4-Nitroaniline

p-Nitroaniline
Other names 4-nitroaniline 1-amino-4-nitrobenzene p-nitrophenylamine
Identifiers
CAS number	100-01-6 Y
ChemSpider	13846959 N
UNII	1MRQ0QZG7G Y
ChEMBL	CHEMBL14282 N
Jmol-3D images	Image 1
SMILES c1cc(ccc1N)N(=O)=O
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
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)
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
Related compounds
Related compounds	2-Nitroaniline, 3-Nitroaniline
N (verify) (what is: Y/N?) 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. 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

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]

Applications

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

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. ^ 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 0-618-19702-8. 

External links

• Safety (MSDS)data for p-nitroaniline
• MSDS Sheet for p-nitroaniline
• Sigma-Aldrich Catalog data

See also

• 2-Nitroaniline
• 3-Nitroaniline