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| | 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester Basic information |
| Product Name: | 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester | | Synonyms: | 1-METHYL-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-PYRAZOLE;1-METHYL-1H-PYRAZOLE-5-BORONIC ACID PINACOL ESTER;1-Methyl-1H-pyrazole-5-boronic acid pinacol;1-Methyl-1H-pyrazole-5-boronic acid pinacol ester
1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;2-(1-Methyl-1H-pyrazol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyrazole;1-Methyl-1H-pyrazole-3-boronic acid pinacol ester;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen (1-methyl-1H-pyrazol-5-yl)boronate | | CAS: | 847818-74-0 | | MF: | C10H17BN2O2 | | MW: | 208.07 | | EINECS: | | | Product Categories: | Pyrazole;Organoborons;Boronic ester | | Mol File: | 847818-74-0.mol |  |
| | 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester Chemical Properties |
| Melting point | 67-71 °C | | Boiling point | 308.3±15.0 °C(Predicted) | | density | 1.05±0.1 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | pka | 1.94±0.10(Predicted) | | form | crystal | | color | white | | Water Solubility | Slightly soluble in water. | | InChI | InChI=1S/C10H17BN2O2/c1-9(2)10(3,4)15-11(14-9)8-6-7-12-13(8)5/h6-7H,1-5H3 | | InChIKey | HLXOVAMYQUFLPE-UHFFFAOYSA-N | | SMILES | N1(C)C(B2OC(C)(C)C(C)(C)O2)=CC=N1 | | CAS DataBase Reference | 847818-74-0(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 26 | | WGK Germany | 3 | | TSCA | No | | HazardClass | IRRITANT | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester Usage And Synthesis |
| Chemical Properties | White to light brown solid | | Uses | 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester is used as a pharmaceutical intermediate, agrochemical intermediate. | | Synthesis | To a solution of 1-methylpyrazole (4.1 g, 50 mmol) in tetrahydrofuran (THF, 100 mL) was slowly added n-butyllithium (n-BuLi, 2.2 M solution in THF, 55 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour and then cooled to -78 °C. Subsequently, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (12.3 mL, 60 mmol) was added to the reaction system. The reaction was carried out at -78 °C for 15 min and then gradually warmed up to 0 °C, taking 1 hour. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride (NH4Cl) solution and extracted with dichloromethane (DCM). The organic phases were combined, washed with distilled water (2 × 100 mL), dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to afford the brown solid product 1-methyl-1H-pyrazole-5-boronic acid pinacol ester (8.0 g, 77% yield), which could be used for the subsequent reaction without further purification. The product was detected by liquid chromatography-mass spectrometry (LCMS, ES), showing m/z 127 (M+H)+ [RB(OH)2]; nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3, 400 MHz) showed δ 7.57 (s, 1H), 6.75 (s, 1H), 4.16 (s, 3H) and 1.41 (s, 12H). | | References | [1] Patent: WO2009/158372, 2009, A1. Location in patent: Page/Page column 30; 31
[2] Patent: WO2009/158374, 2009, A2. Location in patent: Page/Page column 30
[3] Patent: WO2008/98105, 2008, A1. Location in patent: Page/Page column 36
[4] Patent: US2010/216843, 2010, A1. Location in patent: Page/Page column 20-21
[5] Patent: WO2008/121786, 2008, A1. Location in patent: Page/Page column 42-43 |
| | 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester Preparation Products And Raw materials |
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