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4-Nitroaniline

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p-Nitroaniline
p-nitroaniline
Names
Other names
4-nitroaniline
1-amino-4-nitrobenzene
p-nitrophenylamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.555 Edit this at Wikidata
UNII
  • InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2 ☒N
    Key: TYMLOMAKGOJONV-UHFFFAOYSA-N ☒N
  • InChI=1/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2
    Key: TYMLOMAKGOJONV-UHFFFAOYAW
  • c1cc(ccc1N)N(=O)=O
Properties
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
0.8 mg/ml at 18.5°C (IPCS)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 199 °C (390 °F; 472 K)
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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]

Synthesis of Para Red
Synthesis of Para Red

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. ^ a b 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.

See also

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