| 词条 | 1,1-Diiodoethane |
| 释义 |
| ImageFile1 = 1,1-diiodoethane(1)(bond and stick model).png | ImageSize1 = 150 | ImageCaption1 = 1,1-diiodoethane(bond and stick model) | ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageFile2 = 1,1-diiodoethane(skeleton model).png | ImageSize2 = 100 | ImageCaption2 = 1,1-diiodoethane(skeleton model) | ImageFileL2_Ref = {{chemboximage|correct|??}} | ImageAlt = | IUPACName = 1,1-diiodoethane[1] | OtherNames = Ethylidene iodide | Section2 = {{Chembox Identifiers | EC_number = 209-821-0 | CASNo = 594-02-5 | CASNo_Ref = {{cascite|correct|CAS}} | SMILES = CC(I)I | PubChem= 68980 | ChemSpiderID = 62202 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | InChI = | InChIKey = | StdInChI = 1S/C2H4I2/c1-2(3)4/h2H,1H3 | StdInChI_Ref = {{stdinchicite|correct|PubChem}} | StdInChIKey = JNVXRQOSRUDXDY-UHFFFAOYSA-N}} | Section3 = {{Chembox Properties | C=2|H=4|I=2 | Appearance = | MolarMass = 281.863 g/mol | Density = 3.0±0.1 g/cm{{sup|3}}[2] | MeltingPtC = | BoilingPt = 154.7±23.0 °C | SolubleOther = most organic solvents}} | Section4 = {{Chembox Hazards | GHSPictograms = {{GHS06}} {{GHS07}} | GHSSignalWord = WARNING | PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|403+233|405|501}} | MainHazards = | FlashPt = 63.7±18.1 °C | AutoignitionPt = }} }} 1,1-Diiodoethane is an organic saturated haloalkane containing iodine with formula CH{{sub|3}}CHI{{sub|2}}. Preparation1,1-diiodoethane can be synthesized from gem-dihaloalkanes. The starting material is 1,1-dichloroethane, and iodoethane is a source of iodine. In the presence of aluminium trichloride, 1,1-dichloroethane will converted to 1,1-diiodoethane.[3] To be specific, mix 0.4 mol (~39.6 g) of 1,1-dichloroethane with 1.2 mol(~187 g) of ethyl iodide, and ~2.0 g of aluminum chloride. Heat for three hours using steam bath. Then, wash the mixture with H{{sub|2}}O and NaHSO{{sub|3}} respectively, and dry with MgSO{{sub|4}}. By boiling at 76-76 °C and 25 mmHg, about 67.3 g of product will be received when distilled.[4] The alternative method, which does not require 1,1-dichloroethane, is the reaction of iodine, triethylamine and hydrazone of acetaldehyde. Using 1 mol of acetaldehyde, about 95 g, which is 34% from acetaldehyde, of 1,1-diiodoethane formed.[4] Application1,1-diiodoethane is commonly used as a reactant in reaction such as SN2. The following are some examples of SN2 reaction using 1,1-diiodoethane as a reactant.[5] Moreover, is can also be used as a reactant in enolate substitution reaction as the following examples.[5] References1. ^{{Cite web|title=1,1-Diiodoethane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/compound/68980|work=PubChem Compound Database|publisher=National Center for Biotechnology Information|accessdate=7 June 2017|location=USA|at=Identification}} 2. ^{{Cite web|title=CSID:8014297|url=http://www.chemspider.com/Chemical-Structure.8014297.html|publisher=ChemSpider|accessdate=7 June 2017}} 3. ^1 {{cite book|last1=Benneche|first1=T.|last2=Challenger|first2=S.|last3=Chemla|first3=F.|last4=Cordier|first4=C.|last5=Demchenko|first5=A. V.|last6=De Meo|first6=C.|last7=Diaper|first7=C. M.|last8=Fascione|first8=M. A.|last9=Ferreira|first9=F.|last10=Gunn|first10=S. J.|last11=Kouklovsky|first11=C.|last12=Kryezka|first12=B.|last13=Leach|first13=S.|last14=Leroy|first14=B.|last15=Lewkowaki|first15=J.|last16=Ley|first16=S. V.|last17=Merino|first17=P.|last18=Milroy|first18=L.-G.|last19=Myers|first19=R. M.|last20=Nelson|first20=A.|last21=Oshima|first21=K.|last22=Rowlands|first22=G. J.|last23=Roy|first23=B.|last24=Stalford|first24=S. A.|last25=Turnbull|first25=W. B.|last26=Angerer|first26=S. von|last27=Warriner|first27=S. L.|last28=White|first28=J. W.|last29=Yorimitsu|first29=H.|last30=Zawisza|first30=A.|title=Science of Synthesis: Houben-Weyl Methods of Molecular Transformations|publisher=Thieme New York|date=2007|volume=29|pages=106|isbn=978-1-58890-461-4|url=https://books.google.com/?id=VSGGAwAAQBAJ&pg=PA106&lpg=PA106&dq=what+is+1,1-diiodoethane#v=onepage&q=1%2C1-diiodoethane&f=false|accessdate=8 June 2017}} 4. ^1 {{cite book|last1=Taschner|first1=Michael J.|title=e-EROS Encyclopedia of Reagents for Organic Synthesis|publisher=John Wiley & Sons|date=2001|doi=10.1002/047084289X.rd239|chapter=1,1-Diiodoethane|isbn=978-0471936237}} 5. ^1 2 3 4 5 "1,1-diiodoethane", Chemsink. Retrieved on 8 June 2017. External links
See also
1 : Iodoalkanes |
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