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Encyclopedia Britannica



SAFRANINE

This article appears in Volume V23, Page 1000 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: SAC-SAR
SAFRANINE , in
chemistry
 , the azonium compounds of symmetrical diamino-phenazine and containing the ring
system
  annexed:-
C(ANY) or \ Cl 1~ C1 I2
They are obtained by the
joint
  oxidation of one molecule of a paradiamine with two molecules of a
primary
  amine; by the condensation of para-aminoazo compounds with
primary
  amines (0. Witt, Ber., 1877, 10, p. 874), and by the action of para-nitrosodialkylanilines with secondary bases such as diphenylmetaphenylenediamine. They are crystalline solids showing a characteristic green metallic lustre; they are readily soluble in water and dye red or
violet
 . They are strong bases and form
stable
  monacid salts. Their alcoholic solution shows a yellow-red fluorescence.
Phenosafranine is not very
stable
  in the free state; its chloride forms green plates. It can be readily diazotized, and the diazonium
salt
  when boiled with alcohol yields aposafranine or benzene induline, C,BH,zN,. F. Kehrmann showed that aposafranine could be diazotized in the presence of cold concentrated sulphuric acid, and the diazonium
salt
  on boiling with alcohol yielded phenylphenazonium salts. Aposafranone, C,H12N20, is formed by
heating
  aposafranine with concentrated hydrochloric acid. These three compounds are perhaps to be represented as ortho- or as paraquinones (see papers by F. Kehrmann, O. Fischer and E. Hepp; R. Nietzki and others, Ber., 1895 et seq.). The " safranine " of commerce is a tolusafranine. The first aniline dye-stuff to be prepared on a manufacturing scale was mauveine, C ,H2,N,C1, which was obtained by Sir W. H.
Perkin
  by
heating
  crude aniline with potassium bichromate and sulphuric acid. It is a N-phenylsafranine (see INDULINES).


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