1,2-Diiodoethane

1,2-Diiodoethane
Skeletal formula of 1,2-diiodoethane	Stick and Balls model of 1,2-diiodoethane
Tube model of 1,2-diiodoethane	Space Filling model of 1,2-diiodoethane
Names
	Preferred IUPAC name 1,2-Diiodoethane
	Other names Ethylene iodide
Identifiers
CAS Number	624-73-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	11723;
ECHA InfoCard	100.009.872
PubChem CID	12224;
UNII	9YH8PPH966 ;
CompTox Dashboard (EPA)	DTXSID8060791 ;
	InChI InChI=1S/C2H4I2/c3-1-2-4/h1-2H2 Key: GBBZLMLLFVFKJM-UHFFFAOYSA-N; InChI=1/C2H4I2/c3-1-2-4/h1-2H2 Key: GBBZLMLLFVFKJM-UHFFFAOYAR;
	SMILES ICCI;
Properties
Chemical formula	C2H4I2
Molar mass	281.863 g·mol−1
Density	2.13 g/cm3
Melting point	80 to 82 °C (176 to 180 °F; 353 to 355 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,2-Diiodoethane is an organoiodine compound.^[1]

Preparation and reactions edit

1,2-Diiodoethane can be prepared by the reaction of ethylene with iodine (I₂):^[2]

C₂H₄ + I₂ ⇌ C₂H₄I₂

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.^[3]

Sm + ICH₂CH₂I → SmI₂ + H₂C=CH₂

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).

^ Buckingham, John (1990). Dictionary of Organic Compounds. Vol. 7. CRC Press. p. 2495. ISBN 9780412540905. Retrieved 5 January 2014.
^ Cutherbertson, G.R.; Kistiakowsky, G.B. (1935). "The thermal equilibrium between ethylene iodide, ethylene and iodine". J. Chem. Phys. 3 (10): 631–634. Bibcode:1935JChPh...3..631C. doi:10.1063/1.1749566.
^ Girard, P.; Namy, J. L.; Kagan, H. B. (1980). "Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents". Journal of the American Chemical Society. 102 (8): 2693–2698. doi:10.1021/ja00528a029.