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Acetanilide is the organic compound with the formula C6H5NHC(O)CH3. 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.




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, 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.




Applications


Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and is used to stabilize cellulose ester varnishes. It has also found uses in the intermediation in rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis. Acetanilide is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the sulfa drugs.
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.




= 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 metabolized to paracetamol (acetaminophen) in the human body, and that it was this metabolite that was responsible for the analgesic and antipyretic properties. The observed methemoglobinemia after acetanilide administration was ascribed to the small proportion of acetanilide that is hydrolyzed to aniline in the body.




See also


Nitroacetanilide




References






External links


NileRed (May 21, 2017). "Making an old pain and fever medication" by NileRed. YouTube.

Kata Kunci Pencarian:

• Acetanilide
• Patent medicine
• Bromo-Seltzer
• Paracetamol
• Aniline
• David Lester (biochemist)
• History of aspirin
• Nitroacetanilide
• Reaction inhibitor
• Butachlor

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Daftar Isi

• Acetanilide - Wikipedia
• Acetanilide | C8H9NO | CID 904 - PubChem
• SAFETY DATA SHEET - Fisher Sci
• Acetanilide | 103-84-4 - ChemicalBook
• Acetanilide - Wikiwand
• Acetanilide | synthesis, analgesic, antipyretic | Britannica
• Acetanilide - an overview | ScienceDirect Topics

Acetanilide - Wikipedia

Acetanilide is the organic compound with the formula C 6 H 5 NHC(O)CH 3. It is the N-acetylated derivative of aniline . [ 7 ] It is an odourless solid chemical of leaf or flake-like appearance.

Acetanilide | C8H9NO | CID 904 - PubChem

Acetanilide | C8H9NO | CID 904 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

SAFETY DATA SHEET - Fisher Sci

Product Name Acetanilide Cat No. : O1013-250 CAS No 103-84-4 Synonyms N-Phenylacetamide; Acetylaniline (Flakes/Certified) Recommended Use Laboratory chemicals. Uses advised against Food, drug, pesticide or biocidal product use. Details of the supplier of the safety data sheet Emergency Telephone Number CHEMTRECÒ, Inside the USA: 800-424-9300

Acetanilide | 103-84-4 - ChemicalBook

Jan 27, 2025 · Acetanilide, a para-aminophenol derivative with analgesic, antipyretic and weak antiinflammatory activity, was introduced into medicine in 1886. It subsequently proved to be excessively myelosuppressive and has been superseded by safer alternatives.

Acetanilide - Wikiwand

Acetanilide is the organic compound with the formula C6H5NHC(O)CH3. It is the N-acetylated derivative of aniline. It is an odourless solid chemical of leaf or f...

Acetanilide | synthesis, analgesic, antipyretic | Britannica

acetanilide, synthetic organic compound introduced in therapy in 1886 as a fever-reducing drug. Its effectiveness in relieving pain was discovered soon thereafter, and it was used as an alternative to aspirin for many years in treating such common complaints as headache, menstrual cramps, and rheumatism.

Acetanilide - an overview | ScienceDirect Topics

Moreover, other studies conducted according to present-day regulated guidelines are negative. Taken together, acetanilide was considered to be non-clastogenic in the in vivo micronucleus test. Based on the data available, acetanilide does not present a concern for genotoxic potential.