Neha Patil (Editor)

2 Nitroaniline

Updated on
Share on FacebookTweet on TwitterShare on LinkedInShare on Reddit
Covid-19
Formula  C6H6N2O2
Density  1.442 g/cm³
Molar mass  138.14 g/mol
Appearance  Orange solid
2-Nitroaniline httpsuploadwikimediaorgwikipediacommons77
Related compounds  3-Nitroaniline, 4-Nitroaniline

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

2-Nitroaniline 4Methyl2nitroaniline896231HNMR

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 2nitroaniline C6H6N2O2 ChemSynthesis

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

Reactions

2-Nitroaniline 2Nitroaniline C6H6N2O2 ChemSpider

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.

References

2-Nitroaniline Wikipedia


Similar Topics
Maya Burman
Danny Nikolic
Chezhiyan
Topics
 
B
i
Link
H2
L