ortho-nitroaniline, o-nitroaniline, 2-nitrobenzenamine,
|Jmol interactive 3D||Image|
|Molar mass||138.13 g·mol−1|
|Melting point||71.5 °C (160.7 °F; 344.6 K)|
|0.117 g/100 ml (20°C) (SIDS)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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.
- 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
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 ot the amine. The net effect is that these sites, which are also meta to the nitro group undergo reactions.