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ACRIDINE, C13H9N

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Originally appearing in Volume V01, Page 155 of the 1911 Encyclopedia Britannica.
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ACRIDINE, C13H9N , in See also:chemistry, a heterocyclic See also:ring See also:compound found in crude See also:coal-See also:tar See also:anthracene. It may be separated by shaking out with dilute sulphuric See also:acid, and then precipitating the sulphuric acid See also:solution with See also:potassium bichromate, the resulting acridine bichromate being decomposed by See also:ammonia. It was first isolated in 1890 by C. Graebe and H. See also:Caro (See also:Ann., 1871, 158, p. 265). Many synthetic processes are known for the See also:production of acridine and its derivatives. A. Bernthsen (Ann., 1884, 224, p. 1) condensed diphenylamine with fatty acids, in the presence of See also:zinc chloride. Formic acid yields acridine, and the higher homologues give derivatives substituted at the meso See also:carbon See also:atom, N N +H000HC6H5 /INC6H5-C6H4CI> See also:C6H4 C6H6•NH•C6H6 CHO CH N N L +CH3000H- See also:C6H5/I\C6H5- C6H4<I>C6H4 OCH, C(See also:CH3) Acridine may also be obtained by passing the vapour of phenyl- ortho-toluidine through a red-hot See also:tube (C. Graebe, See also:Bee., 1884, 17, p.

1370); by condensing diphenylamine with See also:

chloroform, in presence of See also:aluminium chloride (0. See also:Fischer, Ber., 1884, 17, p. 102) ; by passing the vapours of orthoaminodiphenylmethane over heated litharge (O. Fischer); by See also:heating salicylic aldehyde with See also:aniline and zinc chloride to 26o° C. (R. Mohlau, Bee., r886, 19, p. 2452); and by distilling acridone over zinc dust (C. Graebe, Ber., 1892, 25, p. 1735). Acridine and its homologues are very See also:stable compounds of feebly basic See also:character. They combine readily with the alkyl iodides to See also:form alkyl acridinium iodides, which are readily trans-formed by the See also:action of alkaline potassium ferricyanide to N-alkyl acridones. Acridine crystallizes in needles which melt at 11o° C.

It is characterized by its irritating action on the skin, and by the See also:

blue See also:fluorescence shown by solutions of its salts. On oxidation with potassium permanganate it yields acridinic acid (See also:quinoline -a-3-dicarboxylic acid) C9H5N(000H)2. Numerous derivatives of acridine are known and may be prepared by methods analogous to those used for the formation of the See also:parent See also:base. For the preparation of the naphthacridines, see F. See also:Ullmann, See also:German See also:Patents 117472, 118439, 127.586, 128754, and also Ber., 1902, 35, pp. 316, 2670. Phenyl-acridine is the parent base of chrysaniline, which is the See also:chief constituent of the dye-stuff phosphine (a bye-product in the manufacture of rosaniline). Chrysaniline (diamino-phenylacridine) forms red-coloured salts,which dye See also:silk and See also:wool a See also:fine yellow; and the solutions of the salts are characterized by their fine yellowish-See also:green fluorescence. It was synthesized by 0. Fischer and G. Koerner (Ber., 1884, 17, p. 203) by condensing ortho-nitrobenzaldehyde with aniline, the resulting ortho-nitro-See also:para-diamino-See also:triphenylmethane being reduced to the corresponding orthoamino compound, which on oxidation yields chrysaniline.

Benzoflavin, an isomer of chrysaniline, is also a dye-stuff, and has been prepared by K. See also:

Oehler (See also:English Patent 9614) from See also:meta-phenylenediamine and See also:benzaldehyde. These substances condense to form tetra-aminotriphenylmethane, which, on heating with acids, loses ammonia and yields diaminodihydrophenylacridine, from which benzoflavin is obtained by oxidation. It is a yellow See also:powder, soluble in hot See also:water. The formulae of these substances are: /N/ N\I INH. H2NI \I/N I/ INH2 /Nc /\/ \/\0/ \/ /\I N H2 Chrysaniline. Benzoflavin.

End of Article: ACRIDINE, C13H9N

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