2-(BENZOFURAN-2-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE Chemical Properties

Boiling point:

340.0±15.0 °C(Predicted)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

solid

color 

Off-white to light yellow

InChI

InChI=1S/C14H17BO3/c1-13(2)14(3,4)18-15(17-13)12-9-10-7-5-6-8-11(10)16-12/h5-9H,1-4H3

InChIKey

GVWNFCUCNAWDNO-UHFFFAOYSA-N

SMILES

O1C2=CC=CC=C2C=C1B1OC(C)(C)C(C)(C)O1

Safety Information

HS Code 

2932990090

2-(BENZOFURAN-2-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE Usage And Synthesis

Synthesis

General procedure for the synthesis of benzofuran-2-boronic acid pinacol esters from 2,3-benzofuran and pinacolborane: According to the reaction scheme for the boronation of Example 9-aromatic five-membered heterocyclic rings (Fig. 2a), cobalt complex (0.01 mmol, selected from 1-4), 2-methylfuran (1 mmol), and pinacolborane (1 mmol) were added to a scintillation vial fitted with magnetic stirring bar. 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 stopper, followed by 1H and 13C NMR spectroscopy without further purification. Depending on the experimental requirements, the above reaction can also be carried out in 2 ml of tetrahydrofuran (THF). Figure 2a illustrates the percentage conversion of cobalt complexes 1-4, with the values in parentheses being the isolated yields. In addition, Figure 2b describes in detail the results of other boronation products achieved using cobalt complexes 2 and 3 under the same reaction conditions.

References

[1] Chemical Communications, 2003, # 23, p. 2924 - 2925
[2] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4133 - 4136
[3] Patent: WO2015/89119, 2015, A1. Location in patent: Page/Page column 34
[4] Chemical Communications, 2003, # 23, p. 2924 - 2925
[5] ACS Catalysis, 2018, vol. 8, # 6, p. 5017 - 5022

2-(BENZOFURAN-2-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(402503-13-3)Related Product Information

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