Nitroacetanilide

Nitroacetanilide is an organic compound that is used in various chemical reactions, particularly in the synthesis of pharmaceuticals. It is a derivative of aniline, a primary amine, and is characterized by the presence of a nitro group (-NO2) and an acetanilide group (C6H5NHCOCH3) in its molecular structure.

Structure and Properties

Nitroacetanilide is a white crystalline solid at room temperature. Its molecular formula is C8H8N2O3, and its molar mass is 180.16 g/mol. The compound is slightly soluble in water, but it dissolves readily in organic solvents such as ethanol and acetone.

The structure of nitroacetanilide consists of a benzene ring, to which an acetamide group (-NHCOCH3) and a nitro group (-NO2) are attached. The acetamide group is derived from acetic acid, while the nitro group is a common functional group in organic chemistry that contributes to the compound's reactivity.

Synthesis

Nitroacetanilide can be synthesized from acetanilide through a process known as nitration. This involves the reaction of acetanilide with a mixture of concentrated sulfuric acid and nitric acid. The reaction proceeds via an electrophilic aromatic substitution mechanism, in which the nitro group replaces a hydrogen atom on the benzene ring.

Applications

Due to its reactivity, nitroacetanilide is used as a starting material in the synthesis of various pharmaceutical compounds. For example, it can be reduced to aminoacetanilide, which is a key intermediate in the production of certain analgesics and antipyretics.

Safety

Like many nitro compounds, nitroacetanilide can be hazardous. It is important to handle it with care, using appropriate personal protective equipment. It should be stored in a cool, dry place, away from sources of ignition.