Isopropyl iodide

Last updated
Isopropyl iodide
Isopropyl iodide stick.png
IsopropylIodide.png
Names
Preferred IUPAC name
2-Iodopropane [1]
Identifiers
3D model (JSmol)
1098244
ChemSpider
ECHA InfoCard 100.000.782 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-859-3
MeSH isopropyl+iodide
PubChem CID
RTECS number
  • TZ4200000
UNII
UN number 2392
  • InChI=1S/C3H7I/c1-3(2)4/h3H,1-2H3 X mark.svgN
    Key: FMKOJHQHASLBPH-UHFFFAOYSA-N Yes check.svgY
  • CC(C)I
Properties
C3H7I
Molar mass 169.993 g·mol−1
AppearanceColourless liquid
Density 1.703 g mL−1
Melting point −90.00 °C; −130.00 °F; 183.15 K
Boiling point 88.8 to 89.8 °C; 191.7 to 193.5 °F; 361.9 to 362.9 K
1.4 g L−1 (at 12.5 °C)
Solubility in chloroform Miscible
Solubility in ethanol Miscible
Solubility in diethyl ether Miscible
Solubility in benzene Miscible
890 nmol Pa−1 kg−1
1.4997
Viscosity 6.971 mPa (at 20 °C)
Thermochemistry
137.3 J K−1 mol−1
−77.2–−72.6 kJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H226, H302
Flash point 42 °C (108 °F; 315 K)
Related compounds
Related alkanes
Related compounds
Diiodohydroxypropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Preparation

Isopropyl iodide is prepared by iodination of isopropyl alcohol using hydrogen iodide or, equivalently, with a mixture of glycerol, iodine, and phosphorus. [2] An alternative preparation involves the reaction of 2-propyl bromide with an acetone solution of sodium iodide (Finkelstein reaction): [3]

(CH3)2CHBr + NaI → (CH3)2CHI + NaBr

Related Research Articles

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

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'.

<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

Iodoform Chemical compound

Iodoform (also known as triiodomethane and, inaccurately, as carbon triiodide) is the organoiodine compound with the chemical formula CHI3. A pale yellow, crystalline, volatile substance, it has a penetrating and distinctive odor (in older chemistry texts, the smell is sometimes referred to as that of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.

In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens (F2, Cl2, Br2, I2). Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride.

Phosphorus triiodide Chemical compound

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 Chemical compound

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.

Sodium iodide Chemical compound

Sodium iodide (chemical formula NaI) is an ionic compound formed from the chemical reaction of sodium metal and iodine. Under standard conditions, it is a white, water-soluble solid comprising a 1:1 mix of sodium cations (Na+) and iodide anions (I) in a crystal lattice. It is used mainly as a nutritional supplement and in organic chemistry. It is produced industrially as the salt formed when acidic iodides react with sodium hydroxide. It is a chaotropic salt.

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.

Triiodide Ion

In chemistry, triiodide usually refers to the triiodide ion, I
3
. This anion, one of the polyhalogen ions, is composed of three iodine atoms. It is formed by combining aqueous solutions of iodide salts and iodine. Some salts of the anion have been isolated, including thallium(I) triiodide (Tl+[I3]) and ammonium triiodide ([NH4]+[I3]). Triiodide is observed to be a red colour in solution.

Lithium iodide Chemical compound

Lithium iodide, or LiI, is a compound of lithium and iodine. When exposed to air, it becomes yellow in color, due to the oxidation of iodide to iodine. It crystallizes in the NaCl motif. It can participate in various hydrates.

Copper(I) iodide Chemical compound

Copper(I) iodide is the inorganic compound with the formula CuI. It is also known as cuprous iodide. It is useful in a variety of applications ranging from organic synthesis to cloud seeding.

Hydrazone iodination

Hydrazone iodination is an organic reaction in which a hydrazone is converted into a vinyl iodide by reaction of iodine and a non-nucleophilic base such as DBU. First published by Derek Barton in 1962 the reaction is sometimes referred to as the Barton reaction or, more descriptively, as the Barton vinyl iodine procedure.

Aluminium iodide Chemical compound

Aluminium iodide is a chemical compound containing aluminium and iodine. Invariably, the name refers to a compound of the composition AlI
3
, formed by the reaction of aluminium and iodine or the action of HI on Al metal. The hexahydrate is obtained from a reaction between metallic aluminum or aluminum hydroxide with hydrogen iodide or hydroiodic acid. Like the related chloride and bromide, AlI
3
is a strong Lewis acid and will absorb water from the atmosphere. It is employed as a reagent for the scission of certain kinds of C-O and N-O bonds. It cleaves aryl ethers and deoxygenates epoxides.

Iodine monochloride Chemical compound

Iodine monochloride is an interhalogen compound with the formula ICl. It is a red-brown chemical compound that melts near room temperature. Because of the difference in the electronegativity of iodine and chlorine, this molecule is highly polar and behaves as a source of I+.

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

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.

Organoiodine compounds are organic compounds that contain one or more carbon–iodine bonds. They occur widely in organic chemistry, but are relatively rare in nature. The thyroxine hormones are organoiodine compounds that are required for health and the reason for government-mandated iodization of salt.

Iodane generally refers to any organic derivative of iodine. Without modifier, iodane is the systematic name for the parent hydride of iodine, HI. Thus, any organoiodine compound with general formula RI is a substituted iodane. However, as used in the context of organic synthesis, the term iodane more specifically refers to organoiodine compounds with nonstandard bond number, making this term a synonym for hypervalent iodine. These iodine compounds are hypervalent because the iodine atom formally contains more than the 8 electrons in the valence shell required for the octet rule. When iodine is ligated to an organic residue and electronegative ligands, hypervalent iodine compounds occur with a +3 oxidation number as iodine(III) or λ3-iodanes, or as a +5 oxidation number as iodine(V) or λ5-iodanes, or as a +7 oxidation number as iodine(VII) or λ7-iodanes.

1,2-Diiodoethane Chemical compound

1,2-Diiodoethane is an organoiodine compound.

1,1-Diiodoethane is an organic saturated haloalkane containing iodine with formula CH3CHI2.

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

References

  1. "isopropyl iodide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 3 March 2012.
  2. Merck Index of Chemicals and Drugs, 9th ed., monograph 5074
  3. Textbook of Practical Organic Chemistry, 5th Edition, Prentice Hall, 1989