FLUORENE ([alpha]-diphenylene methane), C13H10 or (C6H4)2CH2, a hydrocarbon found in coal-tar. It is obtained from the higher boiling fractions, after separation of naphthalene and anthracene, by fractional distillation, the portion boiling between 290-340° C. being taken. The fluorene is separated from this by placing it in a freezing mixture, and is then redistilled or crystallized from glacial acetic acid, or purified by means of its picrate. It may be prepared by distilling diphenylene ketone over zinc dust, or by heating it with hydriodic acid and phosphorus to 150-160° C.; and also by passing the vapour of diphenyl methane through a red hot tube. It crystallizes in colourless plates, possessing a violet fluorescence, melting at 112-113° and boiling at 293-295° C. By oxidation with chromic acid in glacial acetic acid solution, it is converted into diphenylene ketone (C6H4)2·CO; whilst on heating with hydriodic acid and phosphorus to 250-260° C. it gives a hydro derivative of composition C18H22.
FLUORESCEIN, or RESORCIN-PHTHALEIN, C20H12O5, in chemistry, a compound discovered in 1876 by A. v. Baeyer by the condensation of phthalic anhydride with resorcin at 195-200° C. (_Ann._, 1876, 183, p. 1). The two reacting substances are either heated alone or with zinc chloride for some hours, and the melt obtained is boiled out with water, washed by dilute alcohol, extracted by means of sodium hydrate, and the solution so obtained is precipitated by an acid. The precipitate is well washed with water and then dried. By repeating this process two or three times, the fluorescein may be obtained in a very pure condition. It forms a yellow amorphous powder, insoluble in water but soluble in alcohol, and crystallizing from the alcoholic solution in small dark red nodules. It is readily soluble in solutions of the caustic alkalis, the solution being of a dark red colour and showing (especially when largely diluted with water) a brilliant green fluorescence. It was so named on account of this last character. By brominating fluorescein in glacial acetic acid solution, _eosin_ (tetrabromfluorescein) is obtained, the same compound being formed by heating 3.5-dibrom-2.4-dioxybenzoylbenzoic acid above its melting point (R. Meyer, _Ber._, 1895, 28, p. 1576). It crystallizes from alcohol in yellowish red needles, and dyes silk, wool, and mordanted cotton a fine pink colour. When heated with caustic alkalis it yields dibromresorcin and dibrommonoresorcin-phthalein. The corresponding iodo compound is known as _erythrosin_. Fluorescein is readily nitrated, yielding a di- or tetra-nitro compound according to conditions. The entrance of the negative nitro group into the molecule weakens the central pyrone ring in the fluorescein nucleus and the di-and tetra-nitro compounds readily yield hydrates (see J.T. Hewitt and B.W. Perkins, _Jour. Chem. Soc._, 1900, p. 1326). By the action of ammonia or amines the di-nitro fluoresceins are converted into yellow dyestuffs (F. Reverdin, _Ber_., 1897, 30, p. 332). Other dyestuffs obtained from fluorescein are safrosine or eosin scarlet (dibromdinitrofluorescein) and rose Bengal (tetraiodotetrachlorfluorescein).