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Synthesis and crystal structure of 4-amino-3-fluorophenylboronic acid

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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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Das, S
Alexeev, VL
Sharma, AC
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Asher, SAasher@pitt.eduASHER
Date: 13 October 2003
Date Type: Publication
Journal or Publication Title: Tetrahedron Letters
Volume: 44
Number: 42
Page Range: 7719 - 7722
DOI or Unique Handle: 10.1016/j.tetlet.2003.08.094
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4039
Date Deposited: 27 Feb 2013 18:47
Last Modified: 16 Feb 2019 15:55
URI: http://d-scholarship.pitt.edu/id/eprint/17378

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