/C2H5I/c1-2-3/h2H2,1H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HVTICUPFWKNHNG-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C=2 | H=5 | I=1

| Appearance = Colourless liquid

| Density = 1.940 g mL⁻¹

| MeltingPtK = 162.05

| BoilingPtK = 344.6 to 346.4

| Solubility = 4 g L⁻¹ (at 20 °C)

| Solvent1 = ethanol

| Solubility1 = Miscible

| Solvent2 = diethyl ether

| Solubility2 = Miscible

| LogP = 2.119

| VaporPressure = 17.7 kPa

| HenryConstant = 1.8 μmol Pa⁻¹ kg⁻¹

| RefractIndex = 1.513–1.514

| Viscosity = 5.925 mPa s (at 20 °C)

| MagSus = −69.7·10⁻⁶ cm³/mol

}}

|Section3={{Chembox Thermochemistry

| DeltaHf = −39.9 to −38.3 kJ mol⁻¹

| DeltaHc = −1.4629 to −1.4621 MJ mol⁻¹

| HeatCapacity = 109.7 J K⁻¹ mol⁻¹

}}

|Section4={{Chembox Hazards

| GHSPictograms = {{GHS exclamation mark}} {{GHS health hazard}}

| GHSSignalWord = DANGER

| HPhrases = {{H-phrases|302|315|317|319|334|335}}

| PPhrases = {{P-phrases|261|280|305+351+338|342+311}}

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 1

| FlashPtC = 72

| LD50 = 330 g m⁻³ (oral, rat)

}}

|Section5={{Chembox Related

| OtherFunction_label = iodoalkanes

| OtherFunction = {{Unbulleted list|Methyl iodide|Diiodomethane|Iodoform|Carbon tetraiodide|n-Propyl iodide|Isopropyl iodide}}

| OtherCompounds = {{Unbulleted list|Pimagedine|Guanidine|Diiodohydroxypropane}}

}}

}}

Ethyl iodide (also iodoethane) is a colorless flammable chemical compound. It has the chemical formula C₂H₅I and is prepared by heating ethanol with iodine and phosphorus.Merck Index of Chemicals and Drugs, 9th ed., monograph 3753 On contact with air, especially on the effect of light, it decomposes and turns yellow or reddish from dissolved iodine.

It may also be prepared by the reaction between hydroiodic acid and ethanol, typically by generating the hydroiodic acid in situ via an iodide salt (such as sodium iodide) and an acid (such as sulfuric acid), after which the ethyl iodide is distilled off. Ethyl iodide should be stored in the presence of copper powder to avoid rapid decomposition, though even with this method samples do not last more than 1 year.

File:Ethyl Iodide production.jpg{{clear left}}

Because iodide is a good leaving group, ethyl iodide is an excellent ethylating agent. It is also used as the hydrogen radical promoter.