The key difference between aniline and benzylamine is that the amine group of aniline is attached to the benzene ring directly whereas the amine group of benzylamine is attached to the benzene ring indirectly, through a –CH2– group.
Aniline and benzylamine are aromatic organic compounds. Both these compounds contain benzene rings and amine groups, but the amine group attach the benzene in different ways; either directly or indirectly. Therefore, the two compounds have different chemical and physical properties.
CONTENTS
1. Overview and Key Difference
2. What is Aniline
3. What is Benzylamine
4. Side by Side Comparison – Aniline vs Benzylamine in Tabular Form
5. Summary
What is Aniline?
Aniline is an aromatic organic compound having the chemical formula C6H5NH2. It has a phenyl group (a benzene ring) with an attached amine group (-NH2). It is the simplest aromatic amine. Moreover, this compound is slightly pyramidalized and is flatter than an aliphatic amine. Its molar mass is 93.13 g/mol. The melting point is −6.3 °C while the boiling point is 184.13 °C. It has the odour of rotten fish.
Industrially, we can produce this compound via two steps. The first step is the nitration of benzene with a concentrated mixture of nitric acid and sulfuric acid (at 50 to 60 °C). It gives nitrobenzene. Then, we can hydrogenate nitrobenzene into aniline in the presence of a metal catalyst. The reaction is as follows;
Furthermore, this compound is mainly used in the manufacture of polyurethane precursors. Apart from that, we can use this compound in the production of dyes, drugs, explosive materials, plastics, photographic and rubbery chemicals, etc.
What is Benzylamine?
Benzylamine is an aromatic organic compound with the chemical formula C6H5CH2NH2. It has an amine group attached to a phenyl group via a –CH2- group. Besides, this compound occurs as a colourless liquid, and it has an ammonia-like odour. The molar mass of Benzylamine is 107.15 g/mol. The melting point is 10 °C while the boiling point is 185 °C.
We can produce this compound via the reaction of benzyl chloride with ammonia. Also, we can produce it by benzonitrile reduction. The reaction is as follows;
Moreover, this compound is a common precursor for organic synthesis and the production of many pharmaceuticals.
What is the Difference Between Aniline and Benzylamine?
Aniline is an aromatic organic compound having the chemical formula C6H5NH2 while Benzylamine is an aromatic organic compound that has the chemical formula C6H5CH2NH2. The key difference between aniline and benzylamine is that in aniline the amine group attaches with the benzene ring directly whereas in benzylamine the amine group attaches the benzene ring indirectly, through a –CH2- group.
Moreover, we can produce aniline via nitration of benzene followed by hydrogenation nitrobenzene into aniline whereas we can produce benzylamine via reaction of benzyl chloride with ammonia. Besides, a further difference between aniline and benzylamine is their odour. Aniline has the odour of rotten fish while the odour of benzylamine is similar to the odour of ammonia.
Summary – Aniline vs Benzylamine
Aniline is an aromatic organic compound having the chemical formula C6H5NH2 while Benzylamine is an aromatic organic compound which has the chemical formula C6H5CH2NH2. In summary, the key difference between aniline and benzylamine is that in aniline, the amine group attaches with the benzene ring directly whereas, in benzylamine, the amine group attaches the benzene ring indirectly, through a –CH2– group.
Reference:
1. “Aniline.” Encyclopædia Britannica, Encyclopædia Britannica, Inc., 26 Sept. 2013, Available here.
Image Courtesy:
1. “Aniline from Nitrobenzene” By Hermann Luyken – Own work (CC0) via Commons Wikimedia
2. “Benzonitrile hydrogenation” By Hermann Luyken – Own work (CC BY-SA 3.0) via Commons Wikimedia