| Revision as of 16:42, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 474844537 of page 1-Naphthylamine for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 01:49, 13 November 2024 edit Mdewman6 (talk | contribs)Extended confirmed users, Page movers, New page reviewers, Pending changes reviewers, Rollbackers21,717 edits no such thing as 1-naphthoquinone; the correction is at least analogous to aniline |
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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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| verifiedrevid = 443257246 |
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| verifiedrevid = 477208220 |
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| Name = 1-Naphthylamine |
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| Name = 1-Naphthylamine |
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| ImageFile_Ref = {{chemboximage|changed|??}} |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = 1-Naphthylamine.png |
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| ImageFile = 1-Naphthylamine.png |
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| ImageSize = 150 |
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| ImageSize = 150 |
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| ImageName = Skeletal formula |
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| ImageName = Skeletal formula |
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| ImageFile1 = 1-Naphthylamine-3D-balls.png |
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| ImageFile1 = 1-Naphthylamine-3D-balls.png |
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| ImageSize1 = 180 |
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| ImageSize1 = 180 |
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| ImageName1 = Ball-and-stick model |
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| ImageName1 = Ball-and-stick model |
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| PIN = Naphthalen-1-amine |
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| IUPACName = 1-Aminonaphthalene |
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| OtherNames = 1-Naphthylamine<br />α-Naphthylamine |
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| OtherNames = (Naphthalen-1-yl)amine<br />1-Naphthylamine<br />α-Naphthylamine<br />1-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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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 50450 |
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| ChEBI = 50450 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 134-32-7 |
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| CASNo = 134-32-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 8640 |
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| UNII = 9753I242R5 |
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| SMILES = c1cccc2cccc(N)c12 |
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| PubChem = 8640 |
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| SMILES = Nc1c2ccccc2ccc1 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>9</sub>N |
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| Formula = C<sub>10</sub>H<sub>9</sub>N |
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| Appearance = Colorless crystals (reddish-purple in air)<ref name=PGCH/> |
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| MolarMass = 143.19 g/mol |
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| Odor = ]-like<ref name=PGCH/> |
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| Density = 1.114 g/cm³ |
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| MolarMass = 143.19 g/mol |
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| MeltingPt = 47–50 °C |
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| Density = 1.114 g/cm<sup>3</sup> |
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| BoilingPt = 301 °C |
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| MeltingPtC = 47 to 50 |
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| MeltingPt_notes = |
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| BoilingPtC = 301 |
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| BoilingPt_notes = |
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| VaporPressure = 1 mmHg (104°C)<ref name=PGCH/> |
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| Solubility = 0.002% (20°C)<ref name=PGCH/> |
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| MagSus = {{Plainlist| |
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* -98.8·10<sup>−6</sup> cm<sup>3</sup>/mol |
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* -127.6·10<sup>−6</sup> cm<sup>3</sup>/mol (HCl salt) |
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|Section3={{Chembox Hazards |
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| ExternalSDS = |
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| FlashPtF = 315 |
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| FlashPt_ref = <ref name=PGCH>{{PGCH|0441}}</ref> |
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| Section2 = {{Chembox Related |
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|Section4={{Chembox Related |
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| OtherCpds = ]<br>]<br>]<br>]<br>] |
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| OtherCompounds = ]<br>]<br>]<br>]<br>] |
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'''1-Naphthylamine''' is an ] ] derived from ]. It can cause bladder cancer (transitional cell carcinoma). It ]s in colorless needles which melt at 50 °C. It possesses a disagreeable odor, ]s readily, and turns brown on exposure to air. It is the precursor to a variety of dyes.<ref name=Ullmann>{{cite encyclopedia|author=Gerald Booth|title=Naphthalene Derivatives|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a17_009|isbn=9783527303854 }}.</ref> |
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==Preparation and reactions== |
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It can be prepared by ] 1-nitronaphthalene with ] and ] followed by ].<ref name=Ullmann/> |
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]s, such as ], give a blue ] with solutions of its ]s. ] converts it into ]. ] in boiling ] |
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reduces the unsubstituted ring, giving tetrahydro-1-naphthylamine. This tetrahydro compound yields ] when ]d by ]. |
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At 200 °C in sulfuric acid, it converts to ]. |
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==Use in dyes== |
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The ] are used for the preparation of ]. These compounds possess the important property of dyeing unmordanted ]. |
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An important derivative is ] (1-aminonaphthalene-4-sulfonic acid), which is produced by heating 1-naphthylamine and ] to 170–180 °C in the presence of crystallized ]. It forms small needles, very sparingly soluble in water. Upon treatment with the bis(diazonium) derivative of benzidine, 1-aminonaphthalene-4-sulfonic acid gives ]. |
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==Safety== |
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It is listed as one of the 13 carcinogens covered by the OSHA General Industry Standards.<ref></ref> |
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==See also== |
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*Used in preparation of ]. |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Naphthylamine, 1-}} |
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] |
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] |
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] |