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Merck
CN

719390

Sigma-Aldrich

2-吡啶基硼酸甲基亚氨基二乙酸酯

别名:

2-Pyridinylboronic acid MIDA ester

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About This Item

经验公式(希尔记法):
C10H11BN2O4
分子量:
234.02
MDL编号:
UNSPSC代码:
12352103
PubChem化学物质编号:
NACRES:
NA.22

形式

solid

杂质

≤15 wt. % DMSO

储存温度

2-8°C

SMILES字符串

CN1CC(=O)OB(OC(=O)C1)c2ccccn2

InChI

1S/C10H11BN2O4/c1-13-6-9(14)16-11(17-10(15)7-13)8-4-2-3-5-12-8/h2-5H,6-7H2,1H3

InChI key

OEKJACZNFHBYNV-UHFFFAOYSA-N

应用

2-Pyridinylboronic acid MIDA ester represents the first and only example of an air-stable 2-pyridinyl boronate. This stable boronic acid surrogate is a powerful cross coupling partner, useful in the synthesis of pharmaceuticals, natural products, and complex molecules.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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Graham R Dick et al.
Organic letters, 12(10), 2314-2317 (2010-05-15)
A wide range of 2-pyridyl and other difficult-to-access heterocyclic N-methyliminodiacetic acid boronates can be readily prepared from the corresponding bromides via a new method involving direct transligation of 2-heterocyclic trialkoxyborate salts with N-methyliminodiacetic acid (MIDA) at elevated temperatures.
David M Knapp et al.
Journal of the American Chemical Society, 131(20), 6961-6963 (2009-05-02)
Many boronic acids, including 2-heterocyclic, vinyl, and cyclopropyl derivatives, are inherently unstable, which can limit their benchtop storage and/or efficient cross-coupling. We herein report the first general solution to this problem: in situ slow release of unstable boronic acids from

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