Ethyl iodide

Ethyl iodide
Names
IUPAC name
Iodoethane[1]
Identifiers
505934
75-03-6 Yes
ChEBI CHEBI:42487 
ChEMBL ChEMBL1232588 
ChemSpider 6100 Yes
EC number 200-833-1
Jmol-3D images Image
PubChem 6340
RTECS number KI4750000
Properties
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 °C; 160.6 °F; 344.6 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
1.513–1.514
Viscosity 5.925 mPa s (at 20 °C)
Thermochemistry
Specific
heat capacity (C)
 109.7 J K−1 mol−1
Std enthalpy of
formation (ΔfHo298)
 −39.9–−38.3 kJ mol−1
Std enthalpy of
combustion (ΔcHo298)
 −1.4629–−1.4621 MJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
H302, H315, H317, H319, H334, H335
P261, P280, P305+351+338, P342+311
EU classification 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
1
2
1
Flash point 72 °C (162 °F; 345 K)
330 g m−3 (oral, rat)
Related compounds
Related iodoalkanes
Related compounds
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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.

Production

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.

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