Skip to Content
MilliporeSigma
All Photos(3)

Documents

637386

Sigma-Aldrich

6-Chloro-3-pyridinylboronic acid

≥95.0%

Synonym(s):

2-Chloro-5-pyridineboronic acid

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C5H5BClNO2
CAS Number:
444120-91-6
Molecular Weight:
157.36
MDL number:
MFCD03094998
UNSPSC Code:
12352103
PubChem Substance ID:
24882850
NACRES:
NA.22

assay

≥95.0%

form

solid

mp

165 °C (lit.)

SMILES string

OB(O)c1ccc(Cl)nc1

InChI

1S/C5H5BClNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3,9-10H

InChI key

WPAPNCXMYWRTTL-UHFFFAOYSA-N

Application

6-Chloro-3-pyridinylboronic acid can be used:
  • To prepare biologically significant 3-arylcoumarins by reacting with 3-chlorocoumarin through Suzuki reaction.
  • As a substrate in the synthesis of 11-(pyridinylphenyl)steroid with progesterone agonist/antagonist profile.
  • As a substrate in the preparation of α- secondary and tertiary pyridines by the reaction of pyridotriazoles with boronic acids.
  • As a substrate in the palladium-catalyzed α-arylation of saturated cyclic amines and N-methyl amines.

Other Notes

Contains varying amounts of anhydride

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’.

Already Own This Product?

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

Visit the Document Library

Metal-Free Denitrogenative C-C Couplings of Pyridotriazoles with Boronic Acids To Afford α-Secondary and α-Tertiary Pyridines
Dong C, et al.
Organic Letters, 21(11), 4148-4152 (2019)
11-(Pyridinylphenyl) steroids-A new class of mixed-profile progesterone agonists/antagonists
Rewinkel J, et al.
Bioorganic & Medicinal Chemistry, 16(6), 2753-2763 (2008)
Synthesis of 3-arylcoumarins via Suzuki-cross-coupling reactions of 3-chlorocoumarin
Matos MJ, et al.
Tetrahedron Letters, 52(11), 1225-1227 (2011)
α-Arylation of Saturated Azacycles and N-Methylamines via Palladium (II)-catalyzed C (sp3)-H Coupling
Spangler JE, et al.
Journal of the American Chemical Society, 137(37), 11876-11879 (2015)

Articles

Suzuki-Miyaura Cross-Coupling Reagents

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

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