| 56th | Top IARC Group 1 carcinogens |
| 2-Naphthylamine | |
|---|---|
 |
|
| IUPAC name |
2-Aminonaphthalene
|
| Other names | 2-Naphthylamine β-Naphthylamine |
| Identifiers | |
| CAS number | 91-59-8  |
| SMILES |
NC2=CC1=CC=CC=C1C=C2
|
| Properties | |
| Molecular formula | C10H9N |
| Molar mass | 143.19 g/mol |
| Density | 1.061 g/cm3 |
| Melting point |
111-113 °C |
| Boiling point |
306 °C |
| Related compounds | |
| Related compounds | 2-Naphthol |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| Infobox references | |
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 It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by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 amines; it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized. On oxidation it yields ortho-carboxy-hydrocinnamic acid, HO2C•C6H4•CH2•CH2•CO 2H. Numerous sulfonic acids derived from 2-naphthylamine are known. 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.
2-Naphthylamine is found in cigarette smoke and suspected to contribute to the development of bladder cancer.[1]
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.
| 2-Naphthylamine | |
|---|---|
| 2-Aminonaphthalene | |
| Other names 2-Naphthylamine β-Naphthylamine | |
| Identifiers | |
| CAS number | 91-59-8 |
| ChemSpider | 6790 |
| SMILES | c12ccccc1ccc(N)c2
|
| InChI | InChI=1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2
|
| InChI key | JBIJLHTVPXGSAM-UHFFFAOYAA
|
| Properties | |
| Molecular formula | C10H9N |
| Molar mass | 143.19 g/mol |
| Density | 1.061 g/cm3 |
| Melting point |
111-113 °C |
| Boiling point |
306 °C |
| Related compounds | |
| Related compounds | 2-Naphthol |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
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 amines; it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized. On oxidation it yields ortho-carboxy-hydrocinnamic acid, HO2C•C6H4•CH2•CH2•CO2H. Numerous sulfonic acids derived from 2-naphthylamine are known. 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.
2-Naphthylamine is found in cigarette smoke and suspected to contribute to the development of bladder cancer.[1]
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.
   | http://www.emedicine.com/MED/topic2344.htm - Bladder Cancer: eMedicine Urology |
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