2-Naphthylamine

June 2026 changed 477214767 2-Naphthylamine 2-Naphthylamine.PNG skin-invert-image 200 Skeletal formula 2-Naphthylamine-3D-balls.png bg-transparent 200 Ball-and-stick model Naphthalen-2-amine 2-Naphthaleneamine2-Aminonaphthaleneβ-Naphthylamineβ-Aminonaphthalene correct chemspider 6790 correct kegg C02227 1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2 JBIJLHTVPXGSAM-UHFFFAOYAA correct EBI 278164 correct chemspider 1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2 correct chemspider JBIJLHTVPXGSAM-UHFFFAOYSA-N 91-59-8 correct CAS correct EBI 27878 7057 165176 606264 202-080-4 QM2100000 1650 CKR7XL41N4 c12ccccc1ccc(N)c2 10 9 1 1.061 g/cm3 White to red crystals odorless 111 to 113 306 3.92 1 mmHg (107°C) miscible in hot water −98.00·10−6 cm3/mol 3150442 07 08 09 Danger 302 350 411 201 202 264 270 273 281 301+312 308+313 330 391 405 501 2-Naphthol 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 It was formerly used to make azo dyes, but it is a known carcinogen and has largely been replaced by less toxic compounds.Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. 10.1002/14356007.a17_009. 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.y Naphthylamines 19 169 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. 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.Castleman, Barry (1979), Dupont's Record In Business Ethics: Another View, Washington Post, July 15th 1979 Role in disease 2-Naphthylamine is found in cigarette smoke and suspected to contribute to the development of bladder cancer.CDC - NIOSH Pocket Guide to Chemical Hazards 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 Category:IARC Group 1 carcinogens Category:Naphthylamines Category:2-Naphthyl compounds