Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

100

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBS7070V
MKBS0346V
MKBN2252V
MKBD9552V
MKBC9724

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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)

Articles

Suzuki–Miyaura Coupling Reagents

This brochure contains a comprehensive selection of boronic acids, boronic acid esters, diboron esters, and transition-metal catalysts useful for the Suzuki–Miyaura coupling reaction

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service