Ethyl iodide

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Ethyl iodide
Iodoethane FormulaV1.svg
Ball and stick model of ethyl iodide Iodoethane-3D-balls.png
Ball and stick model of ethyl iodide
Spacefill model of ethyl iodide EthylIodide.png
Spacefill model of ethyl iodide
Names
Preferred IUPAC name
Iodoethane [1]
Identifiers
3D model (JSmol)
505934
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.758 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-833-1
PubChem CID
RTECS number
  • KI4750000
UNII
  • InChI=1S/C2H5I/c1-2-3/h2H2,1H3 Yes check.svgY
    Key: HVTICUPFWKNHNG-UHFFFAOYSA-N Yes check.svgY
  • CCI
Properties
C2H5I
Molar mass 155.966 g·mol−1
AppearanceColourless 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
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
1.8 μmol Pa−1 kg−1
-69.7·10−6 cm3/mol
1.513–1.514
Viscosity 5.925 mPa s (at 20 °C)
Thermochemistry
109.7 J K−1 mol−1
−39.9–−38.3 kJ mol−1
−1.4629–−1.4621 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H302, H315, H317, H319, H334, H335
P261, P280, P305+P351+P338, P342+P311
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
1
1
Flash point 72 °C (162 °F; 345 K)
Lethal dose or concentration (LD, LC):
330 g m−3(oral, rat)
Related compounds
Related iodoalkanes
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. Ethyl Iodide production.jpg
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.

Related Research Articles

<span class="mw-page-title-main">Iodine</span> Chemical element, symbol I and atomic number 53

Iodine is a chemical element; it has symbol I and atomic number 53. The heaviest of the stable halogens, it exists at standard conditions as a semi-lustrous, non-metallic solid that melts to form a deep violet liquid at 114 °C (237 °F), and boils to a violet gas at 184 °C (363 °F). The element was discovered by the French chemist Bernard Courtois in 1811 and was named two years later by Joseph Louis Gay-Lussac, after the Ancient Greek Ιώδης, meaning 'violet'.

<span class="mw-page-title-main">Silver fulminate</span> High explosive used in bang snaps

Silver fulminate (AgCNO) is the highly explosive silver salt of fulminic acid.

<span class="mw-page-title-main">Hydrogen iodide</span> Chemical compound

Hydrogen iodide (HI) is a diatomic molecule and hydrogen halide. Aqueous solutions of HI are known as hydroiodic acid or hydriodic acid, a strong acid. Hydrogen iodide and hydroiodic acid are, however, different in that the former is a gas under standard conditions, whereas the other is an aqueous solution of the gas. They are interconvertible. HI is used in organic and inorganic synthesis as one of the primary sources of iodine and as a reducing agent.

Cyanogen iodide or iodine cyanide (ICN) is a pseudohalogen composed of iodine and the cyanide group. It is a highly toxic inorganic compound. It occurs as white crystals that react slowly with water to form hydrogen cyanide.

<span class="mw-page-title-main">Ammonium iodide</span> Chemical compound

Ammonium iodide is the inorganic compound with the formula NH4I. A white solid. It is an ionic compound, although impure samples appear yellow. This salt consists of ammonium cation and an iodide anion. It can be prepared by the action of hydroiodic acid on ammonia. It is easily soluble in water, from which it crystallizes in cubes. It is also soluble in ethanol. Ammonium iodide in aqueous solutions are observed as acidic and display elevated vapor pressures at high temperatures

Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.

Iodometry, known as iodometric titration, is a method of volumetric chemical analysis, a redox titration where the appearance or disappearance of elementary iodine indicates the end point.

Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odor.

<span class="mw-page-title-main">Nickel(II) iodide</span> Chemical compound

Nickel(II) iodide is an inorganic compound with the formula NiI2. This paramagnetic black solid dissolves readily in water to give bluish-green solutions, from which crystallizes the aquo complex [Ni(H2O)6]I2 (image above). This bluish-green colour is typical of hydrated nickel(II) compounds. Nickel iodides find some applications in homogeneous catalysis.

<span class="mw-page-title-main">Diiodomethane</span> Chemical compound

Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a very dense colorless liquid; however, it decomposes upon exposure to light liberating iodine, which colours samples brownish. It is slightly soluble in water, but soluble in organic solvents. It has a very high refractive index of 1.741, and a surface tension of 0.0508 N·m−1.

<span class="mw-page-title-main">Triethyl phosphite</span> Chemical compound

Triethyl phosphite is an organophosphorus compound, specifically a phosphite ester, with the formula P(OCH2CH3)3, often abbreviated P(OEt)3. It is a colorless, malodorous liquid. It is used as a ligand in organometallic chemistry and as a reagent in organic synthesis.

<span class="mw-page-title-main">Magnesium iodide</span> Chemical compound

Magnesium iodide is an inorganic compound with the chemical formula MgI2. It forms various hydrates MgI2·xH2O. Magnesium iodide is a salt of magnesium and hydrogen iodide. These salts are typical ionic halides, being highly soluble in water.

<span class="mw-page-title-main">Beryllium iodide</span> Chemical compound

Beryllium iodide is the inorganic compound with the formula BeI2. It is a hygroscopic white solid.

<span class="mw-page-title-main">Isopropyl iodide</span> Chemical compound

Isopropyl iodide is the organoiodine compound with the formula (CH3)2CHI. It is colorless, flammable, and volatile. Organic iodides are light-sensitive and take on a yellow colour upon storage, owing to the formation of iodine.

<span class="mw-page-title-main">Sodium ethyl xanthate</span> Chemical compound

Sodium ethyl xanthate (SEX) is an organosulfur compound with the chemical formula CH3CH2OCS2Na. It is a pale yellow powder, which is usually obtained as the dihydrate. Sodium ethyl xanthate is used in the mining industry as a flotation agent. A closely related potassium ethyl xanthate (KEX) is obtained as the anhydrous salt.

Iron(II) iodide is an inorganic compound with the chemical formula FeI2. It is used as a catalyst in organic reactions.

<span class="mw-page-title-main">Allyl iodide</span> Chemical compound

Allyl iodide (3-iodopropene) is an organic halide used in synthesis of other organic compounds such as N-alkyl-2-pyrrolidones, sorbic acid esters, 5,5-disubstituted barbituric acids, and organometallic catalysts. Allyl iodide can be synthesized from allyl alcohol and methyl iodide on triphenyl phosphite, Finkelstein reaction on allyl halides, or by the action of elemental phosphorus and iodine on glycerol. Allyl iodide dissolved in hexane can be stored for up to three months in a dark freezer at −5 °C (23 °F) before decomposition into free iodine becomes apparent.

Samarium(III) iodide is an inorganic compound, a salt of samarium and hydroiodic acid with the chemical formula SmI
3
.

Europium(III) iodide is an inorganic compound containing europium and iodine with the chemical formula EuI3.

<span class="mw-page-title-main">Platinum(IV) iodide</span> Chemical compound

Platinum(IV) iodide is a inorganic compound with the formula PtI4. it is a dark brown diamagnetic solid and is one of several binary iodides of platinum.

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 (2012). Szerves Kémiai Praktikum. Eötvös kiadó. p. 274. ISBN   978-963-312-129-0.