Names | |||
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Preferred IUPAC name Iodoethane [1] | |||
Identifiers | |||
3D model (JSmol) | |||
505934 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.000.758 | ||
EC Number |
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PubChem CID | |||
RTECS number |
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UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
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 | ||
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 | ||
-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: | |||
Danger | |||
H302, H315, H317, H319, H334, H335 | |||
P261, P280, P305+P351+P338, P342+P311 | |||
NFPA 704 (fire diamond) | |||
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 | |||
Related compounds | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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.
Because iodide is a good leaving group, ethyl iodide is an excellent ethylating agent. It is also used as the hydrogen radical promoter.
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.
The crude product is purified by distillation.
Ethanol is an organic compound. It is a simple alcohol with the chemical formula C2H6O. Its formula can be also written as CH3−CH2−OH or C2H5OH. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, the active ingredient in alcoholic drinks.
Iodine is a chemical element with the symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions 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 'violet-coloured'.
Nitrogen triiodide is an inorganic compound with the formula NI3. It is an extremely sensitive contact explosive: small quantities explode with a loud, sharp snap when touched even lightly, releasing a purple cloud of iodine vapor; it can even be detonated by alpha radiation. NI3 has a complex structural chemistry that is difficult to study because of the instability of the derivatives. Although nitrogen is more electronegative than iodine, the compound was so named due to its analogy to the compound nitrogen trichloride.
Silver fulminate (AgCNO) is the highly explosive silver salt of fulminic acid.
Phosphorus triiodide (PI3) is an inorganic compound with the formula PI3. A red solid, it is a common misconception that PI3 is too unstable to be stored; it is, in fact, commercially available. It is widely used in organic chemistry for converting alcohols to alkyl iodides. It is also a powerful reducing agent. Note that phosphorus also forms a lower iodide, P2I4, but the existence of PI5 is doubtful at room temperature.
Hydrogen iodide 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.
Ammonium iodide is the chemical compound NH4I. It is used in photographic chemicals and some medications. 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. It gradually turns yellow on standing in moist air, owing to decomposition with liberation of iodine.
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.
Iodine heptafluoride, also known as iodine(VII) fluoride or iodine fluoride, is an interhalogen compound with the chemical formula IF7. It has an unusual pentagonal bipyramidal structure, as predicted by VSEPR theory. The molecule can undergo a pseudorotational rearrangement called the Bartell mechanism, which is like the Berry mechanism but for a heptacoordinated system. It forms colourless crystals, which melt at 4.5 °C: the liquid range is extremely narrow, with the boiling point at 4.77 °C. The dense vapor has a mouldy, acrid odour. The molecule has D5h symmetry.
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.
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.
Iodine can form compounds using multiple oxidation states. Iodine is quite reactive, but it is much less reactive than the other halogens. For example, while chlorine gas will halogenate carbon monoxide, nitric oxide, and sulfur dioxide, iodine will not do so. Furthermore, iodination of metals tends to result in lower oxidation states than chlorination or bromination; for example, rhenium metal reacts with chlorine to form rhenium hexachloride, but with bromine it forms only rhenium pentabromide and iodine can achieve only rhenium tetraiodide. By the same token, however, since iodine has the lowest ionisation energy among the halogens and is the most easily oxidised of them, it has a more significant cationic chemistry and its higher oxidation states are rather more stable than those of bromine and chlorine, for example in iodine heptafluoride.
Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a 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 relatively high refractive index of 1.741, and a surface tension of 0.0508 N·m−1.
Magnesium iodide is the name for the chemical compounds with the formulas MgI2 and its various hydrates MgI2(H2O)x. These salts are typical ionic halides, being highly soluble in water.
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.
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.
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.
Europium(III) iodide is an inorganic compound containing europium and iodine with the chemical formula EuI3.