Iodobenzene is an organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 consisting of a benzene

Benzene

Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

 ring substitituted with one iodine

Iodine

Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....

 atom. It is useful as a synthetic intermediate in organic chemistry

Organic chemistry

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

.

Preparation

Iodobenzene is commercially available, but it may be prepared in the laboratory from aniline

Aniline

Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...

 via the Sandmeyer reaction

Sandmeyer reaction

The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts. It is named after the Swiss chemist Traugott Sandmeyer....

. In the first step, the amine

Amine

Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...

 functional group is diazotized

Diazonium compound

Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group R-N2+ X- where R can be any organic residue such alkyl or aryl and X is an inorganic or organic anion such as a halogen...

 with hydrochloric acid

Hydrochloric acid

Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....

 and sodium nitrite

Sodium nitrite

Sodium nitrite is the inorganic compound with the chemical formula NaNO2. It is a white to slight yellowish crystalline powder that is very soluble in water and is hygroscopic...

. Potassium iodide

Potassium iodide

Potassium iodide is an inorganic compound with the chemical formula KI. This white salt is the most commercially significant iodide compound, with approximately 37,000 tons produced in 1985. It is less hygroscopic than sodium iodide, making it easier to work with...

 is added to the resultant diazonium chloride, causing nitrogen

Nitrogen

Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...

 gas to evolve. Any excess nitrite is hydrolyzed with a strong base; the mixture is acidified and the desired product is separated by steam distillation.

Alternatively, it may be produced by refluxing iodine

Iodine

Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....

 and nitric acid

Nitric acid

Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosive and toxic strong acid.Colorless when pure, older samples tend to acquire a yellow cast due to the accumulation of oxides of nitrogen. If the solution contains more than 86% nitric acid, it is referred to as fuming...

 with benzene.

Reactions

Since the C–I bond is weaker than C–Br or C–Cl, iodobenzene is more reactive than bromobenzene or chlorobenzene

Chlorobenzene

Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.-Uses:...

. Iodobenzene can react with magnesium

Magnesium

Magnesium is a chemical element with the symbol Mg, atomic number 12, and common oxidation number +2. It is an alkaline earth metal and the eighth most abundant element in the Earth's crust and ninth in the known universe as a whole...

 to form the Grignard reagent, phenylmagnesium iodide. Phenylmagnesium iodide, like the bromide analog

Phenylmagnesium bromide

Phenylmagnesium bromide, with the simplified formula , is a magnesium-containing organometallic compound. It is so commonly used that it is commercially available as a solution in diethyl ether or tetrahydrofuran . Phenylmagnesium bromide is a Grignard reagent...

, is a synthetic equivalent for the phenyl anion synthon

Synthon

A synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible synthetic operation. The term was coined by E.J. Corey...

. Iodobenzene reacts with chlorine to give the complex, iodobenzene dichloride

Iodobenzene dichloride

Iodobenzene dichloride is a complex of iodobenzene with chlorine. It is used as an oxidant.Single-crystal X-ray crystallography has been used to determine its structure; as can be predicted by VSEPR theory, it adopts a T-shaped geometry about the central iodine atom.-Preparation:Iodobenzene...

, which is used as an oxidant.

Iodobenzene can also serve as a substrate

Substrate (chemistry)

In chemistry, a substrate is the chemical species being observed, which reacts with a reagent. This term is highly context-dependent. In particular, in biochemistry, an enzyme substrate is the material upon which an enzyme acts....

 for the Sonogashira coupling

Sonogashira coupling

In organic chemistry, a Sonogashira coupling is a coupling reaction of terminal alkynes with aryl or vinyl halides. This reaction was first reported by Kenkichi Sonogashira and Nobue Hagihara in 1975.-Catalyst:...

, Heck reaction

Heck reaction

The Heck reaction is the chemical reaction of an unsaturated halide with an alkene and a base and palladium catalyst to form a substituted alkene. Together with the other palladium-catalyzed cross-coupling reactions, this reaction is of great importance, as it allows one to do substitution...

, and other metal-catalyzed couplings.

Further reading

• Gattermann-Wieland, "Laboratory Methods of Organic Chemistry," p. 283. Translated from the twenty-fourth German edition by W. McCartney, The Macmillan Company, New York, 1937.