Ethyl iodide

Ethyl iodide
Ball and stick model of ethyl iodide	Spacefill model of ethyl iodide
Names
	Preferred IUPAC name Iodoethane[1]
Identifiers
CAS Number	75-03-6 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	505934
ChEBI	CHEBI:42487 ;
ChEMBL	ChEMBL1232588 ;
ChemSpider	6100 ;
ECHA InfoCard	100.000.758
EC Number	200-833-1;
PubChem CID	6340;
RTECS number	KI4750000;
UNII	59PO05D39L ;
CompTox Dashboard (EPA)	DTXSID9058783 ;
	InChI InChI=1S/C2H5I/c1-2-3/h2H2,1H3 Key: HVTICUPFWKNHNG-UHFFFAOYSA-N ;
	SMILES CCI;
Properties
Chemical formula	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
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
Magnetic susceptibility (χ)	-69.7·10−6 cm3/mol
Refractive index (nD)	1.513–1.514
Viscosity	5.925 mPa s (at 20 °C)
Thermochemistry
Heat capacity (C)	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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H317, H319, H334, H335
Precautionary statements	P261, P280, P305+P351+P338, P342+P311
NFPA 704 (fire diamond)	2 1 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). verify (what is ?) 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 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 dissolves in the ethanol, where it reacts with the solid phosphorus to form phosphorus triiodide.[3] During this process, the temperature is controlled.

3 C₂H₅OH + PI₃ → 3 C₂H₅I + H₃PO₃

The crude product is purified by distillation.

References

"iodoethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 29 February 2012.
Merck Index of Chemicals and Drugs, 9th ed., monograph 3753
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.

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[1] "iodoethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 29 February 2012.

[merck-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.