Formula C6H6N2O2 Density 1.442 g/cm³ | Molar mass 138.14 g/mol Appearance Orange solid | |
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Solubility sphere of 2 nitroaniline
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.
Contents
Synthesis
One method of preparing o-nitroaniline is via acetanilide. First, aniline acetylated with acetic anhydride.
C6H5NH2 + (CH3CO)2O → C6H5NHC(O)CH3 + CH3CO2HIn the next step, the acetanilide is nitrated:
C6H5NHC(O)CH3 + HNO3 → O2NC6H4NHC(O)CH3 + H2OFinally, the nitroacetanilide is hydrolyzed:
O2NC6H4NHC(O)CH3 + H2O → O2NC6H4NH2 + CH3CO2HUses
2-Nitroaniline is the main precursor to phenylenediamines, which are converted to benzimidazoles, a family of heterocycles that are key components in pharmaceuticals.
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.