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| | 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester Basic information |
| Product Name: | 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester | | Synonyms: | 1-BENZYL- 4-PYRAZOLEBORONIC ACID PINACOL ESTER;1-Benzyl-4-pyrazole boronic acid pinacol ester, 1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole,97%;1-benzyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyra;1H-Pyrazole, 1-(phenylMethyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;1-(PhenylMethyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, {[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}benzene;1-benzyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | | CAS: | 761446-45-1 | | MF: | C16H21BN2O2 | | MW: | 284.16 | | EINECS: | 671-685-7 | | Product Categories: | API intermediates | | Mol File: | 761446-45-1.mol |  |
| | 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester Chemical Properties |
| Melting point | 86-90 °C(lit.) | | Boiling point | 427.9±28.0 °C(Predicted) | | density | 1.07±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | 1.85±0.10(Predicted) | | form | solid | | color | white to yellow | | Water Solubility | Insoluble | | InChI | 1S/C16H21BN2O2/c1-15(2)16(3,4)21-17(20-15)14-10-18-19(12-14)11-13-8-6-5-7-9-13/h5-10,12H,11H2,1-4H3 | | InChIKey | ZVPORPUUZXIPEF-UHFFFAOYSA-N | | SMILES | CC1(C)OB(OC1(C)C)c2cnn(Cc3ccccc3)c2 | | CAS DataBase Reference | 761446-45-1(CAS DataBase Reference) |
| | 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester Usage And Synthesis |
| Chemical Properties | off-white to light yellow crystals or | | Uses | 1-Benzylpyrazole-4-boronic acid pinacol ester can be used:
- As a model compound in the study of the stability of boronate esters in different alcohols using the LCMS technique.
- As a substrate in the study of palladium-catalyzed methylation of heteroaryl boronate esters using iodomethane.
- As a substrate in the preparation of bromodifluoromethylthiolated arenes, applicable in the radiosynthesis of [18F]ArylSCF3 compounds.
| | Synthesis | GENERAL STEPS: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (3.0 g, 15.5 mmol) was mixed with bromomethylbenzene (3.2 g, 18.7 mmol) in a solution of DMF (30 mL) containing K2CO3 (4.3 g, 31.2 mmol) and stirred at room temperature overnight. After completion of the reaction, the reaction mixture was diluted with EtOAc (50 mL) and H2O (50 mL), the organic layer was separated and washed with brine (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel column chromatography using PE/EtOAc (5:1) as eluent to afford the target compound 1-benzyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (3.5 g, 12.3 mmol) as a light yellow solid in 79% yield.1H NMR (400 MHz. CDCl3): δ 7.81 (s, 1H), 7.66 (s, 1H), 7.37-7.29 (m, 3H), 7.24-7.22 (m, 2H), 5.30 (s, 2H), 1.29 (s, 12H). lcms (M + H) + 285. | | References | [1] Patent: US2018/296543, 2018, A1. Location in patent: Paragraph 0573; 0574; 0600
[2] Patent: WO2015/95767, 2015, A1. Location in patent: Page/Page column 284; 285
[3] Patent: WO2016/124508, 2016, A1. Location in patent: Page/Page column 55
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1370 - 1387
[5] Patent: WO2014/60395, 2014, A1. Location in patent: Page/Page column 35 |
| | 1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester Preparation Products And Raw materials |
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