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642622

Sigma-Aldrich

3-Pyridineboronic acid neopentylglycol ester

97%

Synonym(s):

5,5-Dimethyl-2-(3-pyridyl)-1,3,2-dioxaborinane, Pyridine-3-boronic acid neopentylglycol ester

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About This Item

Empirical Formula (Hill Notation):
C10H14BNO2
CAS Number:
845885-86-1
Molecular Weight:
191.03
MDL number:
MFCD03425979
UNSPSC Code:
12352103
PubChem Substance ID:
24883211
NACRES:
NA.22

assay

97%

form

solid

mp

92-96 °C (lit.)

SMILES string

CC1(C)COB(OC1)c2cccnc2

InChI

1S/C10H14BNO2/c1-10(2)7-13-11(14-8-10)9-4-3-5-12-6-9/h3-6H,7-8H2,1-2H3

InChI key

QMEKTOQBDDVVBE-UHFFFAOYSA-N

Application

3-Pyridineboronic acid neopentylglycol ester can be used as a reactant:
  • To synthesize N-alkyl-3-boronopyridinium salts by reacting with corresponding alkyl halides.
  • In the ruthenium-catalyzed diastereoselective C-H bond α-arylation of cyclic amines.
  • To prepare 2-(3-pyridyl)benzoxazole by reacting with benzoxazole via copper-catalyzed oxidative arylation reaction.
  • In the Suzuki-Miyaura cross-coupling reaction.

pictograms

Exclamation mark
GHS07

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nickel/N-Heterocyclic carbene-catalyzed Suzuki-Miyaura type cross-coupling of aryl carbamates
Ohtsuki A, et al.
The Journal of Organic Chemistry, 81(19), 9409-9414 (2016)
sp3 C- H bond arylation directed by amidine protecting group: α-arylation of pyrrolidines and piperidines
Pastine SJ, et al.
Journal of the American Chemical Society, 128(44), 14220-14221 (2006)
Preparation of a series of N-alkyl-3-boronopyridinium halides and study of their stability in the presence of hydrogen peroxide
Karpichev Y, et al.
Central European Journal of Chemistry, 10(4), 1059-1065 (2012)
Copper-Catalyzed Oxidative Arylation of Heteroarenes under Mild Conditions Using Dioxygen as the Sole Oxidant
Yang F, et al.
Chemistry?A European Journal , 17(23), 6321-6325 (2011)

Articles

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

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