Acetanilide is the organic compound with the formula . It is the N-acetylated derivative of aniline.
Preparation and properties
Acetanilide can be produced by reacting
acetic anhydride with
aniline:
[
]
- C6H5NH2 + (CH3CO)2O → C6H5NHCOCH3 + CH3COOH
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.
Applications
Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and is used to stabilize cellulose ester .[ It has also found uses in the intermediation in rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis.]
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.
Acetanilide-derived have been used since the 1960s or earlier. These include alachlor, metolachlor and
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Pharmaceutical use
Acetanilide was the first aniline derivative found to possess analgesic as well as antipyretic properties, and was quickly introduced into medical practice under the names of Antifebrin by A. Cahn and P. Hepp in 1886.[.] But its (apparent) unacceptable toxic effects, the most alarming being cyanosis due to methemoglobinemia and ultimately liver and kidney damage,[.] prompted the search for supposedly less toxic aniline derivatives such as phenacetin.[.] After several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly Metabolism to paracetamol (acetaminophen) in the human body, and that it was this metabolite that was responsible for the analgesic and antipyretic properties.[Multiple sources:
]
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Cahn, A., & Hepp, P. (1886). Das Antifebrin, ein neues Fiebermittel. Centralbl. Klin. Med.
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Brodie, B. B., & Axelrod, J. (1948). The fate of acetanilide in man. Journal of Pharmacology and Experimental Therapeutics, 94(1), 29–38.
The observed methemoglobinemia after acetanilide administration was ascribed to the small proportion of acetanilide that is Hydrolysis to aniline in the body.
See also
External links
