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Revision as of 19:49, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 457425201 of page Acetanilide for the Chem/Drugbox validation project (updated: '').  Latest revision as of 02:09, 11 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443364206 | verifiedrevid = 477238648
| Name = Acetanilide | Name = Acetanilide
| ImageFile = Acetanilide.png | ImageFile = Acetanilid.svg
| ImageClass = skin-invert-image
| ImageSize = 200px | ImageSize = 170
⚫ | ImageFile1 = Acetanilide-3D-balls.png
| ImageFileL1 = Acetanilide Ball and Stick.png
| ImageSize1 = 200px
| ImageSizeL1 = 130
⚫ | ImageName = Acetanilide
⚫ | ImageFileR1 = Acetanilide Space Fill.png
| IUPACName = ''N''-phenylacetamide<br />''N''-phenylethanamide
| ImageSizeR1 = 130
⚫ | Section1 = {{Chembox Identifiers
⚫ | ImageName = Acetanilide
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
| PIN = ''N''-Phenylacetamide<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 846 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = ''N''-Phenyl derivatives of primary amides are called ‘anilides’ and may be named using the term ‘anilide’ in place of ‘amide’ in systematic or retained names of amides. (…) However, names expressing ''N''-substitution by a phenyl group on an amide are preferred IUPAC names.| chapter = Front Matter }}</ref>
| OtherNames = Acetanilide<ref name=iupac2013/><br />''N''-Phenylethanamide
⚫ |Section1={{Chembox Identifiers
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SP86R356CC | UNII = SP86R356CC
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C07565 | KEGG = C07565
| Beilstein = 606468
| Gmelin = 82833
| InChI = 1/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) | InChI = 1/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
| InChIKey = FZERHIULMFGESH-UHFFFAOYAA | InChIKey = FZERHIULMFGESH-UHFFFAOYAA
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 269644 | ChEMBL = 269644
Line 24: Line 29:
| StdInChIKey = FZERHIULMFGESH-UHFFFAOYSA-N | StdInChIKey = FZERHIULMFGESH-UHFFFAOYSA-N
| CASNo = 103-84-4 | CASNo = 103-84-4
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| EC-number = 203-150-7 | EC_number = 203-150-7
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 880 | ChemSpiderID = 880
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28884 | ChEBI = 28884
| PubChem = 904
| RTECS = AD7350000
| SMILES = O=C(Nc1ccccc1)C | SMILES = O=C(Nc1ccccc1)C
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Reference = <ref>{{RubberBible62nd|page=C-67}}.</ref><ref name="SIDS">{{SIDS-ref | title = Acetanilide | id = Acetanilide | date = September 2003}}.</ref> | Properties_ref = <ref>{{RubberBible62nd|page=C-67}}.</ref><ref name="SIDS">{{SIDS-ref | title = Acetanilide | id = Acetanilide | date = September 2003}}.</ref>
| C=8 | H=9 | N=1 | O=1
| Formula = C<sub>6</sub>H<sub>5</sub>NH(COCH<sub>3</sub>)
| Odor = Odorless
| MolarMass = 135.17 g/mol
| Density = 1.219 g/cm<sup>3</sup> | Density = 1.219 g/cm<sup>3</sup>
| MeltingPtC = 113-115
| MeltingPt = 114.3 ºC (236.7 ºF)
| BoilingPt = 304 °C (579 ºF) | BoilingPtC = 304
| Solubility = <0.1 g/100 mL at 22 °C | Dipole = 2.71
| Solubility = <0.56 g/100 mL (25 °C)
| SolubleOther = Soluble in ], ], ], ] | SolubleOther = Soluble in ], ], ], ]
| LogP = 1.16 (23 ºC) | LogP = 1.16 (23 °C)
| VaporPressure = 2 Pa (20 ºC) | VaporPressure = 2 Pa (20 °C)
| pKa = 0.5 (25 °C, H<sub>2</sub>O) (conjugate acid)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = ] | isbn = 9781498754293 | pages=5–88 | title-link = CRC Handbook of Chemistry and Physics }}</ref>}}
}}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| Hazards_ref = <ref name="MSDS">{{cite web| url = http://ptcl.chem.ox.ac.uk/MSDS/AC/acetanilide.html | archive-url = https://web.archive.org/web/20020623073536/http://ptcl.chem.ox.ac.uk/MSDS/AC/acetanilide.html | url-status = dead | archive-date = 2002-06-23 | title = Safety data for acetanilide | publisher = Physical Chemistry Laboratory, University of Oxford }}.</ref><ref>{{cite web|title=HSNO Chemical Classification Information Database|url-status=live|url=https://www.epa.govt.nz/database-search/chemical-classification-and-information-database-ccid/view/753A1DBD-C677-44DA-AF65-00F745A42660#:~:text=classification%20acute%20tox.|archive-url=https://web.archive.org/web/20221013183051/https://www.epa.govt.nz/database-search/chemical-classification-and-information-database-ccid/view/753A1DBD-C677-44DA-AF65-00F745A42660#:~:text=classification%20acute%20tox.|archive-date=October 13, 2022|location=New Zealand|publisher=]|access-date=August 26, 2009}}</ref>
| Reference = <ref>{{citation | title = HSNO Chemical Classification Information Database | url = http://www.ermanz.govt.nz/Chemicals/ChemicalDisplay.aspx?SubstanceID=12901 | publisher = New Zealand Environmental Risk Management Authority | accessdate = 2009-08-26 }}.</ref><ref name="MSDS">{{citation | url = http://ptcl.chem.ox.ac.uk/MSDS/AC/acetanilide.html | title = Safety data for acetanilide | publisher = Physical Chemistry Laboratory, University of Oxford}}.</ref>
| ExternalMSDS = | ExternalSDS =
⚫ | GHSPictograms = {{GHS exclamation mark|Acute Tox. (oral) 4}}
| EUIndex = Not listed
⚫ | GHSSignalWord = WARNING
⚫ | GHSPictograms = {{GHS exclamation mark|Acute Tox. (oral) 4}}
| HPhrases = {{H-phrases|302|373}}
⚫ | GHSSignalWord = WARNING
| HPhrases = {{H-phrases|302}} | PPhrases = {{P-phrases|264|270|301+312|330|501}}
| FlashPtC = 174
| PPhrases = {{P-phrases|264|270|301+312|330|501}}
| Autoignition = 545 ºC (1013 ºF) | AutoignitionPtC = 545
}} }}
}} }}

