Ethyl iodide

Ethyl iodide (also iodoethane) is a colorless flammable chemical compound. It has the chemical formula C2H5I and is prepared by heating ethanol with iodine and phosphorus.[2] On contact with air, especially on the effect of light, it decomposes and turns yellow or reddish from dissolved iodine.

Ethyl iodide
Ball and stick model of ethyl iodide
Spacefill model of ethyl iodide
Names
IUPAC name
Iodoethane[1]
Identifiers
3D model (JSmol)
505934
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.758
EC Number
  • 200-833-1
RTECS number
  • KI4750000
UNII
Properties
C2H5I
Molar mass 155.966 g·mol−1
Appearance Colourless liquid
Density 1.940 g mL−1
Melting point −111.10 °C; −167.98 °F; 162.05 K
Boiling point 71.5 to 73.3 °C; 160.6 to 163.8 °F; 344.6 to 346.4 K
4 g L−1 (at 20 °C)
Solubility in ethanol Miscible
Solubility in diethyl ether Miscible
log P 2.119
Vapor pressure 17.7 kPa
1.8 μmol Pa−1 kg−1
-69.7·10−6 cm3/mol
1.513–1.514
Viscosity 5.925 mPa s (at 20 °C)
Thermochemistry
109.7 J K−1 mol−1
Std enthalpy of
formation (ΔfH⦵298)
 −39.9–−38.3 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −1.4629–−1.4621 MJ mol−1
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H302, H315, H317, H319, H334, H335
P261, P280, P305+351+338, P342+311
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
2
1
Flash point 72 °C (162 °F; 345 K)
Lethal dose or concentration (LD, LC):
330 g m−3 (oral, rat)
Related compounds
Related iodoalkanes
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

It may also be prepared by reaction between hydroiodic acid and ethanol distilling off the ethyl iodide. Ethyl iodide should be stored in the presence of copper powder to avoid rapid decomposition, though even with this method samples do not last more than 1 year.

Ethyl iodide distillation. It has a greenish color due to decomposition.

Because iodide is a good leaving group, ethyl iodide is an excellent ethylating agent. It is also used as the hydrogen radical promoter.

Production

Ethyl iodide is prepared by using red phosphorus, absolute ethanol and iodine. the iodine dissolve in the ethanol where it react with the solid phosphorus to form phosphorus triiodide, which must be formed in situ because it is unstable.[3] During the process the temperature is controlled.

C2H5OH + PI3 → 3 C2H5I + H3PO3

The crude product is purified by distillation.

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References
  1. "iodoethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 29 February 2012.
  2. Merck Index of Chemicals and Drugs, 9th ed., monograph 3753
  3. Csámpai, A; Láng, E; Majer, Zs; Orosz, Gy; Rábai, J; Ruff, F; Schlosser, G; Szabó, D; Vass, E (2012). Szerves Kémiai Praktikum. Eötvös kiadó. p. 274. ISBN 978-963-312-129-0.CS1 maint: multiple names: authors list (link)
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