Nitrobenzene: Structure, Formula & Uses

Instructor: Laura Foist

Laura has a Masters of Science in Food Science and Human Nutrition and has taught college Science.

In this lesson, we will learn about nitrobenzene, an aromatic derivative of benzene. We will learn about its properties, how it is produced, and how it is typically used.

Nitrobenzene Properties and Uses

When working with nitrobenzene, we must be very careful because it is extremely toxic. Although it has a pleasant almond-like smell, it will not be good to ingest, inhale, or even to spread on your skin. It can be used commercially to cover up other unpleasant smells, as long as it will not be used for human or animal consumption. Due to its toxicity, it is not frequently used as nitrobenzene, but instead it is used as a precursor for another compound, aniline.

The parent compound of nitrobenzen, benzene, is a very stable compound since it is fully conjugated. So, it can be very difficult to add substituents onto the benzene if that conjugation is disturbed. Some substituents make it even more stable by furthering the conjugation, and this is why reactions move towards these products. Nitrobenzene is one of these substituents since pie bonding on the nitrogen and both oxygens allows electrons to be shared on the nitrogen and each oxygen. Nitrobenzene deactivates the benzene ring so that it is even less reactive to nitration, halogenation, and sulfonation. And, reactions are only able to occur at the meta-position, which further decreases the reactivity of benzene.

Although the benzene ring is now very unreactive, the nitro portion is able to react further to make aniline. By reducing the nitro to a primary amine, using a strong acid (such as HCl) in an oxygen/reduction reaction aniline can be produced. This is the most common use of nitrobenzene (approximately 97% of nitrobenzene is used to produce aniline). Aniline is a precursor for rubber, pesticides, explosives, and many other products.

Aniline is made by reducing the nitro group on the benzene

The remaining 3% of nitrobenzene is used as a solvent in electrophilic reactions or as a mask for unpleasant smells in paints, floor polishes, and other unpleasant-smelling compounds. But, it is very toxic and readily absorbed into the skin, making it not very useful in many compounds.

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