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

abstract

• 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.

authors

• Burgess, Kevin

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

publisher

• American Chemical Society (ACS)  Publisher

published in

• Journal of Organic Chemistry  Journal

keywords

• Fluoresceins
• Fluorescent Dyes
• Hydrocarbons, Halogenated
• Molecular Structure
• Stereoisomerism

PubMed Central ID

• 14535816

Digital Object Identifier (DOI)

• 10.1021/jo034724f

start page

• 8264

end page

• 8267

volume

• 68

issue

• 21

URL

• http://dx.doi.org/10.1021/jo034724f