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| | 2-Methylpyridine-4-boronic acid pinacol ester Basic information |
| | 2-Methylpyridine-4-boronic acid pinacol ester Chemical Properties |
| Melting point | 66-71°C | | Boiling point | 315.9±30.0 °C(Predicted) | | density | 1.02 | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | solubility | soluble in Methanol | | form | powder to crystal | | pka | 5.11±0.10(Predicted) | | color | White to Almost white | | InChI | 1S/C12H18BNO2/c1-9-8-10(6-7-14-9)13-15-11(2,3)12(4,5)16-13/h6-8H,1-5H3 | | InChIKey | MBTULFIFECUURA-UHFFFAOYSA-N | | SMILES | Cc1cc(ccn1)B2OC(C)(C)C(C)(C)O2 |
| Hazard Codes | Xi | | Risk Statements | 37/38-41 | | Safety Statements | 26-39 | | WGK Germany | WGK 3 | | HS Code | 2933399990 | | Storage Class | 11 - Combustible Solids |
| | 2-Methylpyridine-4-boronic acid pinacol ester Usage And Synthesis |
| Synthesis | The general procedure for the synthesis of 2-methyl-4-pyridylboronic acid pinacol ester from 4-bromo-2-methylpyridine (0.500 g, 2.906 mmol) and pinacol ester of bis(diphenylphosphine) (0.812 g, 3.997 mmol) is as follows: in an inert atmosphere, 4-bromo-2-methylpyridine, pinacol ester of bis(boronic acid), potassium acetate (0.854 g, 8.720 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.021 g, 0.029 mmol) were dissolved in degassed 1,4-dioxane (5 mL) in a 50 mL sealed tube. The reaction mixture was stirred at 80 °C for 4 hours. Upon completion of the reaction, the solvent was removed by rotary evaporation and the crude product was purified by silica gel column chromatography (eluent: ethyl acetate/ether = 30:70) to afford 2-methyl-4-pyridinylboronic acid pinacol ester (0.250 g, 39% yield) as an off-white solid. m/z 220.1 [M + H]+ was shown by LCMS analysis. | | References | [1] Patent: WO2014/111871, 2014, A1. Location in patent: Page/Page column 199
[2] Patent: WO2004/14913, 2004, A2. Location in patent: Page 82
[3] Patent: US2011/190269, 2011, A1. Location in patent: Page/Page column 36
[4] Patent: WO2011/92272, 2011, A1. Location in patent: Page/Page column 73
[5] Patent: WO2011/119518, 2011, A1. Location in patent: Page/Page column 47-48 |
| | 2-Methylpyridine-4-boronic acid pinacol ester Preparation Products And Raw materials |
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