Related articles - What is Pyridine-4-boronic acid?
- Organic boron compounds play an important role in organic chemistry, materials science and biochemistry, and can be used in or....
- Feb 13，2020
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| | Pyridine-4-boronic acid Basic information | | Uses |
| | 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 | | pka | 7.59±0.10(Predicted) | | color | White to Off-White | | BRN | 471944 | | InChI | InChI=1S/C5H6BNO2/c8-6(9)5-1-3-7-4-2-5/h1-4,8-9H | | InChIKey | QLULGIRFKAWHOJ-UHFFFAOYSA-N | | SMILES | C1=NC=CC(B(O)O)=C1 | | CAS DataBase Reference | 1692-15-5(CAS DataBase Reference) |
| | 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.
| | 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 | | Uses | Boronic acid derivatives and their binding affinities with diols. | | Uses | 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
| | Uses | suzuki reaction | | Synthesis | 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). | | 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. |
| | Pyridine-4-boronic acid Preparation Products And Raw materials |
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