Misplaced Pages

Ethyl iodide: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
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 
(68 intermediate revisions by 46 users not shown)
Line 1: Line 1:
{{chembox {{Chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 396487543 | verifiedrevid = 412840709
| ImageFile = Iodoethane FormulaV1.svg
| Name = ethyl iodide
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile1 = Iodoethane-skeletal.png
| ImageSize1 = 150px | ImageSize = 100
| ImageName = Skeletal formula of ethyl iodide
| ImageName1 =
| ImageFile = ethylIodide.png | ImageFileL1 = Iodoethane-3D-balls.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageSize =200px
| ImageNameL1 = Ball and stick model of ethyl iodide
| ImageName =
| ImageFileR1 = ethylIodide.png
| IUPACName = iodoethane
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| OtherNames = iodoethane
| ImageNameR1 = Spacefill model of ethyl iodide
| Section1 = {{Chembox Identifiers
| 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>
| SMILES = ICC
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| CASNo = 75-03-6
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 59PO05D39L
| PubChem = 6340
| ChemSpiderID = 6100 | ChemSpiderID = 6100
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| InChI = 1/C2H5I/c1-2-3/h2H2,1H3
| EINECS = 200-833-1
| InChIKey = HVTICUPFWKNHNG-UHFFFAOYAT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 = 1S/C2H5I/c1-2-3/h2H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HVTICUPFWKNHNG-UHFFFAOYSA-N | StdInChIKey = HVTICUPFWKNHNG-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| CASNo = 75-03-6
}}
| CASNo_Ref = {{cascite|correct|CAS}}
|Section2={{Chembox Properties
| RTECS = KI4750000
| C=2 | H=5 | I=1
}}
| Appearance = Colourless liquid
| Section2 = {{Chembox Properties
| Formula = C<sub>2</sub>H<sub>5</sub>I | Density = 1.940 g mL<sup>−1</sup>
| MolarMass = 155.97 | MeltingPtK = 162.05
| BoilingPtK = 344.6 to 346.4
| Appearance = Colourless liquid
| Solubility = 4 g L<sup>−1</sup> (at 20 °C)
| Density = 1.950 g/cm^3
| Solvent1 = ethanol
| Solubility = 0.4 g/100 ml at 20 °C
| Solubility1 = fully ] | Solubility1 = Miscible
| Solvent2 = diethyl ether
| Solvent1 = ethanol
| Solubility2 = fully ] | Solubility2 = Miscible
| LogP = 2.119
| Solvent2 = diethyl ether
| RefractIndex = 1.3903 | VaporPressure = 17.7 kPa
| HenryConstant = 1.8 μmol Pa<sup>−1</sup> kg<sup>−1</sup>
| MeltingPtC = -110.9
| RefractIndex = 1.513–1.514
| BoilingPtC = 72.4
| Viscosity = 5.925 mPa s (at 20 °C)
| pKa =
| MagSus = -69.7·10<sup>−6</sup> cm<sup>3</sup>/mol
| Viscosity = 7.269 c] at 0 °C<br/>5.925 c] at 20 °C
}}
| Dipole =
|Section3={{Chembox Thermochemistry
}}
| DeltaHf = −39.9–−38.3 kJ mol<sup>−1</sup>
| Section7 = {{Chembox Hazards
| DeltaHc = −1.4629–−1.4621 MJ mol<sup>−1</sup>
| MainHazards = Possible teratogen. Possible risk of harm to the unborn child. Vesicant. Harmful by inhalation, ingestion and through skin contact. May cause sensitization. Narcotic.
| HeatCapacity = 109.7 J K<sup>−1</sup> mol<sup>−1</sup>
| FlashPt =
}}
| NFPA-H = 2
|Section4={{Chembox Hazards
| NFPA-F = 1
| GHSPictograms = {{GHS exclamation mark}} {{GHS health hazard}}
| NFPA-R = 1
| GHSSignalWord = '''DANGER'''
| NFPA-O =
| HPhrases = {{H-phrases|302|315|317|319|334|335}}
| RPhrases = {{R23}} {{R24}} {{R25}} {{R42}} {{R43}} {{R63}}
| PPhrases = {{P-phrases|261|280|305+351+338|342+311}}
| SPhrases = {{S45}} {{S26}} {{S36}} {{S37}} {{S39}} {{S23}}
| NFPA-H = 2
| ExternalMSDS =
| NFPA-F = 1
}}
| NFPA-R = 1
| Section8 = {{Chembox Related
| FlashPtC = 72
| Function = ]s
| LD50 = 330 g m<sup>−3</sup> <small>(oral, rat)</small>
| OtherFunctn = ]<br>]<br>]<br>]}}
}}
|Section5={{Chembox Related
| OtherFunction_label = iodoalkanes
| OtherFunction = {{Unbulleted list|]|]|]|]|]|]}}
| OtherCompounds = {{Unbulleted list|]|]|]}}
}}
}} }}


'''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. '''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.


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.
Ethyl iodide is very good with alkylation reactions. It is also used as the hydrogen radical promoter.


]{{clear left}}
==References==
{{reflist|1}}


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


==Production==
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.


: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>
{{organohalide-stub}}


The crude product is purified by distillation.
]

]
==References==
]
{{Reflist|1}}
]

]
{{Authority control}}
]

]
]
]