Russian Journal of Organic Chemistry

, Volume 44, Issue 10, pp 1538–1542 | Cite as

Brominated and iodinated thiofluoresceins

  • V. V. Russkikh
  • E. V. Vasil’ev
  • V. V. Shelkovnikov


Conditions were found for the synthesis of mono-, di-, tri-, and tetrabromo- and -iodo-substituted thiofluoresceins. Iodination and bromination of thiofluorescein with molecular iodine and bromine in 1 N aqueous sodium hydroxide gave mixtures of the corresponding 2,4,5,7-tetra- and 2,4,5-trihalo derivatives in 71/14 (Y = I) and 73/13% yield (Y = Br), respectively. In the reactions of thiofluorescein with bromine in acetic acid and with iodine in methanol at a substrate-to-halogen ratio of 1 : 2, 4,5-dibromo- and 4,5-diiodothiofluoresceins were isolated in 56 and 67% yield. Analogous reactions with equimolar amounts of the reactants produced 59% of 4-bromothiofluorescein and 51% of 4-iodothiofluorescein.


Electronic Absorption Spectrum Aqueous Sodium Hydroxide Molecular Iodine Lactone Form Thioxanthen 
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  1. 1.
    Elcov, A.W., Smirnova, N.P., Ponyaev, A.I., Martinova, W.P., Schutz, R., and Hartmann, H., J. Luminesc., 1990, vol. 47, p. 99.CrossRefGoogle Scholar
  2. 2.
    El’tsov, A.V., Ponyaev, A.I., and Martynova, V.P., Zh. Obshch. Khim., 1992, vol. 62, p. 1626.Google Scholar
  3. 3.
    German Patent no. 636 224, 1936; Chem. Abstr., 1937, vol. 31, p. 872.Google Scholar
  4. 4.
    Apostolova, E.S. and El’tsov, A.V., Zh. Obshch. Khim., 1990, vol. 60, p. 2606.Google Scholar
  5. 5.
    Markuszewski, R. and Diehl, H., Talanta, 1980, vol. 27, p. 937.CrossRefGoogle Scholar
  6. 6.
    Sandin, R.B. and Orvis, R.L., J. Org. Chem., 1958, vol. 23, p. 1234.CrossRefGoogle Scholar
  7. 7.
    Lissitzky, S., Vigne, J., Ruby, Ph., and Fondarai, J., Bull. Soc. Chim. Fr., 1959, p. 389.Google Scholar
  8. 8.
    Evans, L., III, J. Chromatogr. A., 2003, vol. 991, p. 275.CrossRefGoogle Scholar
  9. 9.
    Russkikh, V.V., Konstantinova, A.V., Berezhnaya, V.N., Gerasimova, T.N., and Shelkovnikov, V.V., Russ. J. Org. Chem., 2005, vol. 41, p. 57.CrossRefGoogle Scholar

Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  • V. V. Russkikh
    • 1
  • E. V. Vasil’ev
    • 1
  • V. V. Shelkovnikov
    • 1
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesNovosibirskRussia

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