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P-Anisidine: Difference between revisions

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Revision as of 15:11, 17 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit Latest revision as of 20:16, 1 November 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,129 edits removed Category:2-Aminophenyl compounds; added Category:4-Aminophenyl compounds using HotCat 
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{{DISPLAYTITLE:''p''-Anisidine}} {{DISPLAYTITLE:''p''-Anisidine}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 396510606
| Watchedfields = changed
⚫ | verifiedrevid = 414442906
| Name = ''p''-Anisidine | Name = ''p''-Anisidine
| ImageFile = 4-Anisidine.png | ImageFileL1 = 4-Anisidine.png
| ImageSize = 100px | ImageSizeL1 = 90px
| ImageAltL1 = Skeletal formula of ''p''-anisidine
| IUPACName = 4-Methoxyaniline
| ImageFileR1 = P-Anisidine 3D ball.png
⚫ | Section1 = {{Chembox Identifiers
| ImageSizeR1 = 110px
⚫ | InChI = 1/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3
| ImageAltR1 = Ball-and-stick model of ''p''-anisidine
⚫ | ChEMBL = 295652
| PIN = 4-Methoxyaniline<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 669 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4 | quote = The names ‘toluidine’, ‘anisidine’, and ‘phenetidine’ for which ''o''-, ''m''-, and ''p''- have been used to distinguish isomers, and ‘xylidine’ for which numerical locants, such as 2,3-, have been used, are no longer recommended, nor are the corresponding prefixes ‘toluidine’, ‘anisidino’, ‘phenetidine’, and ‘xylidino’.}}</ref>
| OtherNames = ''para''-Anisidine; 4-Aminoanisole; ''p''-Aminoanisole
⚫ |Section1={{Chembox Identifiers
⚫ | InChI = 1/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 295652
| ChEBI = 82388
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3 | StdInChI = 1S/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3
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| SMILES = COc1ccc(cc1)N | SMILES = COc1ccc(cc1)N
| CASNo = 104-94-9 | CASNo = 104-94-9
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | EC-number = 203-254-2
| UNII = 575917SNR4
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | EC_number = 203-254-2
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13869414 | ChemSpiderID = 13869414
| KEGG_Ref = {{keggcite|correct|kegg}}
⚫ | UNNumber = 2431
| KEGG = C19326
⚫ }}
| PubChem = 7732
⚫ | Section2 = {{Chembox Properties
| RTECS = BZ5450000
⚫ | Reference = <ref>{{RubberBible62nd|page=C-98}}.</ref>
⚫ | UNNumber = 2431
| Formula = C<sub>7</sub>H<sub>9</sub>NO
⚫ }}
| MolarMass = 123.15 g/mol
⚫ |Section2={{Chembox Properties
| MeltingPt = 57.2 ºC
⚫ | Properties_ref = <ref>{{RubberBible62nd|page=C-98}}</ref>
| BoilingPt = 243 ºC
| Appearance = Light reddish brown solid<ref name=cdc/>
⚫ | Density = 1.071 (57 ºC)
| Odor = Fishy<ref name=cdc/>
⚫ | RefractIndex = 1.5559
| Solubility = soluble | C=7 | H=9 | N=1 | O=1
| MeltingPtC = 56 to 59
⚫ | SolubleOther = soluble in ], ], ], ]
| MeltingPt_notes =
⚫ }}
| BoilingPtC = 243
⚫ | Section7 = {{Chembox Hazards
⚫ | Density = 1.071 (at 57 °C)
| EUIndex = 612-112-00-2
⚫ | RefractIndex = 1.5559
| FlashPt = 122 ºC (252 ºF)
| Solubility = Sparingly soluble<ref name=cdc/>
| Autoignition = 515 ºC (959 ºF)
⚫ | SolubleOther = Soluble in ], ], ], ]
⚫ }}
| Solvent = other solvents
⚫ | Section8 = {{Chembox Related
| VaporPressure = 0.006 mmHg (25&nbsp;°C)<ref name=NIOSH/>
⚫ | OtherCpds = ]<br/>]
| MagSus = -80.56·10<sup>−6</sup> cm<sup>3</sup>/mol
⚫ }}
⚫ }}
⚫ |Section7={{Chembox Hazards
| MainHazards= Carcinogen
| FlashPtC = 122
| AutoignitionPtC = 515
| GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|300|310|330|350|373|400}}<ref>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/p-Anisidine#section=Safety-and-Hazards|title=p-Anisidine safety and hazards|access-date=2022-12-02|website=pubchem.ncbi.nlm.nih.gov}}</ref>
| PPhrases = {{P-phrases|201|202|260|262|264|270|271|273|280|281|284|301+310|302+350|304+340|308+313|310|314|320|321|322|330|361|363|391|403+233|405|501}}
| PEL = TWA 0.5 mg/m<sup>3</sup> <ref name=NIOSH>{{PGCH|0035}}</ref>
| IDLH = 50 mg/m<sup>3</sup><ref name=NIOSH/>
| REL = TWA 0.5 mg/m<sup>3</sup> <ref name=NIOSH/>
| LD50 = 145 mg/kg (rabbit, oral)<ref>p-Anisidine toxicity</ref><br/>130 mg/kg (mouse, oral)<br/>140 mg/kg (rat, oral)<ref name=IDLH>{{IDLH|104949|''p''-Anisidine}}</ref>
| LDLo = 100 mg/kg (mouse, oral)<ref name=IDLH/>
⚫ }}
⚫ |Section8={{Chembox Related
⚫ | OtherCompounds = ]<br/>]
⚫ }}
}} }}


