4-Nitroaniline

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.

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Synthesis

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.^[1]

Applications

4-Nitroaniline is a starting material for the synthesis of Para Red, the first azo dye:^[2]

Toxicity

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.

See also

• 2-Nitroaniline
• 3-Nitroaniline

References

1. ^ Mohrig, J.R.; Morrill, T.C.; Hammond, C.N.; Neckers, D.C. "Synthesis 5: Synthesis of the Dye Para Red from Aniline." Experimental Organic Chemistry. Freeman: New York, NY, 1997; pp 456-67.
2. ^ Williamson, Kenneth L. (2002). Macroscale and Microscale Organic Experiments, Fourth Edition. Houghton-Mifflin. ISBN 0618197028. 

• Safety (MSDS)data for p-nitroaniline
• Sigma-Aldrich Catalog data