5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde Chemical Properties

Melting point:

66.0 to 70.0 °C

Boiling point:

359.1±27.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

form 

solid

color 

light brown

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37

TSCA 

No

HS Code 

2934999090

5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde Usage And Synthesis

Synthesis

PdCl2 (dppf) (756 mg, 0.88 mmol) and KOAc (2.587 g, 26.4 mmol) were added to degassed 1,4-dioxane (60 mL) under nitrogen protection using 5-bromothiophene-2-carboxaldehyde (1.68 g, 8.8 mmol) and pinacol ester of bis(boronic acid) (3.4 g, 13.2 mmol). The reaction mixture was stirred at 80 °C for 6 hours. Upon completion of the reaction, the reaction was quenched by the addition of water and extracted with dichloromethane. The organic phase was dried with anhydrous Na2SO4 and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/dichloromethane=1/3) to afford the target compound 5-formyl-2-thiopheneboronic acid pinacol ester (1.86 g, 88.9% yield) as a yellow solid. The melting point of the product was 73 °C. Mass spectra (EI) showed the molecular ion peak m/z=238 (M+).1H NMR (CDCl3, 400 MHz) δ/ppm: 9.92 (s, 1H), 7.73 (d, 1H), 7.43 (d, 1H), 1.34 (s, 12H).

References

[1] Tetrahedron, 2012, vol. 68, # 44, p. 9113 - 9118

5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde(1040281-83-1)Related Product Information

• POTASSIUM 5-FORMYLFURAN-2-YLTRIFLUOROBORATE
• Potassium 5-formylthiophene-2-trifluoroborate
• 5-Formylfuran-2-boronic acid, neopentyl glycol ester
• 5-Formyl-2-thiopheneboronic acid
• 2-Formylfuran-5-boronic acid
• 5-Formylfuran-2-boronic acid, pinacol ester