Ethyl iodide: Difference between revisions

{{Chembox

| Verifiedfields = 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<ref>{{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}}</ref>

|Section1={{Chembox Identifiers

| CASNo = 75-03-6

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

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

| UNII = 59PO05D39L

| PubChem = 6340

| 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_Ref = {{stdinchicite|correct|chemspider}}

| 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–−38.3 kJ mol⁻¹

| DeltaHc = −1.4629–−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 <small>(oral, rat)</small>

}}

|Section5={{Chembox Related

| OtherFunction_label = iodoalkanes

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

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

}}

'''Ethyl iodide''' (also '''iodoethane''') is a [[transparency and translucency|colorless]] [[flammable]] [[chemical compound]]. It has the chemical formula C₂H₅I and is prepared by heating [[ethanol]] with [[iodine]] and [[phosphorus]].<ref name="merck">''Merck Index of Chemicals and Drugs'', 9th ed., monograph 3753</ref> 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 reaction between [[hydroiodic acid]] and ethanol distilling off the ethyl iodide. 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|thumb|left|Ethyl iodide distillation. It has a greenish color due to decomposition.]]{{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.

==Production==

Ethyl iodide is prepared by using red [[phosphorus]], absolute [[ethanol]] and [[iodine]]. The iodine dissolves in the ethanol, where it reacts with the solid phosphorus to form [[phosphorus triiodide]].<ref>{{cite book | author = Csámpai, A | author2 = Láng, E | author3 = Majer, Zs | author4 = Orosz, Gy | author5 = Rábai, J | author6 = Ruff, F | author7 = Schlosser, G | author8 = Szabó, D | author9 = Vass, E | title = Szerves Kémiai Praktikum | page = 274 | publisher = Eötvös kiadó | year = 2012 | isbn = 978-963-312-129-0}}</ref> During this process, the temperature is controlled.

:3 C₂H₅OH + PI₃ → 3 C₂H₅I + H₃PO₃

The crude product is purified by distillation.

==References==

{{Reflist|1}}

{{Authority control}}

[[Category:Iodoalkanes]]

[[Category:Ethylating agents]]

[[Category:Organoiodides]]