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634492

Sigma-Aldrich

4-Pyridinylboronic acid

90%

Synonym(s):

4-Pyridineboronic acid, 4-Pyridylboronic acid

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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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)
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
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)
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.
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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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