3-Nitroaniline, also known as ''meta''-nitroaniline and ''m''-nitroaniline, is a non-volatile stable
solid
Solid is one of the State of matter#Four fundamental states, four fundamental states of matter (the others being liquid, gas, and Plasma (physics), plasma). The molecules in a solid are closely packed together and contain the least amount o ...
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 and ...
.
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
In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...
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 rest ...
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 sequ ...
or
alkaline
In chemistry, an alkali (; from ar, القلوي, al-qaly, lit=ashes of the saltwort) is a base (chemistry), basic, ionic compound, ionic salt (chemistry), salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as ...
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 and ...
of benzamide
Benzamide is a organic compound with the chemical formula of C6H5C(O)NH2. It is the simplest amide derivative of benzoic acid
Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benz ...
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
Sodium hypobromite is the inorganic compound with the formula NaBrO. It is usually obtained as the pentahydrate, so the material that is usually called sodium hypobromite has the formula NaOBr • 5H2O. It is a yellow-orange solid tha ...
or sodium hypochlorite
Sodium hypochlorite (commonly known in a dilute solution as bleach) is an Inorganic chemistry, inorganic chemical compound with the chemical formula, formula NaOCl (or NaClO), comprising a sodium cation () and a hypochlorite anion (or ). It may ...
to transform the amide group into an amine.
See also
* 2-Nitroaniline
* 4-Nitroaniline
4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, ...
References
{{DEFAULTSORT:Nitroaniline, 3-
Anilines
Nitrobenzenes