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[[methemoglobinemia]] and ultimately doing damage to the [[liver]] and [[kidney]]s. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a [[metabolite]] of acetanilide and whose use Axelrod and Brodie suggested in the same study.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]]