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Merck
CN

637386

6-Chloro-3-pyridinylboronic acid

≥95.0%

Synonym(s):

2-Chloro-5-pyridineboronic acid

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About This Item

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

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InChI

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

SMILES string

OB(O)c1ccc(Cl)nc1

InChI key

WPAPNCXMYWRTTL-UHFFFAOYSA-N

assay

≥95.0%

form

solid

mp

165 °C (lit.)

functional group

chloro

Quality Level

100

Related Categories

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
60396EMV
SHBB0663V
43798MJ
28696JJ
09703MH

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Synthesis of 3-arylcoumarins via Suzuki-cross-coupling reactions of 3-chlorocoumarin
Matos MJ, et al.
Tetrahedron Letters, 52(11), 1225-1227 (2011)
11-(Pyridinylphenyl) steroids-A new class of mixed-profile progesterone agonists/antagonists
Rewinkel J, et al.
Bioorganic & Medicinal Chemistry, 16(6), 2753-2763 (2008)
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)
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.

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