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774650

Sigma-Aldrich

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:
1104636-79-4
Molecular Weight:
400.08
MDL number:
MFCD26405982
UNSPSC Code:
12352103
PubChem Substance ID:
329767704
NACRES:
NA.22

Assay

95%

form

solid

mp

215-219 °C (decomposition)

SMILES string

BrC1=CC=C(C2=CC=C(B3OC(CN(C)CC(O3)=O)=O)S2)S1

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

InChI key

FNDOSCIRFUFXGS-UHFFFAOYSA-N

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

774650-BULK:
774650-25G:
774650-5G:
774650-1G:
774650-VAR:

Certificates of Analysis (COA)

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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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