%0 Journal Article
%@ 0040-4039
%A Das, S
%A Alexeev, VL
%A Sharma, AC
%A Geib, SJ
%A Asher, SA
%D 2003
%F pittir:17378
%J Tetrahedron Letters
%N 42
%P 7719 - 7722
%T Synthesis and crystal structure of 4-amino-3-fluorophenylboronic acid
%U http://d-scholarship-dev.library.pitt.edu/17378/
%V 44
%X 4-Amino-3-fluorophenyl boronic acid has been synthesized from 4-bromo-2-fluoroaniline by protecting the amine group and then carrying out a lithium-bromine exchange, followed by addition of trimethyl borate and then acidic hydrolysis. We obtained a 47% yield. We also measured the X-ray crystal structure. This derivative has a relatively low boronic acid pKa value of 7.8 when acetylated or attached to acrylamide hydrogels. It also contains a pendant amine which facilitates attachment to polymers, for example. We are using this compound to construct glucose sensing materials that operates at the physiological pH of bodily fluids. © 2003 Published by Elsevier Ltd.