| p-Nitroaniline | |
|---|---|
|
Other names
4-nitroaniline |
|
| Identifiers | |
| CAS number | 100-01-6 |
| ChemSpider | 7195 |
| UNII | 1MRQ0QZG7G |
| ChEMBL | CHEMBL14282 |
| 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 |
| (verify) (what is: /?) 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. The chemical structure of p-nitroaniline is shown at the right. 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.
Contents |
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]
4-Nitroaniline is a starting material for the synthesis of Para Red, the first Azo dye:[2]
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.