Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2-Naphthylamine: Difference between pages

| Watchedfields = changed

| verifiedrevid = 477214767

| 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

| PIN = Naphthalen-2-amine

| OtherNames = (Naphthalen-2-yl)amine<br>2-Naphthylamine<br>β-Naphthylamine

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| CASNo_Ref = {{cascite|correct|CAS}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| PubChem = 7057

| Gmelin = 165176

| Beilstein = 606264

| EINECS = 202-080-4

| RTECS = QM2100000

| UNNumber = 1650

| UNII = CKR7XL41N4

| C=10|H=9|N=1

| Density = 1.061 g/cm³

| Appearance = White to red crystals<ref name=PGCH/>

| Odor = odorless<ref name=PGCH/>

| MeltingPtC = 111 to 113

| BoilingPtC = 306

| pKa = 3.92

| VaporPressure = 1 mmHg (107°C)<ref name=PGCH/>

| Solubility = miscible in hot water<ref name=PGCH/>

| MagSus = -98.00·10⁻⁶ cm³/mol

| Section3 = {{Chembox Hazards

| FlashPtF = 315<ref name=PGCH>{{PGCH|0442}}</ref>

| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|302|350|411}}

| PPhrases = {{P-phrases|201|202|264|270|273|281|301+312|308+313|330|391|405|501}}

}}

| Section4= {{Chembox Related

| OtherCompounds = [[2-Naphthol]]

'''2-Naphthylamine''' is one of two [[isomer]]ic aminonaphthalenes, compounds with the formula C₁₀H₇NH₂. It is a colorless solid, but samples take on a reddish color in air because of oxidation. It was formerly used to make [[azo dye]]s, but it is a known [[carcinogen]] and has largely been replaced by less toxic compounds.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>

==Preparation==

2-Naphthylamine is prepared by heating [[2-naphthol]] with [[ammonium]] [[zinc chloride]] to 200-210&nbsp;°C, the [[Bucherer reaction]]. Its [[acetyl]] derivative can be obtained by heating 2-naphthol with [[ammonium]] [[acetate]] to 270-280&nbsp;°C.

==Reactions==

It gives no color with [[iron(III) chloride]]. When reduced by [[sodium]] in boiling [[amyl alcohol]] solution, it forms tetrahydro-3-naphthylamine, which exhibits the properties of the [[aliphatic compound|aliphatic]] [[amine]]s in that it is strongly [[alkaline]] in reaction, has an [[ammonia]]cal odor and cannot be [[diazo]]tized.

On [[oxidation]], it yields ''ortho''-carboxy-hydrocinnamic acid, HO₂CC₆H₄CH₂CH₂CO₂H.

Numerous [[sulfonic acid]] derivatives of 2-naphthylamine are used in commerce, such as precursors to [[dye]]s.<ref name=Ullmann/> Owing to the carcinogenicity of the amine, these derivatives are mainly prepared by amination of the corresponding [[naphthol]]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.

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>

==Role in disease==

2-Naphthylamine is found in [[cigarette]] smoke and suspected to contribute to the development of [[bladder cancer]].<ref>[https://www.cdc.gov/niosh/npg/npgd0442.html CDC - NIOSH Pocket Guide to Chemical Hazards]</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.

==See also==

*[[Naphthalene]]

*[[Naphthol]]

*[[1-Naphthylamine]]

*[[1,8-Bis(dimethylamino)naphthalene]]

==References==

<references/>

{{DEFAULTSORT:Naphthylamine, 2-}}

[[Category:IARC Group 1 carcinogens]]

[[Category:Naphthylamines]]

[[Category:2-Naphthyl compounds]]