|Jmol-3D images||Image 1|
|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)|
|EU classification||T N|
|R-phrases||R23/24/25 R33 R52/53|
|S-phrases||S28 S36/37 S45 S61|
|Flash point||199 °C (390 °F; 472 K)|
|Related compounds||2-Nitroaniline, 3-Nitroaniline|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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. 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.
- ClC6H4NO2 + 2 NH3 → H2NC6H4NO2 + NH4Cl
Below is a laboratory 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.
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.
- Gerald Booth "Nitro Compounds, Aromatic in Ullmann's Encyclopedia of Industrial Chemistry, 7th Ed.; Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411
- 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.
- Williamson, Kenneth L. (2002). Macroscale and Microscale Organic Experiments, Fourth Edition. Houghton-Mifflin. ISBN 0-618-19702-8.
- Safety (MSDS)data for p-nitroaniline
- MSDS Sheet for p-nitroaniline
- Sigma-Aldrich Catalog data
- CDC - NIOSH Pocket Guide to Chemical Hazards