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style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 100-01-6 YesY
ChemSpider 7195
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula C6H6N2O2
Molar mass 138.12 g/mol
Appearance yellow or brown powder
Density 1.437 g/ml, solid
Melting point

146-149 °C(lit.)

Boiling point

332 °C

Solubility in water 0.8 mg/ml at 18.5°C (IPCS)
style="background: #F8EABA; text-align: center;" colspan="2" | Hazards
EU classification Toxic T Dangerous for the Environment (Nature) N
R-phrases R23/24/25 R33 R52/53
S-phrases S28 S36/37 S45 S61
NFPA 704
Flash point 199 °C
style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds
Related compounds 2-Nitroaniline, 3-Nitroaniline
 YesY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[1]
File:Synthesis of nitroaniline.svg


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


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.


  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 456-467.
  2. Williamson, Kenneth L. (2002). Macroscale and Microscale Organic Experiments, Fourth Edition. Houghton-Mifflin. ISBN 0618197028. 

External links

See also

it:4-nitroanilina nl:4-nitroaniline ja:4-ニトロアニリン pt:4-Nitroanilina