
Acetanilide is the
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula . It is the N-acetylated derivative of
aniline
Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
.
It is an odourless
solid
Solid is a state of matter where molecules are closely packed and can not slide past each other. Solids resist compression, expansion, or external forces that would alter its shape, with the degree to which they are resisted dependent upon the ...
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
A trade name, trading name, or business name is a pseudonym used by companies that do not operate under their registered company name. The term for this type of alternative name is fictitious business name. Registering the fictitious name with ...
Antifebrin.
Preparation and properties
Acetanilide can be produced by reacting
acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...
with
aniline
Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
:
[
: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
Paracetamol, or acetaminophen, is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain. It is a widely available over-the-counter drug sold under various brand names, including Tylenol and Panadol.
Parac ...
or aspirin
Aspirin () is the genericized trademark for acetylsalicylic acid (ASA), a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and inflammation, and as an antithrombotic. Specific inflammatory conditions that aspirin is ...
, both of which teach the same practical techniques (especially recrystallization of the product) but which avoid the use of aniline
Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
, a suspected carcinogen
A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...
.
Acetanilide is slightly soluble
In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution.
The extent of the solubi ...
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
Inhibitor or inhibition may refer to:
Biology
* Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity
* Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotransmi ...
of hydrogen peroxide
Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...
decomposition and is used to stabilize cellulose
Cellulose is an organic compound with the chemical formula, formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of glycosidic bond, β(1→4) linked glucose, D-glucose units. Cellulose is an important s ...
ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
varnish
Varnish is a clear Transparency (optics), transparent hard protective coating or film. It is not to be confused with wood stain. It usually has a yellowish shade due to the manufacturing process and materials used, but it may also be pigmente ...
es.[ It has also found uses in the intermediation in ]rubber
Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds.
Types of polyisoprene ...
accelerator synthesis, dyes and dye
Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy
Fantasy is a genre of speculative fiction that involves supernatural or Magic (supernatural), magical ele ...
intermediate synthesis, and camphor
Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (''Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the kapu ...
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 developer
In the Photographic processing, processing of photographic films, plates or papers, the photographic developer (or just developer) is one or more chemicals that convert the latent image to a visible image. Developing agents achieve this conversio ...
s.
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 herbicide
Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...
s have been used since the 1960s or earlier. These include alachlor
Alachlor is an herbicide from the chloroacetanilide family. It is an odorless, white solid. The greatest use of alachlor is for control of annual grasses and broadleaf weeds in crops. Use of alachlor is illegal in the European Union and no prod ...
, metolachlor
Metolachlor is an organic compound that is widely used as an herbicide. It is a derivative of aniline and is a member of the chloroacetanilide family of herbicides. It is highly effective toward grasses.
Agricultural use
Metolachlor was develo ...
and xylachlor
Xylachlor is a selective herbicide, used to pre-emergently control annual grasses on cereals, wheat, soy and rice. It is an anilide and a (chloro) acetanilide. As of 2023 it is considered obsolete, but may still be in use.
It was manufactured b ...
.
Pharmaceutical use
Acetanilide was the first aniline
Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
derivative found to possess analgesic
An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...
as well as antipyretic
An antipyretic (, from ''anti-'' 'against' and ' 'feverish') is a substance that reduces fever. Antipyretics cause the hypothalamus to override a prostaglandin-induced increase in temperature. The body then works to lower the temperature, which r ...
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
Cyanosis is the change of Tissue (biology), tissue color to a bluish-purple hue, as a result of decrease in the amount of oxygen bound to the hemoglobin in the red blood cells of the capillary bed. Cyanosis is apparent usually in the Tissue (bi ...
due to methemoglobinemia
Methemoglobinemia, or methaemoglobinaemia, is a condition of elevated methemoglobin in the blood. Symptoms may include headache, dizziness, shortness of breath, nausea, poor muscle coordination, and blue-colored skin (cyanosis). Complications ma ...
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
Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...
to paracetamol
Paracetamol, or acetaminophen, is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain. It is a widely available over-the-counter drug sold under various brand names, including Tylenol and Panadol.
Parac ...
(acetaminophen) in the human body, and that it was this metabolite that was responsible for the analgesic and antipyretic properties.[Multiple sources:
* .
*
* .
* Cahn, A., & Hepp, P. (1886). Das Antifebrin, ein neues Fiebermittel. ''Centralbl. Klin. Med.''
* 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 hydrolyzed
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolysi ...
to aniline in the body.
See also
* Nitroacetanilide
References
External links
{{Authority control
Photographic chemicals
Withdrawn drugs