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| Names | |
|---|---|
| Preferred IUPAC name Naphthalen-2-ylamine | |
| Other names 2-Naphthaleneamine 2-Aminonaphthalene β-Naphthylamine β-Aminonaphthalene | |
| Identifiers | |
| |
3D model (JSmol) | |
| 606264 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| ECHA InfoCard | 100.001.892 |
| EC Number |
|
| 165176 | |
| KEGG |
|
| RTECS number |
|
| UNII | |
| UN number | 1650 |
| |
| |
| Properties | |
| C10H9N | |
| Molar mass | 143.189 g·mol−1 |
| Appearance | White to red crystals[1] |
| Odor | odorless[1] |
| Density | 1.061 g/cm3 |
| Melting point | 111 to 113 °C (232 to 235 °F; 384 to 386 K) |
| Boiling point | 306 °C (583 °F; 579 K) |
| miscible in hot water[1] | |
| Vapor pressure | 1 mmHg (107°C)[1] |
| Acidity (pKa) | 3.92 |
| −98.00·10−6 cm3/mol | |
| Hazards | |
| GHS labelling: | |
   | |
| Danger | |
| H302,H350,H411 | |
| P201,P202,P264,P270,P273,P281,P301+P312,P308+P313,P330,P391,P405,P501 | |
| Flash point | 157 °C; 315 °F; 430 K |
| Related compounds | |
Related compounds | 2-Naphthol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
2-Naphthylamine or2-aminonaphthalene is one of twoisomeric 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 It was formerly used to makeazo dyes, but it is a knowncarcinogen and has largely been replaced by less toxic compounds.[2]
2-Naphthylamine is prepared by heating2-naphthol withammoniumzinc chloride to 200-210 °C, theBucherer reaction. Itsacetyl derivative can be obtained by heating 2-naphthol withammoniumacetate to 270-280 °C.[3]
It gives no color withiron(III) chloride. When reduced bysodium in boilingamyl alcohol solution, it forms tetrahydro-3-naphthylamine, which exhibits the properties of thealiphaticamines in that it is stronglyalkaline in reaction, has anammoniacal odor and cannot bediazotized. Onoxidation, it yieldsortho-carboxy-hydrocinnamic acid, HO2CC6H4CH2CH2CO2H.[3]
Numeroussulfonic acid derivatives of 2-naphthylamine are used in commerce, such as precursors todyes.[2] Owing to the carcinogenicity of the amine, these derivatives are mainly prepared by amination of the correspondingnaphthols. Of them, the δ-acid and Bronner's acid are of more value technically, since they combine withortho-tetrazoditolyl to produce fine red dye-stuffs.[3]
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.[4]
2-Naphthylamine is found incigarette smoke and suspected to contribute to the development ofbladder cancer.[5]
It is activated in the liver but quickly deactivated by conjugation toglucuronic acid. In the bladder,glucuronidase re-activates it by deconjugation, which leads to the development of bladder cancer.
One or more of the preceding sentences incorporates text from a publication now in thepublic domain: Chisholm, Hugh, ed. (1911). "Naphthylamines".Encyclopædia Britannica. Vol. 19 (11th ed.). Cambridge University Press. p. 169.
