View source for 2-Naphthylamine

{{chembox
| Watchedfields = changed
| verifiedrevid = 271676936
|   Name = 2-Naphthylamine
|   ImageFile = 2-Naphthylamine.PNG
|   ImageSize = 200
|   ImageName = Skeletal formula
|   ImageFile1 = 2-Naphthylamine-3D-balls.png
|   ImageSize1 = 200
|   ImageName1 = Ball-and-stick model
|   IUPACName = 2-Aminonaphthalene
|   OtherNames = 2-Naphthylamine<br />β-Naphthylamine
| Section1 = {{Chembox Identifiers
|   CASNo = 91-59-8
|    CASNo_Ref = {{cascite}}
|   SMILES = NC2=CC1=CC=CC=C1C=C2
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>10</sub>H<sub>9</sub>N
|   MolarMass = 143.19 g/mol
|   Density = 1.061 g/cm<sup>3</sup>
|   MeltingPt = 111-113 °C
|   BoilingPt = 306 °C
  }}
| Section3 = {{Chembox Related
|   OtherCpds = [[2-Naphthol]]
  }}
}}

'''2-Naphthylamine''' is an [[aromatic]] [[amine]]. It is used to make [[azo dyes]]. It is a known human [[carcinogen]] and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-[[naphthol]] with [[ammonium]] [[zinc chloride]] to 200-210 °C; or in the form of its [[acetyl]] derivative by heating 2-naphthol with [[ammonium]] [[acetate]] to 270-280 °C. It forms odorless, colorless plates which melt at 111-112 °C. It gives no color with [[ferric chloride]]. When reduced by [[sodium]] in boiling [[amyl alcohol]] solution it forms alicyclic tetrahydro-3-naphthylamine, which has most of the properties of the [[aliphatic compound|aliphatic]] [[amine]]s; it is strongly [[alkaline]] in reaction, has an [[ammonia]]cal odor and cannot be [[diazo]]tized. On [[oxidation]] it yields ''ortho''-carboxy-hydrocinnamic acid, HO<sub>2</sub>C•C<sub>6</sub>H<sub>4</sub>•CH<sub>2</sub>•CH<sub>2</sub>•CO<sub>2</sub>H. Numerous [[sulfonic acid]]s
derived from 2-naphthylamine are known.<!-- 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 these, the δ-acid and Bronner's acid are of more value technically, since they combine with ''ortho''-tetrazoditolyl to produce fine red dye-stuffs.

==Role in disease==
2-Naphthylamine is found in [[cigarette]] smoke and suspected to contribute to the development of [[bladder cancer]].<ref>Steinberg GD, Kim HL. Bladder Cancer. eMedicine.com. URL: [http://www.emedicine.com/MED/topic2344.htm http://www.emedicine.com/MED/topic2344.htm]. Accessed on: May 9, 2007.</ref> 

It is activated in the liver but quickly deactivated by conjugation to [[glucuronic acid]]. In the bladder, [[glucuronidase]] re-activates it by deconjugation, which leads to the development of bladder cancer.

==References==
<references/>

==See also==
*[[Naphthalene]]
*[[Naphthol]]
*[[1-Naphthylamine]]
*[[1,8-Bis(dimethylamino)naphthalene]]

{{DEFAULTSORT:Naphthylamine, 2-}}
[[Category:Aromatic amines]]
[[Category:IARC Group 1 carcinogens]]
[[Category:Naphthalenes]]

[[de:2-Naphthylamin]]
[[nl:2-naftylamine]]
[[pt:2-Naftilamina]]
[[Category:2Fix]]