]]]

'''Acetanilide''' is the ] with the formula {{chem2|C6H5NHC(O)CH3}}. It is the N-acetylated derivative of ].<ref name=Ullmann>{{cite encyclopedia|author1=P. F. Vogt |author2=J. J. Gerulis|title=Amines, Aromatic|encyclopedia=Ullmann’s Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a02_037|isbn=9783527303854 }}</ref> It is an odourless ] chemical of leaf or flake-like appearance. It is also known as '''''N''-phenylacetamide''', '''acetanil''', or '''acetanilid''', and was formerly known by the ] '''Antifebrin'''.

==Preparation and properties==
Acetanilide can be produced by reacting ] with ]:<ref name=Ullmann/>
:C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> + (CH<sub>3</sub>CO)<sub>2</sub>O → C<sub>6</sub>H<sub>5</sub>NHCOCH<sub>3</sub> + CH<sub>3</sub>COOH

The preparation used to be a traditional experiment in introductory organic chemistry lab classes,<ref>See, e.g., {{citation | title = The preparation of acetanilide from aniline | url = http://wwwchem.uwimona.edu.jm/lab_manuals/c10expt23.html | publisher = Department of Chemistry, University of the West Indies at Mona, Jamaica | access-date = 2009-08-26}}; {{citation | first1 = Wilkins | last2 = Lowe | first2 = Valerie C. | title = Preparation of Acetanilide from Nitrobenzene | journal = J. Chem. Educ. | volume = 56 | issue = 7 | pages = 488 | year = 1979 | doi = 10.1021/ed056p488 | last1 = Reeve| bibcode = 1979JChEd..56..488R }}: the latter preparation includes the reduction of nitrobenzene to aniline.</ref> but it has now been widely replaced by the preparation of either ] or ], both of which teach the same practical techniques (especially ] of the product) but which avoid the use of ], a suspected ].

Acetanilide is slightly ] in water, and stable under most conditions.<ref name="MSDS"/> Pure crystals are plate shaped and appear colorless, white, or in between.

