:1,2-Diiodoethane
{{Course assignment | course = Education Program:Mahidol University International College/ICCH336 (2016-17T3) | term = Spring 2015}}
{{Chembox
| ImageFileL1 = Diiodoethane.svg
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Skeletal formula of 1,2-diiodoethane
| ImageSizeL1=150
| ImageFileR1 = Sticks and balls model of 1,2-Diiodoethane.png
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Stick and Balls model of 1,2-diiodoethane
| ImageSizeR1=150
| ImageFileL2 = Tube model of 1,2-Diiodoethane.png
| ImageFileL2_Ref = {{chemboximage|correct|??}}
| ImageNameL2 = Tube model of 1,2-diiodoethane
| ImageSizeL2=150
| ImageFileR2 =Spacefilling model of 1,2-Diiodoethane.png
| ImageFileR2_Ref = {{chemboximage|correct|??}}
| ImageNameR2 = Space Filling model of 1,2-diiodoethane
| ImageSizeR2=150
| PIN = 1,2-Diiodoethane
| OtherNames = Ethylene iodide
| Section1 = {{Chembox Identifiers
| CASNo = 624-73-7
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9YH8PPH966
| SMILES = ICCI
| PubChem = 12224
| ChemSpiderID = 11723
| InChI = 1/C2H4I2/c3-1-2-4/h1-2H2
| InChIKey = GBBZLMLLFVFKJM-UHFFFAOYAR
| StdInChI = 1S/C2H4I2/c3-1-2-4/h1-2H2
| StdInChIKey = GBBZLMLLFVFKJM-UHFFFAOYSA-N}}
| Section2 = {{Chembox Properties
| C=2|H=4|I=2
| Appearance =
| Density = 2.13 g/cm{{sup|3}}
| MeltingPtC = 80 to 82
| BoilingPt =
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
1,2-Diiodoethane is an organoiodine compound.{{cite book|last=Buckingham|first=John |title=Dictionary of Organic Compounds|publisher=CRC Press|date=1990|volume=7|pages=2495|isbn=9780412540905|url=https://books.google.com/books?id=C3Uo1co4Wv0C&dq=%22diiodoethane%22&pg=PA2495|accessdate=5 January 2014}}
Preparation and reactions
1,2-Diiodoethane can be prepared by the reaction of ethylene with iodine (I{{sub|2}}):{{cite journal |author=Cutherbertson, G.R. |author2=Kistiakowsky, G.B. | title = The thermal equilibrium between ethylene iodide, ethylene and iodine | journal = J. Chem. Phys. | date = 1935 | volume = 3 | issue = 10 | pages = 631–634| doi = 10.1063/1.1749566 | bibcode = 1935JChPh...3..631C }}
:C{{sub|2}}H{{sub|4}} + I{{sub|2}} {{eqm}} C{{sub|2}}H{{sub|4}}I{{sub|2}}
1,2-Diiodoethane is most commonly used in organic synthesis in the preparation of samarium(II) iodide or ytterbium(II) iodide in an inert solvent such as THF.{{Cite journal | doi = 10.1021/ja00528a029| title = Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents| journal = Journal of the American Chemical Society| volume = 102| issue = 8| pages = 2693–2698| year = 1980| last1 = Girard| first1 = P.| last2 = Namy| first2 = J. L.| last3 = Kagan| first3 = H. B.}}
:Sm + ICH2CH2I → SmI2 + H2C=CH2
Spectral properties
In mass spectroscopy, 1,2-diiodoethane exhibits 5 major peaks, with the base peak showing at 155 m/z, which is the loss of one iodine atom (127 m/z).