| Revision as of 17:28, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465264988 of page 2-Naphthylamine for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 00:48, 13 November 2024 edit Mdewman6 (talk | contribs)Extended confirmed users, Page movers, New page reviewers, Pending changes reviewers, Rollbackers21,661 edits update alt names |
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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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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 457319089 |
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| verifiedrevid = 477214767 |
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| Name = 2-Naphthylamine |
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| Name = 2-Naphthylamine |
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| ImageFile = 2-Naphthylamine.PNG |
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| ImageFile = 2-Naphthylamine.PNG |
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| ImageSize = 200 |
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| ImageSize = 200 |
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| ImageName = Skeletal formula |
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| ImageName = Skeletal formula |
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| ImageFile1 = 2-Naphthylamine-3D-balls.png |
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| ImageFile1 = 2-Naphthylamine-3D-balls.png |
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| ImageSize1 = 200 |
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| ImageSize1 = 200 |
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| ImageName1 = Ball-and-stick model |
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| ImageName1 = Ball-and-stick model |
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| PIN = Naphthalen-2-ylamine |
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| IUPACName = 2-Aminonaphthalene |
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| OtherNames = 2-Naphthylamine<br />β-Naphthylamine |
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| OtherNames = 2-Naphthaleneamine<br>2-Aminonaphthalene<br>β-Naphthylamine<br>β-Aminonaphthalene |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6790 |
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| ChemSpiderID = 6790 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChI = 1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2 |
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| InChI = 1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2 |
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| InChIKey = JBIJLHTVPXGSAM-UHFFFAOYAA |
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| InChIKey = JBIJLHTVPXGSAM-UHFFFAOYAA |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 278164 |
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| ChEMBL = 278164 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2 |
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| StdInChI = 1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = JBIJLHTVPXGSAM-UHFFFAOYSA-N |
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| StdInChIKey = JBIJLHTVPXGSAM-UHFFFAOYSA-N |
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| CASNo = 91-59-8 |
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| CASNo = 91-59-8 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 27878 |
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| ChEBI = 27878 |
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| PubChem = 7057 |
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| Gmelin = 165176 |
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| Beilstein = 606264 |
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| EINECS = 202-080-4 |
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| RTECS = QM2100000 |
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| UNNumber = 1650 |
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| UNII = CKR7XL41N4 |
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| SMILES = c12ccccc1ccc(N)c2 |
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| SMILES = c12ccccc1ccc(N)c2 |
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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=10|H=9|N=1 |
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| Formula = C<sub>10</sub>H<sub>9</sub>N |
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| MolarMass = 143.19 g/mol |
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| Density = 1.061 g/cm<sup>3</sup> |
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| Appearance = White to red crystals<ref name=PGCH/> |
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| Density = 1.061 g/cm<sup>3</sup> |
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| Odor = odorless<ref name=PGCH/> |
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| MeltingPt = 111-113 °C |
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| MeltingPtC = 111 to 113 |
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| BoilingPt = 306 °C |
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| BoilingPtC = 306 |
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| pKa = 3.92 |
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| VaporPressure = 1 mmHg (107°C)<ref name=PGCH/> |
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| Solubility = miscible in hot water<ref name=PGCH/> |
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| MagSus = -98.00·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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| Section3 = {{Chembox Related |
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| Section3 = {{Chembox Hazards |
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| FlashPtF = 315<ref name=PGCH>{{PGCH|0442}}</ref> |
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| OtherCpds = ] |
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| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|302|350|411}} |
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| PPhrases = {{P-phrases|201|202|264|270|273|281|301+312|308+313|330|391|405|501}} |
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}} |
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| Section4= {{Chembox Related |
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| OtherCompounds = ] |
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}} |
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}} |
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}} |
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}} |
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'''2-Naphthylamine''' or '''2-aminonaphthalene''' is one of two ]ic aminonaphthalenes, compounds with the formula C<sub>10</sub>H<sub>7</sub>NH<sub>2</sub>. It is a colorless solid, but samples take on a reddish color in air because of oxidation. It was formerly used to make ]s, but it is a known ] and has largely been replaced by less toxic compounds.<ref name=Ullmann>Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a17_009}}.</ref> |
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==Preparation== |
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2-Naphthylamine is prepared by heating ] with ] ] to 200-210 °C, the ]. Its ] derivative can be obtained by heating 2-naphthol with ] ] to 270-280 °C. |
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==Reactions== |
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It gives no color with ]. When reduced by ] in boiling ] solution, it forms tetrahydro-3-naphthylamine, which exhibits the properties of the ] ]s in that it is strongly ] in reaction, has an ]cal odor and cannot be ]tized. |
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On ], it yields ''ortho''-carboxy-hydrocinnamic acid, HO<sub>2</sub>CC<sub>6</sub>H<sub>4</sub>CH<sub>2</sub>CH<sub>2</sub>CO<sub>2</sub>H. |
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Numerous ] derivatives of 2-naphthylamine are used in commerce, such as precursors to ]s.<ref name=Ullmann/> Owing to the carcinogenicity of the amine, these derivatives are mainly prepared by amination of the corresponding ]s.<!-- the more important of which are the 28 or Badische, the 25 or Dahl, the 27 or, and the 26 or Bronner's acid.--> Of them, the δ-acid and Bronner's acid are of more value technically, since they combine with ''ortho''-tetrazoditolyl to produce fine red dye-stuffs. |
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2-Naphthylamine was previously used as a dye precursor and rubber antioxidant in the 1930s, 40s and 50s. Dupont stopped using it in the 1970s.<ref>Castleman, Barry (1979), Dupont's Record In Business Ethics: Another View, Washington Post, July 15th 1979</ref> |
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==Role in disease== |
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2-Naphthylamine is found in ] smoke and suspected to contribute to the development of ].<ref></ref> |
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It is activated in the liver but quickly deactivated by conjugation to ]. In the bladder, ] re-activates it by deconjugation, which leads to the development of bladder cancer. |
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==See also== |
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*] |
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*] |
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==References== |
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<references/> |
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{{DEFAULTSORT:Naphthylamine, 2-}} |
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] |
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] |
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] |