2-Naphthylamine
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Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox HazardsTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Yesno| Template:Longitem | Template:Unbulleted list |
| Template:Longitem | 606264 |
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| Template:Longitem | 165176 |
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| UN number | 1650 |
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| Template:Longitem | Template:Chembox Elements/molecular formula |
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| Appearance | White to red crystals[1] |
| Odor | odorless[1] |
| Density | 1.061 g/cm3 |
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| Vapor pressure | 1 mmHg (107°C)[1] |
| Acidity (pKa) | 3.92 |
| Template:Longitem | −98.00·10−6 cm3/mol |
| Template:Longitem | 2-Naphthol |
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2-Naphthylamine or 2-aminonaphthalene is one of two isomeric 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 It was formerly used to make azo dyes, but it is a known carcinogen and has largely been replaced by less toxic compounds.[2]
Preparation
2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C, the Bucherer reaction. Its acetyl derivative can be obtained by heating 2-naphthol with ammonium acetate to 270-280 °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 amines in that it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized.
On oxidation, it yields ortho-carboxy-hydrocinnamic acid, HO2CC6H4CH2CH2CO2H.
Numerous sulfonic acid derivatives of 2-naphthylamine are used in commerce, such as precursors to dyes.[2] Owing to the carcinogenicity of the amine, these derivatives are mainly prepared by amination of the corresponding naphthols. 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.[3]
Role in disease
2-Naphthylamine is found in cigarette smoke and suspected to contribute to the development of bladder cancer.[4]
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
References
- ↑ a b c d Cite error: Script error: No such module "Namespace detect".Script error: No such module "Namespace detect".
- ↑ a b Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. Script error: No such module "CS1 identifiers"..
- ↑ Castleman, Barry (1979), Dupont's Record In Business Ethics: Another View, Washington Post, July 15th 1979
- ↑ CDC - NIOSH Pocket Guide to Chemical Hazards