719390
2-Pyridylboronic acid MIDA ester
Synonym(s):
2-Pyridinylboronic acid MIDA ester
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About This Item
Empirical Formula (Hill Notation):
C10H11BN2O4
CAS Number:
Molecular Weight:
234.02
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
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
SMILES string
CN1CC(=O)OB(OC(=O)C1)c2ccccn2
InChI key
OEKJACZNFHBYNV-UHFFFAOYSA-N
form
solid
impurities
≤15 wt. % DMSO
storage temp.
2-8°C
Application
MIDA boronates as stable boronic acid surrogates for classically challenging cross-couplings.
Suzuki Cross-Coupling with MIDA Boronates
Suzuki Cross-Coupling with MIDA Boronates
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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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