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4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. It is an organic chemical compound, consisting of a phenyl group attached to an amino group which is para to a nitro group. The chemical structure of p-nitroaniline is shown at the right. This chemical is commonly used as an intermediate in the synthesis of dyes, antioxidants, pharmaceuticals and gasoline, in gum inhibitors, poultry medicines, and as a corrosion inhibitor.
Below is an example synthesis of p-nitroaniline from aniline. The key step in this reaction sequence is an electrophilic aromatic substitution to install the nitro group para to the amino group. After this reaction, a separation must be performed to remove 2-nitroaniline, which is also formed in a small amount during the reaction.
4-Nitroaniline is a starting material for the synthesis of Para Red, the first azo dye:
The compound is toxic by way of inhalation, ingestion, and absorption, and should be handled with care. Its LD50 in rats is 750 mg/kg when administered orally. p-Nitroaniline is particularly harmful to all aquatic organisms, and can cause long-term damage to the environment if released as a pollutant.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "4-Nitroaniline". A list of authors is available in Wikipedia.|