Isopropyl Iodide
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Isopropyl iodide is the
organoiodine compound Organoiodine chemistry is the study of the synthesis and properties of organoiodine compounds, or organoiodides, organic compounds that contain one or more carbon–iodine bonds. They occur widely in organic chemistry, but are relatively rare ...
with the
formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
(CH3)2CHI. It is colorless,
flammable A combustible material is a material that can burn (i.e., sustain a flame) in air under certain conditions. A material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort ...
, and volatile. Organic iodides are light-sensitive and take on a yellow colour upon storage, owing to the formation of
iodine 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 , and boils to a vi ...
.


Preparation

Isopropyl iodide is prepared by iodination of
isopropyl alcohol Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable, organic compound with a pungent alcoholic odor. Isopropyl alcohol, an organic polar molecule, is miscible in water, ethanol, an ...
using
hydrogen iodide 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 und ...
or, equivalently, with a mixture of
glycerol Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...
,
iodine 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 , and boils to a vi ...
, and
phosphorus Phosphorus is a chemical element; it has Chemical symbol, symbol P and atomic number 15. All elemental forms of phosphorus are highly Reactivity (chemistry), reactive and are therefore never found in nature. They can nevertheless be prepared ar ...
.Merck Index of Chemicals and Drugs, 9th ed., monograph 5074 An alternative preparation involves the reaction of 2-propyl bromide with an acetone solution of
sodium iodide 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 ...
(
Finkelstein reaction The Finkelstein reaction, named after the German chemist Hans Finkelstein, is a type of SN2 reaction (substitution nucleophilic bimolecular reaction) that involves the exchange of one halogen atom for another. It is an equilibrium reaction, bu ...
):Textbook of Practical Organic Chemistry, 5th Edition, Prentice Hall, 1989 :(CH3)2CHBr + NaI → (CH3)2CHI + NaBr


References

{{Organohalide-stub Iodoalkanes Isopropyl compounds Iodides