1692-15-5

Basic information

• Product Name: Pyridine-4-boronic acid
• Synonyms: PYRIDYL-4-BORONIC ACID;PYRIDINE-4-BORONIC ACID;PYRIDINE-4-BORONIC ACID HYDRATE;PYRIDIN-4-YLBORONIC ACID;PYRIDIN-4-YL-4-BORONIC ACID;RARECHEM AH PB 0240;TIMTEC-BB SBB004280;AKOS BRN-0273
• CAS NO: 1692-15-5
• Molecular Formula: C₅H₆BNO₂
• Molecular Weight: 122.91764
• EINECS: 1312995-182-4
• Product Categories: blocks;BoronicAcids;Pyridines;Miscellaneous;Boronic Acids & Esters;Boronic acids;Heterocyclic Compounds;Boronic acid;Organoborons;Pyridine;B (Classes of Boron Compounds);Aromatics;Boron Derivatives;Heterocycles;Boronic Acids & Esters;Boronic Acids;Boronic Acids and Derivatives;Heteroaryl;Boronate Ester;Potassium Trifluoroborate
• Mol File: 1692-15-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 308.782 °C at 760 mmHg
• Flash Point: 140.547 °C
• Appearance: light orange granular powder
• Density: 1.23 g/cm³
• Vapor Pressure: 6.52E-05mmHg at 25°C
• Storage Temp.: 0-6°C
• Solubility: Aqueous Acid (Slightly), Water (Slightly)
• PKA: 7.59±0.10(Predicted)
• BRN: 471944
• CAS DataBase Reference: Pyridine-4-boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine-4-boronic acid(1692-15-5)
• EPA Substance Registry System: Pyridine-4-boronic acid(1692-15-5)

Safety Data

• Hazard Codes: Xn,Xi,C,F
• Statements: 36/37/38-22-34-11
• Safety Statements: 22-24/25-36/37/39-26-45-16
• WGK Germany: 3
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 1692-15-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1692-15-5 differently. You can refer to the following data:
1. Pyridine-4-boronic acid can be used as a candidate for Suzuki-Miyaura coupling reaction. Especially, as a N-containing building blocks, pyridine-4-boronic acid was employed to construct some heterocyclic compounds with superior biological activities.
2. suzuki reaction
3. Reagent used forPalladium-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
4. Boronic acid derivatives and their binding affinities with diols.

Description

Pyridine-4-boronic acid is a kind of boronic acid derivative. It is useful building blocks in crystal engineering. It can also be used as a catalyst to act as a dehydrative condensation agent to synthesize amides using carboxylic acid and amines as raw materials. Its derivative, polystyrene-bound 4-pyridineboronic acid, is a useful catalyst for amidation reaction and esterification of alpha-hydrocarboxylic acids.

Chemical Properties

light orange granular powder

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.

InChI:InChI=1/C5H6BNO2.ClH/c8-6(9)5-1-3-7-4-2-5;/h1-4,8-9H;1H

Upstream product

• 121-43-7 Trimethyl borate 
• 19524-06-2 4-bromopyridine hydrochloride 
• 1120-87-2 4-bromopyridin 
• 7732-18-5 water 
• 5419-55-6 Triisopropyl borate 
• 497-19-8 sodium carbonate 

Downstream Products

• 954123-92-3 tert-butyl 4-((2-methoxy-5-(pyridin-4-yl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate 
• 873667-02-8 (R)-[1-(4-(4-pyridylbenzyl))pyrrolidin-3-yl]dimethylamine 
• 850868-79-0 1,2-bis{2-[4-(4-pyridyl)phenylmethoxy]ethoxy}ethane 
• 21308-82-7 4-(thiophen-3-yl)-pyridine 
• 939-23-1 p-phenylpyridine 
• 4282-45-5 4-(4-nitrophenyl)pyridine 
• 144397-70-6 4-(pyridin-4-yl)benzonitrile 
• 79739-33-6 5-(4-pyridyl)pyridin-2-amine 
• 93844-98-5 2-(pyridin-4-yl)pyrazine 
• 581-47-5 4-(2-pyridyl)pyridine 
• 887616-78-6 1-benzenesulfonyl-6-bromo-3-pyridin-4-yl-1H-indole 

Relevant articles and documents

A molecular box derived from cobaloxime units held together by 4-pyridinylboronic acid residues

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

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

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