Das, S and Alexeev, VL and Sharma, AC and Geib, SJ and Asher, SA
(2003)
Synthesis and crystal structure of 4-amino-3-fluorophenylboronic acid.
Tetrahedron Letters, 44 (42).
7719 - 7722.
ISSN 0040-4039
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Abstract
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.
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