==Applications==
Acetanilide is used as an ] of ] decomposition and is used to stabilize ] ] ]es.<ref name=Ullmann/> It has also found uses in the intermediation in ] accelerator synthesis, dyes and ] intermediate synthesis, and ] synthesis.<ref>{{Cite web |last=PubChem |title=Acetanilide |url=https://pubchem.ncbi.nlm.nih.gov/compound/904 |access-date=2022-12-10 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> Acetanilide is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the ].<ref>{{cite book | title = Ashford's Dictionary of Industrial Chemicals | edition = Third | year = 2011 | page = 33}}</ref>

In the 19th century acetanilide was one of a large number of compounds used as experimental ]s.

===Pharmaceutical use===
Acetanilide was the first ] derivative found to possess ] as well as ] properties, and was quickly introduced into medical practice under the names of Antifebrin by A. Cahn and P. Hepp in 1886.<ref>{{citation | last1 = Cahn | first1 = A. | last2 = Hepp | first2 = P. | title = Das Antifebrin, ein neues Fiebermittel | journal = Centralbl. Klin. Med. | year = 1886 | volume = 7 | pages = 561–64}}.</ref> But its (apparent) unacceptable toxic effects, the most alarming being ] due to ] and ultimately liver and kidney damage,<ref name="Ax&Brodie">{{citation | last1 = Brodie | first1 = B. B. | last2 = Axelrod | first2 = J. | author-link2 = Julius Axelrod | title = The estimation of acetanilide and its metabolic products, aniline, ''N''-acetyl ''p''-aminophenol and ''p''-aminophenol (free and total conjugated) in biological fluids and tissues | journal = J. Pharmacol. Exp. Ther. | year = 1948 | volume = 94 | issue = 1 | pages = 22–28 | pmid = 18885610}}.</ref> prompted the search for supposedly less toxic aniline derivatives such as ].<ref name=pmid17227290>{{citation | last1 = Bertolini | first1 = A. | last2 = Ferrari | first2 = A. | last3 = Ottani | first3 = A. | last4 = Guerzoni | first4 = S. | last5 = Tacchi | first5 = R. | last6 = Leone | first6 = S. | title = Paracetamol: new vistas of an old drug | journal = CNS Drug Reviews | year = 2006 | volume = 12 | issue = 3–4 | pages = 250–75 | pmid = 17227290 | doi = 10.1111/j.1527-3458.2006.00250.x| pmc = 6506194 }}.</ref> After several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly ] to ] (acetaminophen) in the human body, and that it was this metabolite that was responsible for the analgesic and antipyretic properties.<ref name="Ax&Brodie"/><ref>Multiple sources:
*{{citation | first1 = D. | last1 = Lester | first2 = L. A. | last2 = Greenberg | title = Metabolic fate of acetanilide and other aniline derivatives. II. Major metabolites of acetanilide in the blood | journal = J. Pharmacol. Exp. Ther. | year = 1947 | volume = 90 | pages = 68–75 | pmid = 20241897 | issue = 1}}.
*{{citation | last1 = Brodie | first1 = B. B. | last2 = Axelrod | first2 = J. | author-link2 = Julius Axelrod | title = The fate of acetanilide in man | url = http://profiles.nlm.nih.gov/HH/A/A/A/D/_/hhaaad.pdf | journal = J. Pharmacol. Exp. Ther. | year = 1948 | volume = 94 | issue = 1 | pages = 29–38 | pmid = 18885611}}
*{{citation | first1 = Frederick B. | last1 = Flinn | first2 = Bernard B. | last2 = Brodie | title = The effect on the pain threshold of ''N''-acetyl ''p''-aminophenol, a product derived in the body from acetanilide | journal = J. Pharmacol. Exp. Ther. | year = 1948 | volume = 94 | issue = 1 | pages = 76–77 | pmid = 18885618}}.</ref> The observed methemoglobinemia after acetanilide administration was ascribed to the small proportion of acetanilide that is ] to aniline in the body.

==See also==
*]

==References==
{{reflist|30em}}

==External links==
{{cite AV media|url=https://www.youtube.com/watch?v=eQNLmkj_GBo|date=May 21, 2017|title="Making an old pain and fever medication" by NileRed|website=]|people=]}}

{{Prostanoidergics}}
{{Authority control}}

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