4-Nitroaniline
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| p-Nitroaniline | |
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| Other names | 4-nitroaniline 1-amino-4-nitrobenzene p-nitrophenylamine |
| Identifiers | |
| CAS number | [100-01-6] |
| 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 | <0.1 mg/ml at 21°C |
| Hazards | |
| Flash point | 199 °C |
| Related compounds | |
| Related compounds | 2-Nitroaniline, 3-Nitroaniline |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.
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[edit] 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]
[edit] Applications
4-Nitroaniline is a starting material for the synthesis of Para Red, the first azo dye:[2]
[edit] 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.
[edit] See also
[edit] References
- ^ 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 456-67.
- ^ Williamson, Kenneth L. (2002). Macroscale and Microscale Organic Experiments, Fourth Edition. Houghton-Mifflin. ISBN 0618197028.
