2-Nitroaniline

2-Nitroaniline
Skeletal formula of 2-nitroaniline
Ball-and-stick model of the 2-nitroaniline molecule
Names
Preferred IUPAC name
2-Nitroaniline
Systematic IUPAC name
2-Nitrobenzenamine
Other names
ortho-Nitroaniline
o-Nitroaniline
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.687
Properties
C6H6N2O2
Molar mass 138.13 g·mol−1
Appearance Orange solid
Density 1.442 g/mol
Melting point 71.5 °C (160.7 °F; 344.6 K)
0.117 g/100 ml (20°C) (SIDS)
-66.47·10−6 cm3/mol
Related compounds
Related compounds
 3-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

2-Nitroaniline is an organic chemical compound that is chemically described as an aniline carrying a nitro functional group in position 2. It is also classified as an aromatic amine. At ambient temperature and pressure, 2-nitroaniline is an orange solid.[1]

Synthesis

One method of preparing o-nitroaniline is via acetanilide. First, aniline acetylated with acetic anhydride.

C6H5NH2 + (CH3CO)2O → C6H5NHC(O)CH3 + CH3CO2H

In the next step, the acetanilide is nitrated:

C6H5NHC(O)CH3 + HNO3 → O2NC6H4NHC(O)CH3 + H2O

Finally, the nitroacetanilide is hydrolyzed:

O2NC6H4NHC(O)CH3 + H2O → O2NC6H4NH2 + CH3CO2H

Uses

2-Nitroaniline is the main precursor to phenylenediamines, which are converted to benzimidazoles, a family of heterocycles that are key components in pharmaceuticals.[2]

Reactions

One of the factors contributing to the reactivity of 2-nitroaniline is the relative positioning of the nitro and amine groups and their activating/deactivating properties. The nitrogroup is an electron withdrawing group deactivating ortho and para positions. This leaves meta position with electron density and more likely to undergo substitution. Reinforcing this reactivity, the amino group activates ortho and para with respect to the amine. The net effect is that these sites, which are also meta to the nitro group undergo reactions.

See also

References

  1. ↑ Safety data for o-nitroaniline
  2. ↑ Gerald Booth "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, 2007; Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_411
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