Ethyl iodide

Ethyl iodide

Names
IUPAC name Iodoethane
Other names 1-Ethyl iodide Ethyl iodine Iodo-ethane Monoiodoethane
Identifiers
Jmol-3D images	Image
SMILES CCI
Properties
Chemical formula	CH3CH2I
Molar mass	155.97 g/mol
Appearance	Colorless liquid Brownish liquid (old sample)
Odor	Pungent, ether-like
Density	1.9308 g/cm3 (at 20 °C)
Melting point	−111.10 °C (−167.98 °F; 162.05 K)
Boiling point	71.5 to 73.3 °C (160.7 to 163.9 °F; 344.6 to 346.4 K)
Solubility in water	4 g/L (at 20 °C)
Solubility	Miscible with alcohol, diethyl ether
Vapor pressure	17.7 kPa
Viscosity	5.925 mPa s (at 20 °C)
Hazards
Safety data sheet	ScienceLab
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	330 mg/kg (rat, oral)
Related compounds
Related compounds	Methyl iodide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ethyl iodide or iodoethane is an organic chemical compound of iodine, which appears as a colorless dense liquid (older samples have a brownish or yellowish color), insoluble in water but miscible with other solvents. It has the chemical formula CH₃CH₂I, sometimes written as EtI.

Properties

Chemical

Like most alkyl iodides, ethyl iodide hydrolyzes in the presence of an alkali:

CH₃CH₂I + MOH → CH₃CH₂OH + MI

Physical

Ethyl iodide is a dense, colorless (though old samples have a brownish color) liquid, immiscible in water, but miscible with many solvents such as diethyl ether, ethanol, methanol. Ethyl iodide is toxic and has a strong ether-like odor. It has a density of 1.9308 g/cm³ at 20 °C.

Availability

Ethyl iodide is sold by various chemical suppliers, though it's difficult to acquire by the amateur chemist.

Preparation

Ethyl iodide can be prepared by distilling off a mixture of anhydrous ethanol with hydroiodic acid or hydrogen iodide.

A more direct route involves anhydrous ethanol, red phosphorus and iodine. Phosphorus and iodine react forming the unstable phosphorus triiodide, which reacts with ethanol to yield iodoethane:

3 CH₃CH₂OH + PI₃ → 3 CH₃CH₂I + H₃PO₃

Projects

• Make esters
• Diethyl zinc synthesis

Handling

Safety

Ethyl iodide is toxic and carcinogenic.

Iodoethane MUST be kept away from heavy metals as it reacts to form extremely toxic heavy ethyl iodides, which are more toxic than their corresponding metals. AVOID contact with their amalgam, as this yields their volatile, extremely toxic and quite deadly organometallic derivatives.

Storage

Ethyl iodide must be stored in amber bottles, in dark well ventilated places, away from light. Copper or silver wire can be added as a stabilizer.

Disposal

Ethyl iodide can be hydrolyzed to ethanol with sodium hydroxide, which can be either burned or recycled if necessary.

References

Relevant Sciencemadness threads

• Ethyl Iodide