4 0 obj 0000274534 00000 n 0000266652 00000 n [6], Aniline has been implicated as one possible cause of forest dieback. 0000219783 00000 n 0000219223 00000 n 0000273258 00000 n 0000203466 00000 n 0000211876 00000 n 0000264795 00000 n 0000316055 00000 n 0000246948 00000 n Aniline hydrochloride forms large colourless tables, which become greenish on exposure; it is the "aniline salt" of commerce. 0000292192 00000 n 0000314673 00000 n 0000204612 00000 n 0000210736 00000 n 0000207652 00000 n 0000285935 00000 n 0000279812 00000 n 0000277862 00000 n Safety Information. 0000293610 00000 n 0000262624 00000 n 0000276891 00000 n 0000252526 00000 n 0000329084 00000 n 0000236273 00000 n 0000258459 00000 n 0000239056 00000 n 0000259466 00000 n 0000230130 00000 n 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. Hypochlorous acid gives para-amino phenol and para-amino diphenylamine (E. Barnberger, Ber., 1898, 31, p. 1522). 2005 Sep 15;158(3):196-212. 0000281229 00000 n 0000244267 00000 n 0000236961 00000 n 0000210180 00000 n 0000289835 00000 n In addition to dyestuffs, it is a starting-product for the manufacture of many drugs, such as antipyrine, antifebrin, &c. Aniline is manufactured by reducing nitrobenzene with iron and hydrochloric acid and steam-distilling the product. 0000212325 00000 n 0000223706 00000 n 0000324733 00000 n 0000292470 00000 n 0000326667 00000 n 0000255184 00000 n 0000233877 00000 n Aniline and its ring-substituted derivatives react with nitrous acid to form diazonium salts. Gerhard Domagk identified as an antibacterial a red azo dye, introduced in 1935 as the first antibacterial drug, prontosil, soon found at Pasteur Institute to be a prodrug degraded in vivo into sulfanilamide – a colorless intermediate for many, highly colorfast azo dyes – already with an expired patent, synthesized in 1908 in Vienna by the researcher Paul Gelmo for his doctoral research. * Definitions are provided on page 5. [6], In commerce, three brands of aniline are distinguished: aniline oil for blue, which is pure aniline; aniline oil for red, a mixture of equimolecular quantities of aniline and ortho- and para-toluidines; and aniline oil for safranine, which contains aniline and ortho-toluidine and is obtained from the distillate (échappés) of the fuchsine fusion. 0000282059 00000 n 0000293779 00000 n 0000316740 00000 n 0000274397 00000 n It is used to stain neural RNA blue in the Nissl stain. 0000252252 00000 n Eb'�V��Ԥ�]I��Ώ�l��Z�Ť�,r,Y��>�p�U1����XZdA��T�+p����UU��}�+�9�$�hk� ����7B|YEA$��D�|SB��@o)�2�_���2��[�B3c+,�*�H�I��'x*��G8�AINA��9w�J/�u�H�!���x����ƘB���� (��� 0000067373 00000 n 0000298600 00000 n 0000235247 00000 n 0000208791 00000 n 0000127365 00000 n 0000237305 00000 n h� s�'$ƊM� 0000294114 00000 n 0000314262 00000 n 0000234393 00000 n 0000317323 00000 n Copyright © 2018 ITA all rights reserved. 0000323637 00000 n 0000280818 00000 n 0000288453 00000 n 0000215121 00000 n 0000205574 00000 n 0000286076 00000 n [24], In 1856, while trying to synthesise quinine, von Hofmann's student William Henry Perkin discovered mauveine and went into industry producing the first commercial synthetic dye. 0000199960 00000 n 0000238302 00000 n Like other amines, aniline is a base (pKaH = 4.6) and nucleophile, although it is a weaker base and poorer nucleophile than structurally similar aliphatic amines. Aniline is a weak base and forms salts with the mineral acids. 0000291499 00000 n 0000301763 00000 n 0000296057 00000 n [, Mathews JM, De Costa KS: Absorption, metabolism, and disposition of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v., and dermal administration. 0000201628 00000 n It is a liquid at room temperature. 0000251700 00000 n 0000285794 00000 n 0000286358 00000 n Traditionally, the weak basicity of aniline is attributed to a combination of inductive effect from the more electronegative sp2 carbon and resonance effects, as the lone pair on the nitrogen is partially delocalized into the pi system of the benzene ring. 0000217895 00000 n 0000208293 00000 n 0000259744 00000 n 0000253665 00000 n 0000213437 00000 n 0000303451 00000 n It is also dense, and can be stored for extended periods. It ignites readily, burning with a smoky flame characteristic of aromatic compounds.[6]. 0000210317 00000 n 0000270668 00000 n 0000316603 00000 n 0000274812 00000 n 0000320270 00000 n 0000225073 00000 n 0000322815 00000 n Int J Legal Med. 0000202965 00000 n [, Gan J, Skipper PL, Gago-Dominguez M, Arakawa K, Ross RK, Yu MC, Tannenbaum SR: Alkylaniline-hemoglobin adducts and risk of non-smoking-related bladder cancer. They are of great importance in the colour industry. 0000301904 00000 n 0000304591 00000 n Aniline is an organic compound with the formula C6H5NH2. 0000329946 00000 n [, Kuo HM, Ho HJ, Chao PD, Chung JG: Quercetin glucuronides inhibited 2-aminofluorene acetylation in human acute myeloid HL-60 leukemia cells. 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.