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| | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Basic information |
| Product Name: | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | | Synonyms: | 3-Pyridineboronic acid pinacol ester
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;3-Pyridineboronic acid pinacol ester 97%;3-PYRIDYLBORONIC ACID PINACOL ESTER;AKOS BRN-1142;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE;2-(3-PYRIDYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;PYRIDIN-3-YLBORONIC ACID PINACOL ESTER;PYRIDINE-3-BORONIC ACID, PINACOL ESTER | | CAS: | 329214-79-1 | | MF: | C11H16BNO2 | | MW: | 205.06 | | EINECS: | | | Product Categories: | ps;B (Classes of Boron Compounds);Boronic Acids Esters;Boronic acid | | Mol File: | 329214-79-1.mol |  |
| | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical Properties |
| Melting point | 102-104.4 °C(lit.) | | Boiling point | 300.9±15.0 °C(Predicted) | | density | 1.03±0.1 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | soluble in Acetone | | pka | 5.22±0.12(Predicted) | | form | Crystalline Powder | | color | White | | Water Solubility | Insoluble | | InChI | InChI=1S/C11H16BNO2/c1-10(2)11(3,4)15-12(14-10)9-6-5-7-13-8-9/h5-8H,1-4H3 | | InChIKey | XEMDFESAXKSEGI-UHFFFAOYSA-N | | SMILES | C1=NC=CC=C1B1OC(C)(C)C(C)(C)O1 | | CAS DataBase Reference | 329214-79-1(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29333990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Usage And Synthesis |
| Chemical Properties | white crystalline powder | | Uses | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine is an organoborane compound used in the preparation of of polyazatriaryl ligands by sequential borylation/Suzuki-Miyaura coupling. 3-Pyridineboronic Acid Pinacol E ster is used in the preparation of pyrrolo[2,3-b]pyridine derivatives as kinase modulators. | | Uses | 3-Pyridineboronic Acid Pinacol Ester is an organoborane compound used in the preparation of polyazatriaryl ligands by sequential borylation/Suzuki-Miyaura coupling. 3-Pyridineboronic Acid Pinacol Ester is used in the preparation of pyrrolo[2,3-b]pyridine derivatives as kinase modulators. | | Synthesis | In a nitrogen-protected glove box, a benzene solution of silica-3p-TPP ([P] content 0.11 mmol/g, 45.5 mg, 0.005 mmol P, 1 mol% P), anhydrous degassed benzene (0.8 mL), and [PdCl(η3-cinnamyl)]2 (0.65 mg, 0.00125 mmol, 0.5 mol% Pd) (0.2 mL) was added sequentially to an oven-dried 10 mL glass tube pre-fitted with a magnetic stirrer. After stirring for 5 min, KOAc (147 mg, 1.5 mmol), bis(pinacolato)diboron (2,140 mg, 0.55 mmol) and 3-chloropyridine (63.3 mg, 0.50 mmol) were added sequentially. The reaction tube was sealed with a screw cap and then removed from the glove box, and the reaction was stirred at 25°C for 10 hours. After completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad (eluting with Et2O) and the filtrate was concentrated under reduced pressure. To the residue was added the internal standard 1,1,2,2-tetrachloroethane, and the yield of the product 3-pyridineboronic acid pinacol ester was 95% as determined by 1H NMR. The crude product was purified by silica gel column chromatography to afford the target compound 3-pyridineboronic acid pinacol ester (87.0 mg, 0.40 mmol, 80% yield). | | References | [1] ChemCatChem, 2014, vol. 6, # 5, p. 1340 - 1348
[2] RSC Advances, 2018, vol. 8, # 25, p. 13643 - 13648
[3] Angewandte Chemie - International Edition, 2007, vol. 46, # 28, p. 5359 - 5363
[4] Chemistry Letters, 2014, vol. 43, # 5, p. 584 - 586
[5] Patent: WO2010/110782, 2010, A1. Location in patent: Page/Page column 46-47 |
| | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Preparation Products And Raw materials |
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