4-Nitroaniline

From Wikipedia, the free encyclopedia
p-Nitroaniline
Other names

4-nitroaniline
1-amino-4-nitrobenzene
p-nitrophenylamine

Identifiers
CAS number 100-01-6 YesY
ChemSpider 13846959 N
UNII 1MRQ0QZG7G YesY
ChEMBL CHEMBL14282 N
Jmol-3D images Image 1
Properties
Molecular formula C6H6N2O2
Molar mass 138.12 g/mol
Appearance yellow or brown powder
Odor faint, ammonia-like
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)
Hazards
MSDS JT Baker
EU classification T N
R-phrases R23/24/25 R33 R52/53
S-phrases S28 S36/37 S45 S61
Main hazards Toxic
NFPA 704
1
2
0
Flash point 199 °C; 390 °F; 472 K
Related compounds
Related compounds 2-Nitroaniline, 3-Nitroaniline
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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. 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.

Synthesis

It is produced industrially via the amination of 4-nitrochlorobenzene:[1]

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.[2]

Applications

4-Nitroaniline is mainly consumed industrially as a precursor to p-phenylenediamine, an important dye. The reduction is effected using iron metal and by catalytic hydrogenation.[1]

It is a starting material for the synthesis of Para Red, the first Azo dye:[3]

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.

References

  1. ↑ 1.0 1.1 Gerald Booth "Nitro Compounds, Aromatic in Ullmann's Encyclopedia of Industrial Chemistry, 7th Ed.; Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411
  2. ↑ 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.
  3. ↑ Williamson, Kenneth L. (2002). Macroscale and Microscale Organic Experiments, Fourth Edition. Houghton-Mifflin. ISBN 0-618-19702-8. 

External links

See also

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.