3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZALDEHYDE Chemical Properties

Melting point:

50-54°C

Boiling point:

345.1±25.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Light yellow

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

2931900090

3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZALDEHYDE Usage And Synthesis

Synthesis

To a 500 mL sealed tube was added m-bromobenzaldehyde (9.25 g, 50.0 mmol), potassium acetate (9.8 g, 100 mmol), bis(pinacolato)diborane (15.3 g, 60.3 mmol) and 1,4-dioxane (50 mL). The reaction system was degassed with nitrogen for 15 min. Subsequently, Pd(dppf)Cl2 (0.82 g, 1.0 mmol) was added and the reaction mixture was stirred at 90°C overnight. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filtrate was separated by extraction with water and ethyl acetate. The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography to afford 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (11.5 g, 99% yield) as a colorless liquid.LCMS (M + H)+: 233.2; 1H NMR (DMSO-d6, 300 MHz) δ: 10.06 (s, 1H), 8.21 (s, 1H), 8.01-8.04 (d, 1H), 7.96-7.99 (d, 1H), 7.61-7.66 (t, 1H), 1.33 (s, 12H).

References

[1] Patent: WO2014/202580, 2014, A1. Location in patent: Page/Page column 80; 81
[2] Patent: WO2014/202528, 2014, A1. Location in patent: Page/Page column 67
[3] Advanced Synthesis and Catalysis, 2016, vol. 358, # 6, p. 977 - 983
[4] Journal of Photochemistry and Photobiology A: Chemistry, 2018, vol. 364, p. 6 - 15
[5] Journal of the American Chemical Society, 2016, vol. 138, # 1, p. 84 - 87

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