2-Methylfurane-5-boronic acid pinacol ester

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2-Methylfurane-5-boronic acid pinacol ester Basic information
Product Name:2-Methylfurane-5-boronic acid pinacol ester
Synonyms:2-Methylfurane-5-boronic acid pinacol ester;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-furanboronic acid pinacol ester;5-Methylfuran-2-boronic acid p;5-Methylfuran-2-boronic acid pinacol ester 95%;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;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)-
CAS:338998-93-9
MF:C11H17BO3
MW:208.06
EINECS:
Product Categories:
Mol File:338998-93-9.mol
2-Methylfurane-5-boronic acid pinacol ester Structure
2-Methylfurane-5-boronic acid pinacol ester Chemical Properties
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
InChI1S/C11H17BO3/c1-8-6-7-9(13-8)12-14-10(2,3)11(4,5)15-12/h6-7H,1-5H3
InChIKeyFNPZFZKLYGWKLH-UHFFFAOYSA-N
SMILESCc1ccc(o1)B2OC(C)(C)C(C)(C)O2
Safety Information
WGK Germany 3
HS Code 2932190090
Storage Class12 - Non Combustible Liquids
MSDS Information
2-Methylfurane-5-boronic acid pinacol ester Usage And Synthesis
Uses5-Methyl-2-furanboronic Acid Pinacol Ester is used as a reagent for the borylation of furans, pyrroles and other organic reactions.
Synthesis
2-Methylfuran

534-22-5

Pinacolborane

25015-63-8

2-Methylfurane-5-boronic acid pinacol ester

338998-93-9

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
2-Methylfurane-5-boronic acid pinacol ester Preparation Products And Raw materials
Raw materials2-Methylfuran-->1,3,2-Dioxaborolan-2-amine, N,N,4,4,5,5-hexamethyl--->Pinacolborane-->APD-I-->Cyclophosphamide
Preparation ProductsCPI-444
Tag:2-Methylfurane-5-boronic acid pinacol ester(338998-93-9) Related Product Information
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