Ethyl iodide

Ethyl iodide

Names
IUPAC name Iodoethane[1]
Identifiers
CAS Number	75-03-6
Beilstein Reference	505934
ChEBI	CHEBI:42487
ChEMBL	ChEMBL1232588
ChemSpider	6100
EC Number	200-833-1
Jmol interactive 3D	Image
PubChem	6340
RTECS number	KI4750000
InChI InChI=1S/C2H5I/c1-2-3/h2H2,1H3 Key: HVTICUPFWKNHNG-UHFFFAOYSA-N
SMILES CCI
Properties
Chemical 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
Henry's law constant (kH)	1.8 μmol Pa^−1 kg^−1
Refractive index (nD)	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 (ΔfH^o298)	−39.9–−38.3 kJ mol^−1
Std enthalpy of combustion (ΔcH^o298)	−1.4629–−1.4621 MJ mol^−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H302, H315, H317, H319, H334, H335
GHS precautionary statements	P261, P280, P305+351+338, P342+311
EU classification (DSD)	Xn
R-phrases	R20, R36/37/38, R42/43
S-phrases	S23, S26, S36/37, S45
NFPA 704	1 2 1
Flash point	72 °C (162 °F; 345 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	330 g m^−3 (oral, rat)
Related compounds
Related iodoalkanes	Methyl iodide Diiodomethane Iodoform Carbon tetraiodide n-Propyl iodide Isopropyl iodide
Related compounds	Pimagedine Guanidine Diiodohydroxypropane
Except where otherwise noted, data are 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