2-Iodobenzoic acid
Encyclopedia
2-Iodobenzoic acid, or o-iodobenzoic acid, is an organic compound
with the formula IC6H4COOH. The synthesis of 2-iodobenzoic acid via the diazotization of anthranilic acid
is a common performed in university organic chemistry labs.
consisting of the diazotization of anthranilic acid
followed by a diazo replacement. First anthranilic acid is treated with nitrous acid
in order to convert the amino group into the diazo
group. The diazo group is ejected, yielding a carbocation which is then attacked by the highly nucleophilic I- anion.
The nitrous acid is usually generated in situ from sodium nitrite
.
Compound
Compound may refer to:* Chemical compounds, combinations of two or more elements* Compound , a cluster of buildings having a shared purpose, usually inside a fence or wall...
with the formula IC6H4COOH. The synthesis of 2-iodobenzoic acid via the diazotization of anthranilic acid
Anthranilic acid
Anthranilic acid is the organic compound with the formula C6H4COOH. This amino acid is a white solid when pure, although commercial samples may appear yellow. The molecule consists of a benzene ring with two adjacent functional groups, a carboxylic acid and an amine...
is a common performed in university organic chemistry labs.
Synthesis
2-Iodobenzoic acid can be synthesized via a Sandmeyer reactionSandmeyer 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....
consisting of the diazotization of anthranilic acid
Anthranilic acid
Anthranilic acid is the organic compound with the formula C6H4COOH. This amino acid is a white solid when pure, although commercial samples may appear yellow. The molecule consists of a benzene ring with two adjacent functional groups, a carboxylic acid and an amine...
followed by a diazo replacement. First anthranilic acid is treated with nitrous acid
Nitrous acid
Nitrous acid is a weak and monobasic acid known only in solution and in the form of nitrite salts.Nitrous acid is used to make diazides from amines; this occurs by nucleophilic attack of the amine onto the nitrite, reprotonation by the surrounding solvent, and double-elimination of water...
in order to convert the amino group into the diazo
Diazo
Diazo refers to a type of organic compound called diazo compound that has two linked nitrogen atoms as a terminal functional group. The general formula is R2C=N2. The simplest example of a diazo compound is diazomethane...
group. The diazo group is ejected, yielding a carbocation which is then attacked by the highly nucleophilic I- anion.
The nitrous acid is usually generated in situ from 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...
.