| Identification | Back Directory | [Name]
2-Methylfurane-5-boronic acid pinacol ester | [CAS]
338998-93-9 | [Synonyms]
5-Methylfuran-2-boronic acid p 5-Methyl-2-furanboronic acid pinacol ester 2-Methylfurane-5-boronic acid pinacol ester 5-Methylfuran-2-boronic acid pinacol ester 95% (5-Methylfuran-2-yl)boronic Acid Pinacol Ester 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan 2-(5-Methyl-2-furanyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(5-methyl-2-furanyl)- 5-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)furan, 2-(5-Methylfur-2-yl)-4,4,5 5-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)furan, 2-(5-Methylfur-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | [Molecular Formula]
C11H17BO3 | [MDL Number]
MFCD03094689 | [MOL File]
338998-93-9.mol | [Molecular Weight]
208.06 |
| Chemical Properties | Back Directory | [Melting point ]
217° | [Boiling point ]
277.8±28.0 °C(Predicted) | [density ]
1.023 g/mL at 25 °C | [refractive index ]
n20/D1.476 | [storage temp. ]
2-8°C | [form ]
clear liquid | [color ]
Light yellow to Yellow to Orange |
| Hazard Information | Back Directory | [Uses]
5-Methyl-2-furanboronic Acid Pinacol Ester is used as a reagent for the borylation of furans, pyrroles and other organic reactions. | [Synthesis]
The general procedure for the synthesis of 2-methylfuran-5-boronic acid pinacol ester from 2-methylfuran and pinacolborane is as follows: according to the reaction scheme for the boronation of Example 9-aromatic five-membered heterocyclic rings (Fig. 2a), to a scintillation vial fitted with a magnetic stirring bar were added a cobalt complex of 1-4,2-methylfuran (0.01 mmol), 2-methylfuran (1 mmol) and pinacolborane ( 1 mmol). The reaction process was monitored by analyzing an aliquot of the mixture by GC-FID. The reaction mixture was stirred at room temperature until the reaction was complete and subsequently quenched by exposure to air. The resulting solid was dissolved in CDCl3 and filtered through a Pasteur pipette fitted with a silicone plug, followed by 1H and 13C NMR spectroscopy without further purification. If the reaction conditions need to be adjusted, the above reaction can be carried out in 2 ml of tetrahydrofuran (THF). Figure 2(a) demonstrates the percentage conversion of cobalt complexes 1-4, and the values in parentheses are the isolated yields. In addition, Figure 2(b) describes in detail the other boronation products achieved using cobalt complexes 2 and 3 according to the aforementioned reaction parameters. | [References]
[1] Patent: WO2015/89119, 2015, A1. Location in patent: Page/Page column 34 [2] ACS Catalysis, 2018, vol. 8, # 6, p. 5017 - 5022 [3] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4133 - 4136 [4] Chemistry - An Asian Journal, 2010, vol. 5, # 7, p. 1657 - 1666 [5] Science, 2015, vol. 349, # 6247, p. 513 - 516 |
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