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Pyridine-4-boronic acid

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CAS:1692-15-5
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Products Intro: Product Name:pyridin-4-ylboronic acid
CAS:1692-15-5
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Pyridine-4-boronic acid manufacturers

  • 3-Pyridylboronic acid
  • 3-Pyridylboronic acid pictures
  • $35.00/ kg
  • 2023-10-28
  • CAS:1692-15-5
  • Min. Order: 1kg
  • Purity: 99%
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Related articles

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Pyridine-4-boronic acid Basic information
Uses
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:1692-15-5
MF:C5H6BNO2
MW:122.92
EINECS:671-679-4
Product Categories:Heterocyclic Compounds;B (Classes of Boron Compounds);blocks;BoronicAcids;Pyridines;Boronic acid;Organoborons;Pyridine;Miscellaneous;Boronic Acids & Esters;Boronic acids;Aromatics;Boron Derivatives;Heterocycles;Boronic Acids & Esters;Boronic Acids;Boronic Acids and Derivatives;Heteroaryl;Boronate Ester;Potassium Trifluoroborate
Mol File:1692-15-5.mol
Pyridine-4-boronic acid Structure
Pyridine-4-boronic acid Chemical Properties
Melting point >300 °C (lit.)
Boiling point 308.8±34.0 °C(Predicted)
density 1.22±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility Aqueous Acid (Slightly), Water (Slightly)
form Solid
pka7.59±0.10(Predicted)
color White to Off-White
BRN 471944
InChIInChI=1S/C5H6BNO2/c8-6(9)5-1-3-7-4-2-5/h1-4,8-9H
InChIKeyQLULGIRFKAWHOJ-UHFFFAOYSA-N
SMILESC1=NC=CC(B(O)O)=C1
CAS DataBase Reference1692-15-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi,C,F
Risk Statements 36/37/38-22-34-11
Safety Statements 22-24/25-36/37/39-26-45-16
WGK Germany 3
Hazard Note Irritant
HazardClass IRRITANT, KEEP COLD
HS Code 29339900
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Pyridine-4-boronic acid Usage And Synthesis
Uses

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.

DescriptionPyridine-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 Propertieslight orange granular powder
Usessuzuki reaction
UsesReagent 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
UsesBoronic acid derivatives and their binding affinities with diols.
Synthesis
4-Bromopyridine

1120-87-2

Trimethyl borate

121-43-7

Water

7732-18-5

Pyridine-4-boronic acid

1692-15-5

Under argon protection, 4-bromopyridine (1.5 g, 10 mmol) was placed in a 200 mL Schlenk flask and 40 mL of anhydrous deoxytetrahydrofuran was added. After cooling the reaction mixture to -78 °C, 5 mL (2.2 M, 11 mmol) of n-butyllithium solution was slowly added dropwise and the reaction was maintained at this temperature for 1 hour. Subsequently, 4 mL of trimethyl borate was added and the reaction continued at -78 °C for 1 hour. Upon completion of the reaction, the mixture was slowly warmed to room temperature and stirred overnight. The reaction was quenched with 2 mol/L hydrochloric acid solution and purified by recrystallization from hexane to give pyridine-4-boronic acid hydrochloride (0.8 g, 65% yield).

Referenceshttp://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.
Tag:Pyridine-4-boronic acid(1692-15-5) Related Product Information
4-Pyridineboronic acid pinacol ester Boric acid 4-Methylpyridine Chromium picolinate Zinc borate 3-Pyridylboronic acid Sulfasalazine Methyl propyl carbonate (+/-)-NICOTINE 3-Pyridylacetic acid hydrochloride 2-Pyridinecarboxaldehyde Pyridine-2-carbonyl chloride hydrochloride 2-(Hydroxymethyl)pyridine ISONICOTINOYL CHLORIDE HYDROCHLORIDE 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-PYRIDINEMETHANOL HYDROCHLORIDE Pyridine hydrochloride Pyridine hydrobromide

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