1692-15-5 Usage
Description
Pyridine-4-boronic acid is a boronic acid derivative that exists as a light orange granular powder. It is a useful building block in crystal engineering and can also act as a catalyst for dehydrative condensation reactions to synthesize amides using carboxylic acid and amines as raw materials. Its derivative, polystyrene-bound 4-pyridineboronic acid, is a valuable catalyst for amidation reactions and esterification of alpha-hydrocarboxylic acids.
Uses
1. Used in Suzuki-Miyaura Coupling Reactions:
Pyridine-4-boronic acid is used as a candidate for Suzuki-Miyaura coupling reactions, particularly as a nitrogen-containing building block to construct heterocyclic compounds with superior biological activities.
2. Used in Pharmaceutical Industry:
Pyridine-4-boronic acid is used as a reagent for palladium-catalyzed Suzuki-Miyaura coupling reactions, which are essential in the synthesis of various pharmaceutical compounds, including HIV-1 protease inhibitors and potential cancer therapeutics such as PDK1 and protein kinase CK2 inhibitors.
3. Used in Chemical Synthesis:
Pyridine-4-boronic acid is used as a catalyst to promote dehydrative condensation reactions, synthesizing amides from carboxylic acids and amines. This application is crucial in the production of various chemical compounds and materials.
4. Used in Catalyst Development:
The derivative of pyridine-4-boronic acid, polystyrene-bound 4-pyridineboronic acid, is used as a catalyst for amidation reactions and esterification of alpha-hydrocarboxylic acids, enhancing the efficiency and selectivity of these processes in the chemical industry.
5. Used in Material Science:
As a building block in crystal engineering, pyridine-4-boronic acid contributes to the development of new materials with unique properties and potential applications in various fields, including electronics, optics, and sensors.
6. Used in Research and Development:
Pyridine-4-boronic acid is employed in research and development for the synthesis of novel compounds and the study of their binding affinities with diols, which can lead to the discovery of new chemical reactions and applications in various industries.
References
http://www.wako-chem.co.jp/english/labchem/product/Org/pyridineboronic/
José J. CamposGaxiola et al. "Pyridineboronic Acids as Useful Building Blocks in Combination with Perchloroplatinate(II) and -(IV) Salts: 1D, 2D, and 3D Hydrogen-Bonded Networks Containing X-H???Cl2Pt? (X = C, N+), B(OH)2???Cl2Pt?, and B(OH)2???(HO)2B Synthons." Crystal Growth & Design 10.7(2010).
Kara, H., A. G. Orpen, and T. J. Podesta. "Pyridine boronic acids as building blocks in crystal engineering." Acta Crystallographica 61.Suppl (2001): C357.
Check Digit Verification of cas no
The CAS Registry Mumber 1692-15-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,9 and 2 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1692-15:
(6*1)+(5*6)+(4*9)+(3*2)+(2*1)+(1*5)=85
85 % 10 = 5
So 1692-15-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H6BNO2.ClH/c8-6(9)5-1-3-7-4-2-5;/h1-4,8-9H;1H
1692-15-5Relevant articles and documents
A molecular box derived from cobaloxime units held together by 4-pyridinylboronic acid residues
Dreos,Nardin,Randaccio,Siega,Tauzher,Vrdoljak
, p. 5536 - 5540 (2001)
The reaction of CH3Co(DH)2H2O with 4-pyridinyl boronic acid in methanol or water affords the dinuclear complexes [MeCo(DH)(DB(OR)(4-Py))]2, with R = Me (2) or H (3), respectively, through reaction of boron with the oxime oxygens of the alkylcobaloxime and coordination of the pyridinyl N to cobalt. The reaction is strongly pH dependent, and the formation of the complexes requires a neutral medium. The complexes have been fully characterized by 1H and 13C NMR spectroscopy, ESI-MS spectrometry, and elemental analysis. The X-ray structure shows that in 2, the pyridinyl groups are facing each other and nearly perpendicular both to the plane of the Co B Co1 B 1 atoms and to the mean equatorial plane, so that the complex may be considered a molecular box. A dimeric arrangement has already been found in the related [MeCo(DH)(DB(OMe)(3-Py))]2 (1) complex, which forms a distorted molecular rectangle [Dreos, R.; Nardin, G.; Randaccio, L.; Tauzher, G.; Vuano, S. Inorg. Chem. 1997, 36, 2463]. The dimerization is possible in both cases, as the conformational freedom of the B bridge compensates for the different position (3- or 4-) of the pyridinyl N donor.
Nitrogen-containing compound, electronic element and electronic device
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Paragraph 0143-0145, (2020/05/01)
The invention provides a nitrogen-containing compound, an electronic component and an electronic device, and relates to the technical field of organic materials, wherein the nitrogen-containing compound is represented by a formula I, X is selected from oxygen and sulfur, R is selected from heterocycloalkyl and heteroaryl, L is selected from a single bond, arylene and heteroarylene, the substituentof R is selected from deuterium, nitro, hydroxyl, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, heterocycloalkyl, alkoxy, aryl silyl and alkyl silyl, and the substituent of L is selected from deuterium, nitro, hydroxyl, alkyl, cycloalkyl, alkenyl, alkynyl, heterocycloalkyl, alkoxy, alkylsilyl, arylsilyl, aryloxy and arylthio. The nitrogen-containing compound disclosed by the invention can reduce the working voltage of an electronic component, improve the efficiency of a device and prolong the service life of the device.
Synthesis of Pyridylanthracenes and Their Reversible Reaction with Singlet Oxygen to Endoperoxides
Fudickar, Werner,Linker, Torsten
, p. 9258 - 9262 (2017/09/11)
The ortho, meta, and para isomers of 9,10-dipyridylanthracene 1 have been synthesized and converted into their endoperoxides 1-O2 upon oxidation with singlet oxygen. The kinetics of this reaction can be controlled by the substitution pattern an
