| Revision as of 19:54, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 470860904 of page Acetophenone for the Chem/Drugbox validation project (updated: ''). |
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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.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 443657077 |
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|verifiedrevid = 477239601 |
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| Name = Acetophenone |
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|Name = Acetophenone |
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| ImageFileL1 = Acetophenone-2D-skeletal.png |
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|ImageFile1 = File:Acetophenone-2D-skeletal.svg |
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|ImageName1 = Skeletal formula of the acetophenone molecule |
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| ImageSizeL1 = 120 px |
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|ImageSize1 = 150px |
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| ImageFileR1 = Acetophenone-from-xtal-3D-balls.png |
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|ImageFileL2 = Acetophenone-from-xtal-Mercury-3D-bs.png |
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| ImageSizeR1 = 140 px |
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|ImageNameL2 = Ball-and-stick model of the acetophenone molecule |
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| IUPACName = 1-phenylethanone |
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|ImageSizeL2 = 150px |
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| OtherNames = Phenyl methyl ketone, ACP, Phenylethanone |
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|ImageFileR2 = Acetophenone-from-xtal-Mercury-3D-sf.png |
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| Section1 = {{Chembox Identifiers |
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|ImageNameR2 = Space-filling model of the acetophenone molecule |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|ImageSizeR2 = 150px |
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| UNII = RK493WHV10 |
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|ImageFile3 = Ацетофенон.jpg |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|ImageName3 = sample of acetophenone |
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| KEGG = C07113 |
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|PIN = 1-Phenylethan-1-one<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 723 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4 | quote=The names acetophenone and benzophenone are retained only for general nomenclature, but no substitution is allowed.}}</ref> |
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| InChIKey = KWOLFJPFCHCOCG-UHFFFAOYAT |
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|OtherNames = Acetophenone<br />Phenylethanone<br />Methyl phenyl ketone |
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| PubChem = 7410 |
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|Section1={{Chembox Identifiers |
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| SMILES1 = CC(=O)c1ccccc1 |
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|Abbreviations = ACP |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| ChEMBL = 274467 |
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|UNII = RK493WHV10 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| StdInChI = 1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 |
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|KEGG = C07113 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|EC_number = 202-708-7 |
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| StdInChIKey = KWOLFJPFCHCOCG-UHFFFAOYSA-N |
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|RTECS = AM5250000 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 98-86-2 |
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|UNNumber = 1993 |
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|InChIKey = KWOLFJPFCHCOCG-UHFFFAOYAT |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|PubChem = 7410 |
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| ChemSpiderID = 7132 |
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|SMILES1 = CC(=O)c1ccccc1 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 27632 |
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|ChEMBL = 274467 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| DrugBank = DB04619 |
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|StdInChI = 1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 |
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| SMILES = O=C(c1ccccc1)C |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 |
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|StdInChIKey = KWOLFJPFCHCOCG-UHFFFAOYSA-N |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo = 98-86-2 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 7132 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEBI = 27632 |
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|DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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|DrugBank = DB04619 |
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|SMILES = O=C(c1ccccc1)C |
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|InChI = 1/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=8|H=8|O=1 |
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|C=8 | H=8 | O=1 |
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| Density = 1.028 g/cm³ |
