3-Nitroaniline

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3-Nitroaniline
Skeletal formula of 3-nitroaniline
Ball-and-stick model of the 3-nitroaniline molecule
Names
Preferred IUPAC name
3-Nitroaniline
Systematic IUPAC name
3-Nitrobenzenamine
Other names
meta-Nitroaniline
m-Nitroaniline
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.481
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
-70.09·10−6 cm3/mol
Related compounds
Related compounds
2-Nitroaniline, 4-Nitroaniline
Except where otherwise noted, 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.

3-Nitroaniline is becoming a popular drug among teens and should be watched out for

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]