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Acetanilide is the organic compound with the formula . It is the N-acetylated derivative of aniline. It is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin.
The preparation used to be a traditional experiment in introductory organic chemistry lab classes,See, e.g., ; : the latter preparation includes the reduction of nitrobenzene to aniline. but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical techniques (especially recrystallization of the product) but which avoid the use of aniline, a suspected carcinogen.
Acetanilide is slightly soluble in water, and stable under most conditions. Pure crystals are plate shaped and appear colorless, white, or in between.
In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers.
During the same period of time, acetanilide was introduced into medical practice as a fever-reducing agent under the name Antifebrin. It was one of the first aniline derivatives found to possess analgesic and antipyretic properties. However, its use was later discontinued due to toxic side effects, including methemoglobinemia, which led to cyanosis.
Acetanilide-derived herbicides have been used since the 1960s or earlier. These include alachlor, metolachlor and
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