774650
5-Bromo-2,2′-bithiophene-5-boronic acid MIDA ester
95%
Synonym(s):
2-(5′-Bromo-[2,2′-bithiophen]-5-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
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About This Item
Empirical Formula (Hill Notation):
C13H11BBrNO4S2
CAS Number:
Molecular Weight:
400.08
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
InChI
1S/C13H11BBrNO4S2/c1-16-6-12(17)19-14(20-13(18)7-16)10-4-2-8(21-10)9-3-5-11(15)22-9/h2-5H,6-7H2,1H3
SMILES string
BrC1=CC=C(C2=CC=C(B3OC(CN(C)CC(O3)=O)=O)S2)S1
InChI key
FNDOSCIRFUFXGS-UHFFFAOYSA-N
assay
95%
form
solid
mp
215-219 °C (decomposition)
Application
Protected boronic acid with methylimindodiacetic acid (MIDA) that does not react under standard Suzuki-Miyuara coupling conditions, allowing for selective and iterative cross-coupling sequences. The MIDA boronate also provides prolonged shelf life and stability to typically unstable boronic acid derivatives.
MIDA Boronates
MIDA Boronates
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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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