1,1-Diiodoethane

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1,1-Diiodoethane
1,1-diiodoethane(1)(bond and stick model).png
1,1-diiodoethane(bond and stick model)
1,1-diiodoethane(skeleton model).png
1,1-diiodoethane(skeleton model)
Names
IUPAC name
1,1-diiodoethane[1]
Other names
Ethylidene iodide
Identifiers
3D model (JSmol)
ChemSpider
EC Number 209-821-0
Properties
C2H4I2
Molar mass 281.863 g/mol
Density 3.0±0.1 g/cm3[2]
Boiling point 154.7±23.0 °C
Solubility most organic solvents
Hazards
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
P261, P264, P270, P271, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313
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).
Infobox references

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

Preparation[edit]

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 aluminum 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[edit]

1,1-diiodoethane is commonly used as a reactant in reaction such as SN2. The following are some examples of SN2 reation 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]

References[edit]

  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. 29. Thieme New York. p. 106. ISBN 978-1-58890-461-4. Retrieved 8 June 2017. 
  4. ^ a b Taschner, Michael J. (2001). e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rd239. Retrieved 8 June 2017. 
  5. ^ a b c d e f "1,1-diiodoethane", Chemsink. Retrieved on 8 June 2017.

External links[edit]

See also[edit]