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

被引：34

作者：

Das, S ^{[1
]}

Alexeev, VL ^{[1
]}

Sharma, AC ^{[1
]}

Geib, SJ ^{[1
]}

Asher, SA ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 42期

基金：

美国国家卫生研究院;

关键词：

4-amino-3-fluorophenylboronic acid; synthesis; crystal structure; X-ray diffraction; glucose sensor; polymerized crystalline colloidal array;

D O I：

10.1016/j.tetlet.2003.08.094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 pK(a) 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. (C) 2003 Published by Elsevier Ltd.

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页码：7719 / 7722

页数：4

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