3-Nitroaniline
Names | |
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IUPAC name
3-Nitroaniline | |
Other names
meta-Nitroaniline, m-nitroaniline | |
Identifiers | |
99-09-2 | |
ChEMBL | ChEMBL14068 |
ChemSpider | 7145 |
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Jmol-3D images | Image |
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Properties | |
C6H6N2O2 | |
Molar mass | 138.14 g/mol |
Appearance | Yellow, Solid |
Melting point | 114 °C (237 °F; 387 K) |
Boiling point | 306 °C (583 °F; 579 K) |
0.1 g/100 ml (20°C) | |
Acidity (pKa) | 2.47 |
Related compounds | |
Related compounds |
2-Nitroaniline, 4-Nitroaniline |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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Infobox references | |
3-Nitroaniline, also known as 'meta'-nitroaniline and m-nitroaniline, is a non-volatile stable solid commonly used as a raw material for dyes. 3-Nitroaniline is an aniline carrying a nitro functional group in position 3. It is stable in neutral, acidic or alkaline solutions and is classified as "not readily biodegradable" with "low bioaccumulation potential" .
It is used as a chemical intermediate for azo coupling component 17 and the dyes disperse yellow 5 and acid blue 29. The chemical is changed to other substances (dyestuffs and m-nitrophenol) during the dyeing process.
Synthesis
It can be synthesised by nitration of benzamide followed by the Hofmann rearrangement of the 3-Nitrobenzamide previously formed. It consist in treating the 3-Nitrobenzamide with sodium hypobromite or sodium hypochlorite to transform the amide group into an amine.