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
	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;
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 C(CI)I;
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

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).

gollark: (also I may eventually want to use ARM)

gollark: On the one hand I do somewhat want to run osmarksforum™ with this for funlolz, but on the other hand handwritten ASM is probably not secure.

gollark: > Well, the answer is a good cause for flame war, but I will risk. ;) At first, I find assembly language much more readable than HLL languages and especially C-like languages with their weird syntax. > At second, all my tests show, that in real-life applications assembly language always gives at least 200% performance boost. The problem is not the quality of the compilers. It is because the humans write programs in assembly language very different than programs in HLL. Notice, that you can write HLL program as fast as an assembly language program, but you will end with very, very unreadable and hard for support code. In the same time, the assembly version will be pretty readable and easy for support. > The performance is especially important for server applications, because the program runs on hired hardware and you are paying for every second CPU time and every byte RAM. AsmBB for example can run on very cheap shared web hosting and still to serve hundreds of users simultaneously.

gollark: https://board.asm32.info/asmbb/asmbb-v2-9-has-been-released.328/

gollark: Huh, apparently some hugely apioformic entity wrote a bit of forum software entirely in assembly.

References

Buckingham, John (1990). Dictionary of Organic Compounds. 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.

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[CRC_Press_-_Dictionary_of_Organic_Compounds-1] Buckingham, John (1990). Dictionary of Organic Compounds. 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.