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637386

Sigma-Aldrich

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:
Molecular Weight:
157.36
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥95.0%

form

solid

mp

165 °C (lit.)

functional group

chloro

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

Signal Word

Warning

Hazard Statements

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

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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 reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

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

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

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

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