tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate
1-Boc-pyrazole-4-boronic acid pinacol ester
CAS: 552846-17-0
Molecular Formula: C14H23BN2O4
tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate - Names and Identifiers
tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate - Physico-chemical Properties
| Molecular Formula | C14H23BN2O4 |
| Molar Mass | 294.15 |
| Density | 1.09±0.1 g/cm3(Predicted) |
| Melting Point | 82-86 °C (lit.) |
| Boling Point | 387.9±34.0 °C(Predicted) |
| Flash Point | 188.393°C |
| Water Solubility | insoluble |
| Solubility | soluble in Methanol |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | Crystalline Powder |
| Color | White to beige |
| pKa | -1.20±0.12(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.502 |
| MDL | MFCD05663873 |
tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| HS Code | 29339900 |
tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate - Reference Information
| Properties | 1-Boc-pyrazole -4-borate pinacol ester is white or off-white solid at room temperature and pressure. |
| Uses | 1-Boc-pyrazol-4-borate pinacol ester is a pyrazole derivative, mainly used as a synthetic intermediate for drug molecules and biologically active molecules. In the synthetic transformation, the boron unit on the pyrazole ring is a very practical functional group conversion precursor. The boron unit can be easily converted into a nitrogen atom, or it can be easily oxidized to a hydroxyl group, or through Suzuki coupling The reaction is connected to an aryl or alkyl group at the position of the boron unit. |
| synthesis method | chlorine (1,5-cyclooctadiene)(1,1 '-phenanthroline) iridium tetrahydrofuran adduct (5.8 mg, 0.01 mmol, 0.5 mol%) and pinacyl biborate were added to an open reaction bottle, the vial was sealed with a screw cap with a diaphragm, and the vial was replaced with nitrogen by three cycles of vacuum under vacuum. Prepare a stock solution of pinalborane (0.050 mL,44.1 mg,0.344 mmol) in tetrahydrofuran (50 mL,0.0067 M) in the second flask. The stock solution (1.4 ml, 1 equivalent of pinanol borane) was injected into a mixed system of chlorine (1,5 cyclooctadiene)(1,1 '-phenanthroline) iridium tetrahydrofuran adduct and pinacol borate, and the resulting reaction mixture was heated to 65 degrees for 1 hour until a dark red solution was formed. 0.336g of 1H-pyrazole -1-formate tert-butyl ester was directly added into dark red solution and allowed to react for several hours. The progress of the reaction was monitored by GC, GC-MS and TLC. When the reaction is completed, cool the vial, remove the solid precipitate by diatomite filtration, evaporate and spin dry the obtained filtrate under vacuum, dissolve the obtained residue with dichloromethane, and purify and separate the residue by column chromatography (0:100-1:1 ethyl acetate and n-hexane) to obtain the target product 1-Boc-pyrazole -4-borate pinacol ester. Fig. 1-Boc-pyrazole -4-borate pinacol ester synthesis route |
Last Update：2024-04-10 22:29:15
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