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| | 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester Basic information |
| Product Name: | 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester | | Synonyms: | 2H-Pyran, 3,6-dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2h-pyran, 95%;3,6-Dihydro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2H-pyran;3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester;3,6-Dihydro-2H-pyran-4-bo...;3,6-Dihydro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;3,6-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyran, 2-(3,6-Dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester 97% | | CAS: | 287944-16-5 | | MF: | C11H19BO3 | | MW: | 210.08 | | EINECS: | | | Product Categories: | Boronate Esters;Boronic Acids and Derivatives;Organoborons;Chemical Synthesis;Heteroaryl Boronate Esters;Organometallic Reagents;Organic boronic acid | | Mol File: | 287944-16-5.mol |  |
| | 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester Chemical Properties |
| Melting point | 63-67℃ | | Boiling point | 238.6±50.0 °C(Predicted) | | density | 1.01±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | form | Solid | | color | White to off-white | | Water Solubility | Slightly soluble in water. | | Sensitive | Moisture Sensitive | | InChI | InChI=1S/C11H19BO3/c1-10(2)11(3,4)15-12(14-10)9-5-7-13-8-6-9/h5H,6-8H2,1-4H3 | | InChIKey | DOSGEBYQRMBTGS-UHFFFAOYSA-N | | SMILES | C1OCC=C(B2OC(C)(C)C(C)(C)O2)C1 |
| Hazard Codes | Xn | | Risk Statements | 22 | | Safety Statements | 20-35 | | WGK Germany | 3 | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral |
| | 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester Usage And Synthesis |
| Uses | It plays an important role as intermediate for organic synthesis agrochemical, pharmaceutical and dyestuff field. | | Uses | 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester can be used:
- To prepare 1,2-dihydro-2-oxopyridine based endocannabinoid system (ECS) modulators.
- As an intermediate in the synthesis of embryonic ectoderm development (EED) inhibitors.
- To prepare pyrrolotriazine based IRAK4 inhibitors.
| | Synthesis | To a 250 mL round-bottomed flask, a solution of 3,6-dihydro-2H-pyran-4-trifluoromethanesulfonate (2.7 g, 11.6 mmol), PdCl2(dppf) (440 mg, 0.6 mmol), and potassium acetate (3 g, 36 mmol) was added to a solution of dioxane (20 mL), which was subsequently displaced three times with argon to remove air. The reaction mixture was stirred at 80 °C overnight. Upon completion of the reaction, it was cooled to room temperature and filtered through a short column containing diatomaceous earth to remove solid impurities. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (eluent: 10% dichloromethane solution of hexane) to give the final white solid product 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester (2 g, 81% yield). | | References | [1] Patent: WO2008/153858, 2008, A1. Location in patent: Page/Page column 307
[2] Patent: US2012/316147, 2012, A1. Location in patent: Page/Page column 32
[3] Patent: WO2012/168350, 2012, A1. Location in patent: Page/Page column 76; 77
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 7, p. 666 - 670
[5] Patent: US2008/318935, 2008, A1. Location in patent: Page/Page column 65 |
| | 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester Preparation Products And Raw materials |
| Raw materials | 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[1-methylene-3-(2-propen-1-yloxy)propyl]--->Bis(pinacolato)diboron-->Pinacol-->4-BROMO-3,6-DIHYDRO-2H-PYRAN-->Trimethyl borate-->3,6-DIHYDRO-2H-PYRAN-4-YL TRIFLUORO-METHANESULFONATE-->Potassium Acetate-->1,4-Dioxane | | Preparation Products | 2-FLUORO-3-(TETRAHYDRO-2H-PYRAN-4-YL)-PYRIDINE-->4-(3-bromophenyl)-3,6-dihydro-2H-Pyran |
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