| Revision as of 14:07, 13 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: {{cascite}} StdInChI StdInChIKey SMILES.← Previous edit |
Latest revision as of 20:15, 1 November 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits +Category:Anisidines; ±Category:Anilines→Category:2-Aminophenyl compounds using HotCat |
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{{DISPLAYTITLE:''o''-Anisidine}} |
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{{DISPLAYTITLE:''o''-Anisidine}} |
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{{chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 310454918 |
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| Watchedfields = changed |
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| verifiedrevid = 433349433 |
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| Name = ''o''-Anisidine |
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| Name = ''o''-Anisidine |
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| ImageFile = 2-Anisidine.png |
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| ImageFileL1 = 2-Anisidine.png |
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| ImageSize = 120px |
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| ImageSizeL1 = 120px |
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| ImageAltL1 = Skeletal formula of ''o''-anisidine |
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| IUPACName = 2-Methoxyaniline |
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| ImageFileR1 = O-Anisidine 3D ball.png |
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| Section1 = {{Chembox Identifiers |
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| ImageSizeR1 = 120 |
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| InChI = 1/C7H9NO/c1-9-7-5-3-2-4-6(7)8/h2-5H,8H2,1H3 |
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| ImageAltR1 = Ball-and-stick model of the ''o''-anisidine molecule |
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| SMILES = Nc1ccccc1OC |
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| PIN = 2-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> |
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| StdInChI = 1S/C7H9NO/c1-9-7-5-3-2-4-6(7)8/h2-5H,8H2,1H3 |
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| OtherNames = ''ortho''-Anisidine<br>2-Anisidine<br />''ortho''-Aminoanisole<br />''o''-Methoxyaniline<br />2-Methoxy-1-aminobenzene<br />2-Methoxyphenylamine |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C7H9NO/c1-9-7-5-3-2-4-6(7)8/h2-5H,8H2,1H3 |
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| SMILES = Nc1ccccc1OC |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C7H9NO/c1-9-7-5-3-2-4-6(7)8/h2-5H,8H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEBI = 82288 |
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| StdInChIKey = VMPITZXILSNTON-UHFFFAOYSA-N |
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| StdInChIKey = VMPITZXILSNTON-UHFFFAOYSA-N |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1612004 |
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| CASNo = 90-04-0 |
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| CASNo = 90-04-0 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| EC-number = 201-963-1 |
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| EC_number = 201-963-1 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13860775 |
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| ChemSpiderID = 13860775 |
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| UNNumber = 2431 |
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| UNNumber = 2431 |
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}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| Section2 = {{Chembox Properties |
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| KEGG = C19191 |
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| Reference = <ref>{{RubberBible62nd|page=C-98}}.</ref> |
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| PubChem = 7000 |
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| Formula = C<sub>7</sub>H<sub>9</sub>NO |
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| RTECS = BZ5410000 |
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| MolarMass = 123.15 g/mol |
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| Density = 1.092 g/ml |
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| UNII = NUX042F201 |
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}} |
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| MeltingPt = 6.2 °C |
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|Section2={{Chembox Properties |
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| BoilingPt = 224 °C |
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| Properties_ref = <ref>{{RubberBible62nd|page=C-98}}</ref> |
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| Density = 1.0923 g/cm<sup>3</sup> |
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| Solubility = 1.5 g/100 ml |
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| C=7 | H=9 | N=1 | O=1 |
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| Appearance = Yellow liquid, turns brown upon exposure to air |
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| SolubleOther = soluble in ], ], ], ] |
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| MeltingPtC = 6.2 |
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| BoilingPtC = 224 |
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| Section7 = {{Chembox Hazards |
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| Density = 1.0923 g/cm<sup>3</sup> |
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| EUClass = Toxic ('''T''')<br/>{{Carc2}}<br/>{{Muta3}} |
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| Solubility = 1.5 g/100 ml |
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| EUIndex = 612-035-00-4 |
