Acetanilide
862736
223588988
2008-07-04T19:33:56Z
Lightbot
7178666
Units/dates/other
{{Chembox new
| Name = '''Acetanilide'''
| ImageFile = Acetanilide.png
| ImageSize = 200px
| ImageFile1 = Acetanilide-3D-balls.png
| ImageSize1 = 200px
| ImageName = Acetanilide
| IUPACName = N-phenylacetamide
| Section1 = {{Chembox Identifiers
| CASNo = 103-84-4
| SMILES = O=C(C)Nc1ccccc1
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>8</sub>H<sub>9</sub>NO
| MolarMass = 135.17 g/mol
| Density = 1.219 g/cm³
| MeltingPt = 113–115 °C (235–239 °F)
| BoilingPt = 304 °C
| Solvent = other solvents
| Solubility = 0.1 g/100 mL at 22°C
}}
}}
'''Acetanilide'''<ref>[http://chemicalland21.com/lifescience/phar/ACETANILIDE.htm Acetanilide]</ref> 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'''.
==Formation==
Acetanilide can be produced by reacting [[acetic anhydride]] with either [[aniline]] or [[aniline|phenylammonium chloride]]
==Properties==
This compound is soluble in hot water. It has the ability to self-ignite if it reaches a temperature of 545 [[celsius|°C]], but is otherwise stable under most conditions<ref>[http://ptcl.chem.ox.ac.uk/MSDS/AC/acetanilide.html Safety data for acetanilide]</ref>. Pure crystals are plate shaped, white in colour, and have a sugary aftertaste.
==Applications==
Acetanilide is used as an [[Reaction inhibitor|inhibitor]] in [[hydrogen peroxide]] and is used to stabilize [[cellulose]] [[ester]] [[varnish]]es. It has also found uses in the intermediation in [[rubber]] accelerator synthesis, dyes and [[dye]] intermediate synthesis, and [[camphor]] synthesis. Acetanilide was used as a precursor in [[penicillin]] synthesis and other [[pharmaceutical]]s and its intermediates.
Acetanilide has [[analgesic]] and [[antipyretic]] ([[fever]]-reducing) properties; it is in the same class of drugs as acetaminophen ([[paracetamol]]). Under the name ''acetanilid'' it formerly figured in the formula of a number of [[patent medicine]]s and over the counter drugs. In 1948, [[Julius Axelrod]] and [[Bernard Brodie (pharmacologist)|Bernard Brodie]] discovered that acetanilide is much more toxic in these applications than other drugs, causing [[methemoglobinemia]] and ultimately doing damage to the [[liver]] and [[kidney]]s. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a [[metabolite]] of acetanilide and whose use Axelrod and Brodie suggested in the same study.
In the 19th century it was one of a large number of compounds used as experimental [[photographic developer]]s.
==Notes==
{{reflist|2}}
==External links==
*[http://physchem.ox.ac.uk/MSDS/AC/acetanilide.html Acetanilide MSDS]
[[Category:Acetanilides]]
[[Category:Photographic chemicals]]
[[bn:অ্যাসিটানিলাইড]]
[[de:Acetanilid]]
[[es:Acetanilida]]
[[fr:Acétanilide]]
[[it:Acetanilide]]
[[ja:アセトアニリド]]
[[no:Acetanilid]]
[[pl:Acetanilid]]
[[pt:Acetanilida]]
[[zh:乙醯苯胺]]