3-Nitroaniline, also known as ''meta''-nitroaniline and ''m''-nitroaniline, is a non-volatile stable

solid Solid is one of the four fundamental states of matter (the others being liquid, gas, and plasma). The molecules in a solid are closely packed together and contain the least amount of kinetic energy. A solid is characterized by structur ...

commonly used as a raw material for

dyes A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution an ...

. 3-Nitroaniline is an

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starti ...

carrying a

nitro Nitro may refer to: Chemistry *Nitrogen, a chemical element and a gas except at very low temperatures, with which many compounds are formed: **Nitro compound, an organic compound containing one or more nitro functional groups, -NO2 **Nitroalkene, ...

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the r ...

in position 3. It is stable in neutral,

acidic In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a ...

alkaline In chemistry, an alkali (; from ar, القلوي, al-qaly, lit=ashes of the saltwort) is a basic, ionic salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as a base that dissolves in water. A solution of a ...

solutions and is classified as "not readily biodegradable" with "low bioaccumulation potential". It is used as a chemical intermediate for

azo coupling In organic chemistry, an azo coupling is an organic reaction between a diazonium compound () and another aromatic compound that produces an azo compound (). In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the ...

component 17 and the dyes disperse yellow 5 and acid blue 29. The chemical is changed to other substances (dyestuffs and ''m''-nitrophenol) during the dyeing process.

Synthesis

It can be synthesized by

nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols an ...

benzamide Benzamide is a organic compound with the chemical formula of C6H5C(O)NH2. It is the simplest amide derivative of benzoic acid. In powdered form, it appears as a white solid, while in crystalline form, it appears as colourless crystals. It is slig ...

followed by the

Hofmann rearrangement The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one fewer carbon atom. The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to gi ...

of the 3-nitrobenzamide previously formed. It consist in treating the 3-nitrobenzamide with sodium hypobromite or

sodium hypochlorite Sodium hypochlorite (commonly known in a dilute solution as bleach) is an inorganic chemical compound with the formula NaOCl (or NaClO), comprising a sodium cation () and a hypochlorite anion (or ). It may also be viewed as the sodium s ...

to transform the amide group into an amine.

References

{{DEFAULTSORT:Nitroaniline, 3- Anilines Nitrobenzenes

Synthesis

See also

References