Revision as of 02:27, 9 February 2011 edit65.94.102.21 (talk)No edit summary← Previous edit |
Latest revision as of 17:10, 22 October 2024 edit undo64.92.68.154 (talk) inserted {{citation needed]] flag after discussing ways to synthesize EtI |
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| verifiedrevid = 396487543 |
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| verifiedrevid = 412840709 |
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| ImageFile = Iodoethane FormulaV1.svg |
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| Name = ethyl iodide |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = Iodoethane-skeletal.png |
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| ImageSize1 = 150px |
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| ImageSize = 100 |
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| ImageName = Skeletal formula of ethyl iodide |
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| ImageName1 = |
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| ImageFile = ethylIodide.png |
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| ImageFileL1 = Iodoethane-3D-balls.png |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageSize =200px |
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| ImageNameL1 = Ball and stick model of ethyl iodide |
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| ImageName = |
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| ImageFileR1 = ethylIodide.png |
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| IUPACName = iodoethane |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| OtherNames = iodoethane |
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| ImageNameR1 = Spacefill model of ethyl iodide |
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| Section1 = {{Chembox Identifiers |
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| 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> |
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| SMILES = ICC |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo = 75-03-6 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 59PO05D39L |
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| PubChem = 6340 |
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| ChemSpiderID = 6100 |
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| ChemSpiderID = 6100 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChI = 1/C2H5I/c1-2-3/h2H2,1H3 |
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| EINECS = 200-833-1 |
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| InChIKey = HVTICUPFWKNHNG-UHFFFAOYAT |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 42487 |
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| ChEMBL = 1232588 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| RTECS = KI4750000 |
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| Beilstein = 505934 |
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| SMILES = CCI |
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| StdInChI = 1S/C2H5I/c1-2-3/h2H2,1H3 |
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| StdInChI = 1S/C2H5I/c1-2-3/h2H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = HVTICUPFWKNHNG-UHFFFAOYSA-N |
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| StdInChIKey = HVTICUPFWKNHNG-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo = 75-03-6 |
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}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|Section2={{Chembox Properties |
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| RTECS = KI4750000 |
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| C=2 | H=5 | I=1 |
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| Appearance = Colourless liquid |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>2</sub>H<sub>5</sub>I |
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| Density = 1.940 g mL<sup>−1</sup> |
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| MolarMass = 155.97 |
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| MeltingPtK = 162.05 |
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| BoilingPtK = 344.6 to 346.4 |
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| Appearance = Colourless liquid |
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| Solubility = 4 g L<sup>−1</sup> (at 20 °C) |
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| Density = 1.950 g/cm^3 |
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| Solvent1 = ethanol |
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| Solubility = 0.4 g/100 ml at 20 °C |
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| Solubility1 = fully ] |
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| Solubility1 = Miscible |
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| Solvent2 = diethyl ether |
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| Solvent1 = ethanol |
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| Solubility2 = fully ] |
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| Solubility2 = Miscible |
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| LogP = 2.119 |
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| Solvent2 = diethyl ether |
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| RefractIndex = 1.3903 |
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| VaporPressure = 17.7 kPa |
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| HenryConstant = 1.8 μmol Pa<sup>−1</sup> kg<sup>−1</sup> |
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| MeltingPtC = -110.9 |
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| RefractIndex = 1.513–1.514 |
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| BoilingPtC = 72.4 |
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| Viscosity = 5.925 mPa s (at 20 °C) |
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| pKa = |
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| MagSus = -69.7·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Viscosity = 7.269 c] at 0 °C<br/>5.925 c] at 20 °C |
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}} |
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| Dipole = |
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|Section3={{Chembox Thermochemistry |
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}} |
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| DeltaHf = −39.9–−38.3 kJ mol<sup>−1</sup> |
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| Section7 = {{Chembox Hazards |
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| DeltaHc = −1.4629–−1.4621 MJ mol<sup>−1</sup> |
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| MainHazards = Possible teratogen. Possible risk of harm to the unborn child. Vesicant. Harmful by inhalation, ingestion and through skin contact. May cause sensitization. Narcotic. |
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| HeatCapacity = 109.7 J K<sup>−1</sup> mol<sup>−1</sup> |
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| FlashPt = |
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}} |
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| NFPA-H = 2 |
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|Section4={{Chembox Hazards |
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| NFPA-F = 1 |
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| GHSPictograms = {{GHS exclamation mark}} {{GHS health hazard}} |
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| NFPA-R = 1 |
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| GHSSignalWord = '''DANGER''' |
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| NFPA-O = |
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| HPhrases = {{H-phrases|302|315|317|319|334|335}} |
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| RPhrases = {{R23}} {{R24}} {{R25}} {{R42}} {{R43}} {{R63}} |
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| PPhrases = {{P-phrases|261|280|305+351+338|342+311}} |
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| SPhrases = {{S45}} {{S26}} {{S36}} {{S37}} {{S39}} {{S23}} |
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| NFPA-H = 2 |
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| ExternalMSDS = |
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| NFPA-F = 1 |
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| NFPA-R = 1 |
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| Section8 = {{Chembox Related |
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| FlashPtC = 72 |
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| Function = ]s |
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| LD50 = 330 g m<sup>−3</sup> <small>(oral, rat)</small> |
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| OtherFunctn = ]<br>]<br>]<br>]}} |
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|Section5={{Chembox Related |
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| OtherFunction_label = iodoalkanes |
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| OtherFunction = {{Unbulleted list|]|]|]|]|]|]}} |
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| OtherCompounds = {{Unbulleted list|]|]|]}} |
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'''Ethyl iodide''' (also ''iodoethane'') is a ], ] ]. It has the chemical formula C<sub>2</sub>H<sub>5</sub>I and is prepared by heating ] with ] and ].<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. |
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'''Ethyl iodide''' (also '''iodoethane''') is a ] ] ]. It has the chemical formula C<sub>2</sub>H<sub>5</sub>I and is prepared by heating ] with ] and ].<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. |
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It may also be prepared by reaction between ] and ethanol distilling off the ethyl iodide {{Citation needed|reason=citation needed for this reaction|date=October 2024}}. 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. |
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Ethyl iodide is very good with alkylation reactions. It is also used as the hydrogen radical promoter. |
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==References== |
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{{reflist|1}} |
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Because iodide is a good ], ethyl iodide is an excellent ethylating agent. It is also used as the hydrogen radical promoter. |
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==Production== |
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Ethyl iodide is prepared by using red ], absolute ] and ]. The iodine dissolves in the ethanol, where it reacts with the solid phosphorus to form ].<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. |
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:3 C<sub>2</sub>H<sub>5</sub>OH + PI<sub>3</sub> → 3 C<sub>2</sub>H<sub>5</sub>I + H<sub>3</sub>PO<sub>3</sub> |
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{{organohalide-stub}} |
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The crude product is purified by distillation. |
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==References== |
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{{Reflist|1}} |
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{{Authority control}} |
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