3-Nitroaniline

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3-Nitroaniline
3-nitroaniline chemical structure.png
Identifiers
CAS number 99-09-2 YesY
ChemSpider 7145 YesY
ChEMBL CHEMBL14068 YesY
Jmol-3D images Image 1
Properties
Molecular formula 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)
Solubility in water 0.1 g/100 ml (20°C)
Acidity (pKa) 2.47
Related compounds
Related compounds 2-Nitroaniline, 4-Nitroaniline
Except where noted otherwise, data are 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" [1].

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[edit]

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.

See also[edit]

References[edit]