Syntheses of regioisomerically pure 5- or 6-halogenated fluoresceins. Academic Article uri icon


  • Three routes to regioisomerically pure 5- and 6-iodofluoresceins or 5- and 6-bromofluoresceins are described. The first, shown in Scheme 1, involves diazotization/iodination of the corresponding aminofluoresceins. In the second approach (Scheme 2) a mixture of regioisomeric fluoresceins was prepared, and the 5-bromo isomers were isolated as the ring closed diacetates 9b and 11 by fractional crystallization. Scheme 3 shows an approach to sulfonic acid derivatives 3 and 4 of 5-iodofluorescein. This is the most convenient procedure of the three, and it is particularly useful as sulfofluoresceins have more favorable water solubility characteristics than fluoresceins that lack the sulfonic acid group.

published proceedings

  • J Org Chem

altmetric score

  • 3

author list (cited authors)

  • Jiao, G., Han, J. W., & Burgess, K.

citation count

  • 29

complete list of authors

  • Jiao, Guan-Sheng||Han, Jin Wook||Burgess, Kevin

publication date

  • October 2003