All Photos(3)
Synonym(s):
4-Pyridineboronic acid, 4-Pyridylboronic acid
Empirical Formula (Hill Notation):
C5H6BNO2
CAS Number:
Molecular Weight:
122.92
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
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
Reagent used in Preparation of
- 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
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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)
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)
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
Articles
Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.
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