4-Chloro-o-toluidine
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IUPAC name
4-Chloro-2-methylaniline
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| Other names
2-Amino-5-chlorotoluene; 2-Methyl-4-chloroaniline; 4-Chloro-2-toluidine; 5-Chloro-2-aminotoluene; para-Chloro-ortho-toluidine; p-Chloro-o-toluidine
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| Identifiers | |
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3D model (JSmol)
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| Abbreviations | 4-COT |
| ChemSpider | |
| ECHA InfoCard | 100.002.220 |
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PubChem CID
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| Properties | |
| C7H8ClN | |
| Molar mass | 141.60 g·mol−1 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
4-Chloro-o-toluidine (4-COT, 4-chloro-2-methylaniline) is the organic compound with the formula CH3C6H3Cl(NH2). It is a colorless solid. The compound is produced as an intermediate to the pesticide chlordimeform and a precursor to some azo dyes. Production has declined after it was shown to be highly carcinogenic.
It is produced by the chlorination reaction of N-aceyltoluidine followed by deprotection and separation from the 6-chloro isomer. Production of 4-chloro-o-toluidine began in Germany in 1924. In Switzerland, 4-COT and its salts were produced between 1956 and 1976. Production and distribution ceased in 1979 in the US and in 1986 in Germany.
In nature, 4-COT is found in plants and animals as a metabolic product of chlordimeform.
In chronic feeding studies (mice of both sexes), 4-COT induces hemangiosarcomas and hemangioendotheliomas.
4-COT becomes covalently bound to DNA of rats and mice livers.
Inhalation or skin contact with 4-COT produces acute toxic effects, initially appearing as macroscopic or microscopic haematuria. Further symptoms include dysuria, reduced bladder capacity and pain the lower abdomen. Haemorrhagic cystitis is the main symptom of acute toxicity, with methaemoglobinaemia was observed in 50% of poisoning cases.
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