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| SolubleOther = soluble in ], ], ], ] |
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| NFPA-H = 2 |
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| MagSus = -80.44·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| NFPA-F = 1 |
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}} |
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| NFPA-R = 0 |
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|Section7={{Chembox Hazards |
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| RPhrases = {{R45}}, {{R23/24/25}}, {{R68}} |
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| NFPA-H = 2 |
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| SPhrases = {{S53}}, {{S45}} |
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| NFPA-F = 1 |
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| FlashPt = 118 °C (open cup) |
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| NFPA-R = 0 |
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| Autoignition = 415 °C |
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| FlashPtC = 118 |
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| FlashPt_notes = (open cup) |
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| Section8 = {{Chembox Related |
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| AutoignitionPtC = 415 |
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| OtherCpds = ]<br/>] |
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| GHSPictograms = {{GHS06}}{{GHS08}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|311|331|341|350}} |
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| PPhrases = {{P-phrases|201|202|261|264|270|271|280|281|301+310|302+352|304+340|308+313|311|312|321|322|330|361|363|403+233|405|501}} |
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| PEL = TWA 0.5 mg/m<sup>3</sup> <ref name=NIOSH>{{PGCH|0034}}</ref> |
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| MainHazards = potential occupational carcinogen<ref name=NIOSH/> |
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| IDLH = 50 mg/m<sup>3</sup><ref name=NIOSH/> |
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| REL = : Ca TWA 0.5 mg/m<sup>3</sup> <ref name=NIOSH/> |
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| LD50 = 2000 mg/kg (rat, oral)<br/> 1400 mg/kg (mouse, oral)<br/>870 mg/kg (rabbit, oral)<ref>{{IDLH|90040|''o''-Anisidine}}</ref> |
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|Section8={{Chembox Related |
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| OtherCompounds = ]<br/>] |
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'''''o''-Anisidine''' ('''2-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 colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing ] derivative. |
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'''''o''-Anisidine''' is a yellow liquid with melting point -1 to 5 °C and density 1.09 g/cm³. The vapor pressure is 0.05 mbar at 20 °C but increases greatly with temperature. It has an aromatic smell and is well absorbed by inhalation, oral ingestion and skin contact. 2-Anisidine is a very toxic agent that causes blood, enzyme and nerve damage with ] and the danger of suffocation. The agent is an experimental ] and is strongly suspected to be also a human carcinogen. 2-Anisidine has dangerous pollutant properties for water. |
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==Production and use== |
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It is prepared via methanolysis of 2-chloronitrobenzene:<ref name=Booth>{{cite encyclopedia|author=Gerald Booth|chapter=Nitro Compounds, Aromatic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2007|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a17_411|isbn=978-3527306732}}</ref> |
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:NaOCH<sub>3</sub> + ClC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> → CH<sub>3</sub>OC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> + NaCl |
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The resulting ] is reduced to ''o''-anisidine. |
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''o''-Anisidine is used in the manufacture of dyes. It is nitrated to give 4-nitroanisidine. It is also a precursor to ]. |
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One special use is as a ] indicator. An acid solution of ''o''-anisidine is ] by adding a sodium nitrite solution. This mixture is applied to the wood and by reaction with ] in the heartwood a reddish brown ] is formed. |
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:] is an ] produced from ''o''-anisidine]]{{clear-left}} |
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==Safety and environmental aspects== |
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''o''-Anisidine is a dangerous pollutant from the production of dyes. It is listed as RCRA ], with the code K181.<ref>{{Cite web | url=http://www.epa.gov/osw/hazard/wastetypes/wasteid/dyes/index.htm | title=Hazardous Waste| date=2015-07-23}}</ref> The International Agency for Research on Cancer (IARC) has classified ''o''-anisidine as a Group 2B, possible human carcinogen.<ref>{{Cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/o-anisidine#section=Top |title = ''o''-Anisidine}}</ref> |
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==References== |
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==References== |
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*{{PGCH|0034}} |
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*{{PGCH|0034}} |
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{{DEFAULTSORT:Anisidine-2}} |
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{{DEFAULTSORT:Anisidine, o-}} |
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