Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

634492

Sigma-Aldrich

4-Pyridinylboronic acid

90%

Synonym(s):

4-Pyridineboronic acid, 4-Pyridylboronic acid

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

About This Item

Empirical Formula (Hill Notation):
C5H6BNO2
CAS Number:
1692-15-5
Molecular Weight:
122.92
MDL number:
MFCD01074545
UNSPSC Code:
12352103
PubChem Substance ID:
24882629
NACRES:
NA.22

Assay

90%

form

solid

mp

>300 °C (lit.)

storage temp.

−20°C

SMILES string

OB(O)c1ccncc1

InChI

1S/C5H6BNO2/c8-6(9)5-1-3-7-4-2-5/h1-4,8-9H

InChI key

QLULGIRFKAWHOJ-UHFFFAOYSA-N

Related Categories

General description

4-Pyridinylboronic acid is commonly used as a reagent in cross-coupling reactions such as Suzuki-Miyaura cross-coupling.

Application

Reagent used for
  • Palladium-catalyzed Suzuki-Miyaura coupling reactions
  • Ligand-free palladium-catalyzed Suzuki coupling reaction under microwave irradation

Reagent used in Preparation of
  • HIV-1 protease inhibitors
  • Potential cancer threapeutics, such as PDK1 and protein kinase CK2 inhibitors

Other Notes

Contains varying amounts of anhydride

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
MKCQ5422
MKCN5544
MKCK6174
MKCG9894
MKCB1153V

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

Sumin Lee et al.
Organic letters, 14(9), 2238-2241 (2012-04-28)
The kinetic process of key intermediates involved in the electrochemical ring opening of photochromic dithienylcyclopentenes (DTEs) has been observed for the first time, where the electronic nature of the DTEs is an important factor that determines the rate-determining step in
Jorge Cruz-Huerta et al.
Chemical communications (Cambridge, England), 48(35), 4241-4243 (2012-03-23)
The combination of two heteroaromatic boronic acids with pentaerythritol gave self-complementary tectons which were suitable for the generation of 2D and 3D molecular networks.
Sarah J Vella et al.
Beilstein journal of organic chemistry, 14, 1908-1916 (2018-08-17)
A two-station [2]catenane containing a large macrocycle with two different recognition sites, one bis(pyridinium)ethane and one benzylanilinium, as well as a smaller DB24C8 ring was synthesized and characterized. 1H NMR spectroscopy showed that the DB24C8 ring can shuttle between the
Jin-Tao Yu et al.
Organic & biomolecular chemistry, 10(7), 1359-1364 (2011-12-20)
An efficient palladium-catalyzed Suzuki-Miyaura coupling method involving the reaction between CTV-Br(3) and a variety of aryl and heteroaryl boronic acids in the presence of indolyl phosphane ligands has been developed. This reaction procedure provided a series of C(3)-symmetric aryl-extended rigid
Ligand-free, PdCl2(PPh3)2-catalyzed, microwave-assisted Suzuki coupling of 1-chloro-3-phenylisoquinoline in the synthesis of diversified 1,3-disubstituted isoquinolines
Prabakaran, K.; Nawaz Khan, F.; Jin, J. S.
Research on Chemical Intermediates, 38, 337-346 (2012)
View All Related Papers

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

Suzuki-Miyaura Cross-Coupling Reagents

The Suzuki-Miyaura cross-coupling reaction is an important and extensively used reaction in organic chemistry with applications in polymer science and in the fine chemicals 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