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518786

Sigma-Aldrich

4-Hydroxy-3-methoxyphenylboronic acid pinacol ester

98%

Synonym(s):

2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 4-Hydroxy-3-methoxyphenylboronic acid, pinacol cyclic ester

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About This Item

Empirical Formula (Hill Notation):
C13H19BO4
CAS Number:
Molecular Weight:
250.10
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

assay

98%

mp

105-109 °C (lit.)

SMILES string

COc1cc(ccc1O)B2OC(C)(C)C(C)(C)O2

InChI

1S/C13H19BO4/c1-12(2)13(3,4)18-14(17-12)9-6-7-10(15)11(8-9)16-5/h6-8,15H,1-5H3

InChI key

WFSJROCEOJANPD-UHFFFAOYSA-N

Application

4-Hydroxy-3-methoxyphenylboronic acid pinacol ester can be used as a reactant:
  • In the Suzuki-Miyaura cross-coupling reaction.
  • To prepare ethylidenedihydroindolones as potential neoplastic agents.
  • To synthesize 5,6-dihydropyrrolo[2,1-b]isoquinoline derivatives, which can be utilized as scaffolds to prepare lamellarin analogs via regioselective bromination and Suzuki cross-coupling reactions.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Articles

The synthesis of biaryl compounds via the Suzuki coupling reaction has become more commonplace now that many arylboronic acids are readily available. We are pleased to offer arylboronic acid pinacol esters4 as part of a growing line of products used in the Suzuki coupling reaction.

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available.

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