1,2-Diiodoethane

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

1,2-Diiodoethane
Skeletal formula of 1,2-diiodoethane
Skeletal formula of 1,2-diiodoethane
Stick and Balls model of 1,2-diiodoethane
Stick and Balls model of 1,2-diiodoethane
Tube model of 1,2-diiodoethane
Tube model of 1,2-diiodoethane
Space Filling model of 1,2-diiodoethane
Space Filling model of 1,2-diiodoethane
Names
Preferred IUPAC name
1,2-Diiodoethane
Other names
Ethylene iodide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.872
UNII
  • 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
  • ICCI
Properties
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

Preparation and reactions

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

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).

References
  1. Buckingham, John (1990). Dictionary of Organic Compounds. Vol. 7. CRC Press. p. 2495. ISBN 9780412540905. Retrieved 5 January 2014.
  2. 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.
  3. 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.
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