p-Anisidine
{{DISPLAYTITLE:p-Anisidine}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 414442906
| Name = p-Anisidine
| ImageFileL1 = 4-Anisidine.png
| ImageSizeL1 = 90px
| ImageAltL1 = Skeletal formula of p-anisidine
| ImageFileR1 = P-Anisidine 3D ball.png
| ImageSizeR1 = 110px
| ImageAltR1 = Ball-and-stick model of p-anisidine
| PIN = 4-Methoxyaniline{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | 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’.}}
| 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 = 1S/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BHAAPTBBJKJZER-UHFFFAOYSA-N
| SMILES = COc1ccc(cc1)N
| CASNo = 104-94-9
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 575917SNR4
| EC_number = 203-254-2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13869414
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C19326
| PubChem = 7732
| RTECS = BZ5450000
| UNNumber = 2431
}}
|Section2={{Chembox Properties
| Properties_ref = {{RubberBible62nd|page=C-98}}
| Appearance = Light reddish brown solid
| C=7 | H=9 | N=1 | O=1
| MeltingPtC = 56 to 59
| MeltingPt_notes =
| BoilingPtC = 243
| Density = 1.071 (at 57 °C)
| RefractIndex = 1.5559
| Solubility = Sparingly soluble
| SolubleOther = Soluble in ethanol, diethyl ether, acetone, benzene
| Solvent = other solvents
| VaporPressure = 0.006 mmHg (25 °C)
| MagSus = −80.56·10−6 cm3/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}}{{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}}
| 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/m3 [skin]{{PGCH|0035}}
| LD50 = 145 mg/kg (rabbit, oral)p-Anisidine toxicity
130 mg/kg (mouse, oral)
140 mg/kg (rat, oral){{IDLH|104949|p-Anisidine}}
| LDLo = 100 mg/kg (mouse, oral)
}}
|Section8={{Chembox Related
| OtherCompounds = o-Anisidine
m-Anisidine
}}
}}
p-Anisidine (or para-anisidine) is an organic compound with the formula CH3OC6H4NH2. A white solid, commercial samples can appear grey-brown owing to air oxidation. It is one of three isomers of anisidine, methoxy-containing anilines. It is prepared by reduction of 4-nitroanisole.{{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}}
Anisidine value
p-Anisidine condenses readily with aldehydes and ketones to form Schiff bases, 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 American Oil Chemists' Society.{{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}} It is particularly good at detecting unsaturated aldehydes, which are the ones that are most likely to generate unacceptable flavors, making it particularly useful in food quality testing.{{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}}{{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}}
Safety
p-Anisidine is a relatively toxic compound with a permissible exposure limit of 0.5 mg/m3.{{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) }}
References
{{reflist}}
External links
- {{ICSC|0971|09}}
- {{PGCH|0035}}
{{DEFAULTSORT:Anisidine}}
Category:4-Aminophenyl compounds