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698148

Sigma-Aldrich

3-Nitrophenylboronic acid MIDA ester

97%

Synonym(s):

6-Methyl-2-(3-nitrophenyl)-1,3,6,2-dioxazaborocane-4,8-dione

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About This Item

Empirical Formula (Hill Notation):
C11H11BN2O6
CAS Number:
Molecular Weight:
278.03
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

powder

mp

211-215 °C

SMILES string

CN1CC(=O)OB(OC(=O)C1)c2cccc(c2)[N+]([O-])=O

InChI

1S/C11H11BN2O6/c1-13-6-10(15)19-12(20-11(16)7-13)8-3-2-4-9(5-8)14(17)18/h2-5H,6-7H2,1H3

InChI key

COEHPTUYNRXODY-UHFFFAOYSA-N

Application

3-Nitrophenylboronic acid MIDA ester is a stable boronic acid surrogate that can be used as a reagent in the Suzuki-Miyaura cross-coupling reactions to prepare useful building blocks via C-C bond formation. 3-allylnitrobenzene is one of the building blocks prepared from this ester by reacting with allyl bromide in the presence of a palladium catalyst.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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MIDA boronate allylation-synthesis of ibuprofen
Phillips D, et al.,
Royal Society of Chemistry Advances, 10(51), 30624-30630 (2020)

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