3-Nitroaniline

3-Nitroaniline

Skeletal formula of 3-nitroaniline Ball-and-stick model of the 3-nitroaniline molecule
Names
IUPAC name 3-Nitroaniline
Other names meta-Nitroaniline, m-nitroaniline
Identifiers
CAS Number	99-09-2 Y
ChEMBL	ChEMBL14068 Y
ChemSpider	7145 Y
Jmol 3D model	Interactive image
InChI InChI=1S/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2 Y Key: XJCVRTZCHMZPBD-UHFFFAOYSA-N Y InChI=1/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2 Key: XJCVRTZCHMZPBD-UHFFFAOYAY
SMILES O=[N+]([O-])c1cccc(N)c1
Properties
Chemical 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
Vapor pressure	{{{value}}}
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.

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.

See also

• 2-Nitroaniline
• 4-Nitroaniline

References

• UNEP PDF on m-Nitroaniline