Ethyl iodide

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Ethyl iodide
Skeletal formula of ethyl iodide
Ball and stick model of ethyl iodide Spacefill model of ethyl iodide
CAS number 75-03-6 YesY
PubChem 6340
ChemSpider 6100 YesY
EC number 200-833-1
RTECS number KI4750000
Jmol-3D images Image 1
Molecular formula C2H5I
Molar mass 155.97 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
Solubility in water 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
Viscosity 5.925 mPa s (at 20 °C)
109.7 J K−1 mol−1
−39.9–−38.3 kJ mol−1
−1.4629–−1.4621 MJ mol−1
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H302, H315, H317, H319, H334, H335
P261, P280, P305+351+338, P342+311
EU classification Harmful Xn
R-phrases R20, R36/37/38, R42/43
S-phrases S23, S26, S36/37, S45
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 72 °C (162 °F; 345 K)
LD50 330 g m−3 (oral, rat)
Related compounds
Related iodoalkanes
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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. It may also be prepared by reaction between hydroiodic acid and ethanol distilling off the ethyl iodide. Ethyl iodide should be stored in copper powder to avoid fast decomposition, though even with this method samples don't 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.


Ethyl iodide is prepared by using red phosphorus, ethanol and iodine. There is absolute ethanol and iodine dust used in the process, which contains solving the phosphorus and iodine in the ethanol. During the process the temperature is controlled. The phosphorus triiodide is made in situ, due to the instability of it.[3]

\mathrm{3 \ C_2H_5OH + PI_3 \rightarrow 3 \ C_2H_5I + H_3PO_3}

The crude product is purified by distillation.


  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: Szerves Kémiai Praktikum page: 274, Eötvös kiadó 2012 ISBN 978-963-312-129-0