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|Density = 1.028 g/cm<sup>3</sup> |
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| MeltingPt = 19–20 °C |
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|MeltingPtC = 19–20 |
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| BoilingPt = 202 °C |
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|BoilingPtC = 202 |
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| Solubility = 5.5 g/L at 25 °C<br/>12.2 g/L at 80 °C |
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|Solubility = 5.5 g/L at 25 °C<br/>12.2 g/L at 80 °C |
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|MagSus = -72.05·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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| Section7 = {{Chembox Hazards |
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| EUClass = {{Hazchem Xn}} |
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| ExternalMSDS = |
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| FlashPt = 77 °C |
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| NFPA-F = 2 |
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| NFPA-R = }} |
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}} |
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}} |
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|Section3={{Chembox Hazards |
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|ExternalSDS = |
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|FlashPtC = 77 |
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|NFPA-H = 1 |
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|NFPA-F = 2 |
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|NFPA-R = 0 |
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|GHSPictograms = {{GHS07}} |
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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|302|319}} |
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|PPhrases = {{P-phrases|264|270|280|301+312|305+351+338|330|337+313|501}} |
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}} |
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}} |
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'''Acetophenone''' is the ] with the ] C<sub>6</sub>H<sub>5</sub>C(O)CH<sub>3</sub>. It is the simplest aromatic ]. This colorless, viscous liquid is a precursor to useful ]s and fragrances.<ref name=Ullmann>{{Ullmann|first1=Hardo|last1=Siegel|first2=Manfred|last2=Eggersdorfer|title=Ketones|doi=10.1002/14356007.a15_077}}</ref> |
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==Production== |
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Acetophenone is formed as a byproduct of the ], the industrial route for the synthesis of ] and ]. In the Hock rearrangement of ], migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate ] of the intermediate: |
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:{{chem2 | C6H5C(CH3)2O2H -> C6H5C(O)CH3 + CH3OH }} |
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The cumene process is conducted on such a large scale that even the small amount of acetophenone by-product can be recovered in commercially useful quantities.<ref name=Ullmann/> |
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Acetophenone is also generated from ]. Ethylbenzene hydroperoxide is primarily converted to ] (α-methylbenzyl alcohol) in the process with a small amount of by-product acetophenone. Acetophenone is recovered or hydrogenated to 1-phenylethanol which is then dehydrated to produce styrene.<ref name=Ullmann/> |
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==Uses== |
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===Precursor to resins=== |
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Commercially significant ]s are produced from treatment of acetophenone with ] and a ]. The resulting ]s are conventionally described with the formula {{chem2|_{''n''} }}, resulting from ]. These substances are components of ]s and ]s. Modified acetophenone-formaldehyde resins are produced by the hydrogenation of the aforementioned ketone-containing resins. The resulting ] can be further crosslinked with ]s.<ref name=Ullmann/> The modified resins are found in coatings, inks and ]s. |
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===Niche uses=== |
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Acetophenone is an ingredient in fragrances that resemble ], ], ], ], and ]. It is used in chewing gum.<ref>{{Citation| last =Burdock| first =George A.| title =Fenaroli's Handbook of Flavor Ingredients| publisher =CRC Press| year =2005| edition =5th| page =15| url =https://books.google.com/books?id=A8OyTzGGJhYC&q=Fenaroli's%20handbook%20of%20flavor%20ingredients&pg=PP1| archive-url =https://web.archive.org/web/20140925024441/http://books.google.com/books?id=A8OyTzGGJhYC&lpg=PP1&dq=Fenaroli's%20handbook%20of%20flavor%20ingredients&pg=PP1| archive-date =2014-09-25| isbn =0-8493-3034-3| url-status =live}}</ref> |
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It is also listed as an approved ] by the U.S. FDA.<ref>{{cite web|url=http://www.accessdata.fda.gov/scripts/cder/iig/index.cfm|title=Inactive Ingredient Search for Approved Drug Products|url-status=live|archive-url=https://web.archive.org/web/20130504122045/http://www.accessdata.fda.gov/scripts/cder/iig/index.cfm|archive-date=2013-05-04}}</ref> |
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===Laboratory reagent=== |
