1,1-Diiodoethane

1,1-Diiodoethane
Skeletal model
Ball and stick model
Names
Preferred IUPAC name
1,1-Diiodoethane[1]
Other names
Ethylidene iodide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.930 Edit this at Wikidata
EC Number
  • 209-821-0
  • InChI=1S/C2H4I2/c1-2(3)4/h2H,1H3 checkY[PubChem]
    Key: JNVXRQOSRUDXDY-UHFFFAOYSA-N
  • CC(I)I
Properties
C2H4I2
Molar mass 281.863 g·mol−1
Density 3.0±0.1 g/cm3[2]
Boiling point 154.7±23.0 °C
Solubility most organic solvents
Hazards
GHS labelling:
GHS06: Toxic GHS07: Exclamation mark
Warning
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 63.7±18.1 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,1-Diiodoethane is an organic saturated haloalkane containing iodine with formula CH3CHI2.

Preparation

1,1-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]

The preparation of 1,1-diiodoethane from gem-dihaloalkanes.
The preparation of 1,1-diiodoethane from gem-dihaloalkanes[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 aluminium chloride. Heat for three hours using steam bath. Then, wash the mixture with H2O and NaHSO3 respectively, and dry with MgSO4. 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]

Application

1,1-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]

Preparation of 1-iodoethyl cyclohexanecarboxylate[5]
Preparation of 1-iodoethyl (2-methylbutyl) carbonate[5]

Moreover, is can also be used as a reactant in enolate substitution reaction as the following examples.[5]

Preparation of 3-iodo-N,N-diisopropyl-2-methylbutanamide[5]
Preparation of 3-iodo-1-(pyrrolidin-1-yl)butan-1-one[5]

See also

References

  1. ^ "1,1-Diiodoethane - Compound Summary". PubChem Compound Database. USA: National Center for Biotechnology Information. Identification. Retrieved 7 June 2017.
  2. ^ "CSID:8014297". ChemSpider. Retrieved 7 June 2017.
  3. ^ a b Benneche, T.; Challenger, S.; Chemla, F.; Cordier, C.; Demchenko, A. V.; De Meo, C.; Diaper, C. M.; Fascione, M. A.; Ferreira, F.; Gunn, S. J.; Kouklovsky, C.; Kryezka, B.; Leach, S.; Leroy, B.; Lewkowaki, J.; Ley, S. V.; Merino, P.; Milroy, L.-G.; Myers, R. M.; Nelson, A.; Oshima, K.; Rowlands, G. J.; Roy, B.; Stalford, S. A.; Turnbull, W. B.; Angerer, S. von; Warriner, S. L.; White, J. W.; Yorimitsu, H.; Zawisza, A. (2007). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Vol. 29. Thieme New York. p. 106. ISBN 978-1-58890-461-4. Retrieved 8 June 2017.
  4. ^ a b Taschner, Michael J. (2001). "1,1-Diiodoethane". e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rd239. ISBN 978-0471936237.
  5. ^ a b c d e f "1,1-diiodoethane", Chemsink. Retrieved on 8 June 2017.