5-nitro-2-propoxyaniline

5-Nitro-2-propoxyaniline is a chemical compound used in the synthesis of various pharmaceuticals. It is a nitroaniline derivative, characterized by the presence of a nitro group (-NO2) and a propoxy group (-OCH2CH2CH3) attached to an aniline molecule.

Chemical Structure and Properties

5-Nitro-2-propoxyaniline is a yellowish solid with the molecular formula C9H12N2O3. It has a molar mass of 196.20 g/mol. The compound is characterized by the presence of a nitro group (-NO2) and a propoxy group (-OCH2CH2CH3) attached to an aniline molecule. The nitro group is a strong electron-withdrawing group, which makes the compound highly reactive. The propoxy group, on the other hand, is an electron-donating group, which increases the compound's stability.

Synthesis

The synthesis of 5-nitro-2-propoxyaniline involves the nitration of 2-propoxyaniline. This is typically achieved by reacting 2-propoxyaniline with a nitrating agent such as nitric acid in the presence of a catalyst. The reaction proceeds via an electrophilic aromatic substitution mechanism, with the nitro group replacing a hydrogen atom on the aniline ring.

Applications

5-Nitro-2-propoxyaniline is primarily used in the synthesis of various pharmaceuticals. It serves as a key intermediate in the production of drugs such as nitrofurantoin and nifuroxazide, which are used to treat bacterial infections. The compound's reactivity and stability make it a valuable tool in medicinal chemistry.

Safety and Precautions

As with all nitroaniline derivatives, 5-nitro-2-propoxyaniline should be handled with care. It is a potential skin and eye irritant and may cause respiratory irritation if inhaled. Proper safety measures, including the use of personal protective equipment (PPE), should be taken when handling this compound.