'''''p''-Anisidine''' (or '''''para''-anisidine''') is an organic compound with the formula CH<sub>3</sub>OC<sub>6</sub>H<sub>4</sub>NH<sub>2</sub>. A white solid, commercial samples can appear grey-brown owing to air oxidation. It is one of three isomers of ], ]-containing ]s. It is prepared by reduction of 4-nitroanisole.<ref name=Ullmann>{{cite encyclopedia|last1=Mitchell|first1=Stephen C.|last2=Waring|first2=Rosemary H.|chapter=Aminophenols|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|year=2000|doi=10.1002/14356007.a02_099|isbn=3527306730}}</ref>
'''''p''-Anisidine''', a grey-brown solid, is the least toxic of the three isomers of anisidine (oral LD<sub>50</sub>&nbsp;= 1,400&nbsp;mg/kg) but still causes blood damages upon oral ingestion, inhalation or skin contact. If heated strongly, it may release very toxic fumes of nitrogen oxides.

==Anisidine value==
''p''-Anisidine condenses readily with ] and ] to form ]s, which absorb at 350 nm. This colorimetric reaction is used to test for the presence of oxidation products in fats and oils, an official method for detecting them by the ].<ref name=AOCS>{{cite web |title=AOCS Official Method Cd 18-90 |url=http://www.aocs.org/store/ProductDetail.cfm?ItemNumber=2259 |publisher=American Oil Chemists' Society |access-date=26 February 2013}}</ref> It is particularly good at detecting ] aldehydes, which are the ones that are most likely to generate unacceptable flavors, making it particularly useful in food quality testing.<ref name=Steele>{{cite book |last=Steele |first=Robert |title=Understanding and Measuring the Shelf-Life of Food. Woodhead Publishing in Food Science and Technology Series |year=2004 |publisher=Woodhead Publishing |isbn=1855737329 |page=136 |url=https://books.google.com/books?id=bdnfe_Q5UAMC&pg=PA136}}</ref><ref>{{cite encyclopedia|encyclopedia=Encyclopedia of Food and Health|year=2016|pages=357–364|chapter=Vegetable Oils: Composition and Analysis|author=A.J. Dijkstra|doi=10.1016/B978-0-12-384947-2.00708-X|isbn=9780123849533}}</ref>

==Safety==
''p''-Anisidine is a relatively toxic compound with a ] of 0.5 mg/m<sup>3</sup>.<ref name=cdc>{{cite web |url= https://www.cdc.gov/niosh/docs/81-123/pdfs/0034-rev.pdf |title= Occupational Safety and Health Guideline for Anisidine (''o''-, ''p''-isomers) }}</ref>


==References== ==References==
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*{{PGCH|0035}} *{{PGCH|0035}}


{{DEFAULTSORT:Anisidine-4}} {{DEFAULTSORT:Anisidine}}
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{{amine-stub}}
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