5043 Aniline Aniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th century. Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. In 1834, Friedrich Runge isolated from coal tar a substance which produced a beautiful blue color on treatment with chloride of lime; this he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit, dark-blue. 62-53-3 6115 C6H7N -6 °C 245 C 36 mg/mL at 25 °C Toxic by ingestion and a skin and eye irritant. Aniline induces lipid peroxidation and protein oxidation in the spleen and that oxidative stress plays a role in the splenic toxicity of aniline. The hematopoietic system is the primary target of aniline insult in rats which is characterized by methemoglobinemia, hemolysis, and hemolytic anemia and by the development of splenic hyperplasia, siderosis, fibrosis, a variety of sarcomas, and, most commonly, fibrosarcomas on prolonged exposure. Many of the characteristics of splenotoxicity in rats, such as hyperplasia, hyperpigmentation, and/or formation of highly malignant tumors such as fibrosarcomas, are not restricted to aniline exposure, but also occur when animals are exposed to substituted anilines such as chloroaniline. Studies with aniline hydrochloride in rats indicate an association between erythrocyte damage and the severity of the splenotoxicity. Since one of the major functions of the spleen is to remove damaged erythrocytes, aniline-damaged erythrocytes would be expected to be scavenged by the spleen, especially by phagocytes. The deposition and subsequent breakdown of damaged erythrocytes will not only release aniline and/or its metabolites, but, most importantly, will also result in accumulation of iron in the spleen which may catalyze the generation of tissue-damaging oxygen radicals which can subsequently cause oxidation of biomolecules and result in lipid peroxidation and protein oxidation. It is also possible that during the scavenging of damaged erythrocytes, the splenic phagocytes, especially macrophages themselves, can become activated and release reactive oxygen species (ROS) which could further contribute to the oxidation of biomolecules leading to tissue injury. (A15460) 3, not classifiable as to its carcinogenicity to humans. (L135) Aniline-induced splenic toxicity is characterized by hemorrhage, capsular hyperplasia, fibrosis, and a variety of sarcomas in rats. 2014-10-14T21:19:36Z 2014-12-24T20:27:01Z http://en.wikipedia.org/wiki/Aniline C00292 17296 34-DICHLOROANILINE C023650 DB06728 ANL true NC1=CC=CC=C1 C6H7N InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 InChIKey=PAYRUJLWNCNPSJ-UHFFFAOYSA-N 93.1265 93.057849229 Endogenous Liquid 0.9 HMDB03012 5889 <p>Michel Dury, &#8220;Method for preparing 2-trifluoro-methoxy-aniline.&#8221; U.S. Patent US6121492, issued 0000.</p>