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In instructional laboratories,<ref>{{cite journal |title= Polystyrene—A multistep synthesis: For the undergraduate organic chemistry laboratory |first1= Samuel H. |last1= Wilen |first2= Chester B. |last2= Kremer |first3= Irving |last3= Waltcher |journal= J. Chem. Educ. |year= 1961 |volume= 38 |issue= 6 |pages= 304–305 |doi= 10.1021/ed038p304 |bibcode= 1961JChEd..38..304W }}</ref> acetophenone is converted to ] in a two-step process that illustrates the reduction of carbonyls using ] and the ] of alcohols: |
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:{{chem2 | 4 C6H5C(O)CH3 + NaBH4 + 4 H2O -> 4 C6H5CH(OH)CH3 + NaOH + B(OH)3}} |
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:{{chem2 | C6H5CH(OH)CH3 -> C6H5CH\dCH2 + H2O}} |
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A similar two-step process is used industrially, but reduction step is performed by ] over a ] ]:<ref name=Ullmann/> |
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:{{chem2 | C6H5C(O)CH3 + H2 -> C6H5CH(OH)CH3 }} |
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Being ], acetophenone is also a popular test substrate for asymmetric ] experiments. |
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===Drugs=== |
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Acetophenone is used for the synthesis of many pharmaceuticals.<ref> |
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{{cite book |
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| isbn = 978-0-8155-1144-1 |
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| pages = , 177 |
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| last = Sittig |
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| first = Marshall |
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| title = Pharmaceutical Manufacturing Encyclopedia |
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| url = https://archive.org/details/pharmaceuticalma02sitt |
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| url-access = limited |
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| year = 1988 |
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}}</ref><ref> |
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{{cite book |
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| isbn =978-0-8493-9051-7 |
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| pages = 142–145 |
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| last1 = Gadamasetti |
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| first1 = Kumar |
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| last2= Tamim Braish |
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| title = Process Chemistry in the Pharmaceutical Industry, Volume 2 |
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| year = 2007 |
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| publisher = Taylor & Francis |
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}}</ref> |
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== Natural occurrence == |
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Acetophenone occurs naturally in many foods including ], ], ], ], ], and ]. It is also a component of ], the exudate from the castor sacs of the mature beaver.<ref>{{cite journal | title = Pheromonal activity of single castoreum constituents in beaver, Castor canadensis |last1=Müller-Schwarze|first1= D. |last2=Houlihan|first2= P. W. | journal = Journal of Chemical Ecology | date = April 1991 | volume = 17 | issue = 4 | doi = 10.1007/BF00994195 | pmid=24258917 | pages=715–34|bibcode=1991JCEco..17..715M |s2cid=29937875}}</ref> |
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== Pharmacology == |
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In the late 19th and early 20th centuries, acetophenone was used in medicine.<ref>{{Merck12th}}</ref> It was marketed as a ] and ] under brand name Hypnone. The typical dosage was 0.12 to 0.3 milliliters.<ref>{{cite book | last= Bartholow|first= Roberts | title = A Practical Treatise on Materia Medica and Therapeutics | publisher = Appleton & Co | date = 1908}}</ref> It was considered to have superior sedative effects to both ] and ].<ref>{{cite journal|last=Norman|first=Conolly|title=Cases illustrating the sedative effects of aceto-phenone|journal=Journal of Mental Science|volume=32|page=519|date=1887|doi=10.1192/bjp.32.140.519}}</ref> In humans, acetophenone is metabolized to ], ], and ].<ref>{{cite journal | title = Hypnone – The new hypnotic | journal = Journal of the American Medical Association | volume = 5 | page = 632 | date = 1885 | issue = 23 | doi = 10.1001/jama.1885.02391220016006}}</ref> ] occurs as an indirect metabolite and its quantity in urine may be used to confirm acetophenone exposure,<ref name=pubchem>{{PubChem|7410}}</ref> although other substances, like toluene, also induce hippuric acid in urine.<ref>{{cite web|url=http://www.beroepsziekten.nl/datafiles/A044.pdf|title=The Netherlands Center for Occupational Diseases (NCvB): toluene (Dutch)|website=beroepsziekten.nl|access-date=19 April 2018}}</ref> |
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== Toxicity == |
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The {{LD50}} is 815 mg/kg (oral, rats).<ref name=Ullmann/> Acetophenone is currently listed as a Group D ] indicating that there is no evidence at present that it causes cancer in humans. |
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== References == |
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{{reflist|30em}} |
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{{GABAAR PAMs}} |
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{{Authority control}} |
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