4-Nitroaniline

p-Nitroaniline

Skeletal formula of p-nitroaniline Ball-and-stick model of the p-nitroaniline molecule
Names
Other names 4-nitroaniline 1-amino-4-nitrobenzene p-nitrophenylamine
Identifiers
CAS Number	100-01-6 Y
ChEBI	CHEBI:17064 N
ChEMBL	ChEMBL14282 N
ChemSpider	13846959 N
Jmol 3D model	Interactive image
UNII	1MRQ0QZG7G Y
InChI 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
SMILES c1cc(ccc1N)N(=O)=O
Properties
Chemical 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 to 149 °C (295 to 300 °F; 419 to 422 K) (lit.)
Boiling point	332 °C (630 °F; 605 K)
Solubility in water	0.8 mg/ml at 18.5 °C (IPCS)
Vapor pressure	0.00002 mmHg (20°C)
Vapor pressure	{{{value}}}
Related compounds
Related compounds	2-Nitroaniline, 3-Nitroaniline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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:

ClC₆H₄NO₂ + 2 NH₃ → H₂NC₆H₄NO₂ + NH₄Cl

Below is a laboratory synthesis of 4-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.
File:Synthesis of nitroaniline.svg

Applications

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

It is a starting material for the synthesis of Para Red, the first azo dye:

When heated, it polymerizes explosively into a rigid foam.

Synthesis of Para Red

Laboratory use

Nitroaniline is a solvatochromic dye used for determining Kamlet-Taft solvent parameters. The position of its UV-visual peak changes with the balance of hydrogen bonding acceptors and donors in the solvent.

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. 4-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

External links

• Safety (MSDS)data for p-nitroaniline
• MSDS Sheet for p-nitroaniline
• Sigma-Aldrich Catalog data
• CDC - NIOSH Pocket Guide to Chemical Hazards