Iodoethane

Chemical properties

Colorless to yellow liquid. Iodoethane is a stable chemical substance. It is incompatible with strong bases, magnesium, and strong oxidising agents and gets discoloured when exposed to light, moisture, and air.

The Uses of Iodoethane

Iodoethane is an excellent ethylating agent used in organic synthesis to introduce an ethyl group into a compound. It reacts with magnesium to form the Grignard reagent, ethylmagnesium iodide which is used in organic synthesis. It is involved in the preparation of 1-ethyl-3-nitro-2-phenyl-indole and also serves as hydrogen radical promoter.

The Uses of Iodoethane

To a solution of the SM (40 g, 152.1 mmol) in DMF (400 mL) was added K2CO3 (63 g, 456 mmol) and EtI (24.3 mL, 304.2 mmol). The reaction mixture was stirred at RT for 16 h. The mixture was concentrated in vacuo, diluted with H2O (200 mL), and extracted with EtOAc (2 x 200 mL). The combined organics were washed with H2O (100 mL), dried (Na2SO4), and concentrated to provide the product as an off-white solid. [43 g, 95%]

The Uses of Iodoethane

A useful synthetic reagent for the introduction of ethyl groups

What are the applications of Application

Iodoethane is a useful synthetic reagent for the introduction of ethyl groups

Definition

ChEBI: An iodoalkane that is ethane substituted by an iodo group.

Definition

A colorless liquid alkyl halide made by reaction of ethanol with iodine in the presence of red phosphorus.

Synthesis Reference(s)

The Journal of Organic Chemistry, 12, p. 133, 1947 DOI: 10.1021/jo01165a017

General Description

Iodoethane also known as ethyl iodide is an alkyl iodide. The interaction of iodoethane with Pt(111) surfaces has been analyzed by using thermal desorption and X-ray photoelectron spectroscopy. Its microwave spectrum has been recorded and studied. The dynamics of the gas phase photolysis of iodoethane have been studied using resonance Raman spectra. Its thermodynamic characteristics in the ideal state have been reported.

Hazard

Toxic by inhalation and skin absorption, narcotic in high concentration.

Purification Methods

Drying the iodide with P2O5 is unsatisfactory, and with CaCl2 it is incomplete. It is probably best to dry it with sodium wire and distil [Hammond et al. J Am Chem Soc 82 704 1960]. Exposure of ethyl iodide to light leads to rapid decomposition, with the liberation of iodine. Free iodine can be removed by shaking with several portions of dilute aqueous Na2S2O3 (until the colour is discharged), followed by washing with water, drying (with CaCl2, then sodium), and distilling. The distilled ethyl iodide is stored, over mercury, in a dark bottle away from direct sunlight. Other purification procedures include passage through a 60cm column of silica gel, followed by distillation, and treatment with elemental bromine, extraction of free halogen with Na2S2O3 solution, followed by washing with water, drying and distilling. Free iodine and HI have also been removed by direct distillation through a LeBel-Henninger column containing copper turnings. Purification by shaking with alkaline solutions, and storage over silver, are reported to be unsatisfactory. [Beilstein 1 IV 163.]