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
Pricing and availability is not currently available.

Quality Level

100

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.[1]

Application

Reagent used for
  • Palladium-catalyzed Suzuki-Miyaura coupling reactions[2]
  • Ligand-free palladium-catalyzed Suzuki coupling reaction under microwave irradation[3]

Reagent used in Preparation of
  • HIV-1 protease inhibitors[4]
  • Potential cancer threapeutics, such as PDK1 and protein kinase CK2 inhibitors[5][6]

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
MKCW6384
MKCT9387
MKCS8678
MKCQ5422
MKCN5544

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

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)
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
One-pot approach to N-quinolyl 3?/4?-biaryl carboxamides by microwave-assisted Suzuki--Miyaura coupling and N-boc deprotection
ZY Huang, et al.
The Journal of Organic Chemistry, 81, 9647-9657 (2016)
View All Related Papers

Articles

Suzuki-Miyaura Cross-Coupling Reagents

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

Suzuki-Miyaura Cross-Coupling Reagents

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

Suzuki-Miyaura Cross-Coupling Reagents

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

Suzuki-Miyaura Cross-Coupling Reagents

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

Questions

Reviews

No rating value

Active Filters

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