Ethyl iodide
| Names | |
|---|---|
| IUPAC name
Iodoethane
| |
| Other names
1-Ethyl iodide
Ethyl iodine Iodo-ethane Monoiodoethane | |
| Identifiers | |
| Jmol-3D images | Image |
| |
| Properties | |
| 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)[1] |
| 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) |
| 0.4 g/100 ml (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 Propyl 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.
Contents
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
- ↑ Kibardin, A.M.; Gryaznov, P.I.; Gazizov, T.Kh.; Pudovik, A.N.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2166 - 2168
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- Chemical compounds
- Organic compounds
- Organoiodine compounds
- Haloalkanes
- Volatile chemicals
- Carcinogenic
- Liquids
