5-PHENYL-2-THIENYLBORONIC ACID Chemical Properties

Melting point:

140 °C

Boiling point:

412.9±47.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

8.49±0.53(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2934999090

5-PHENYL-2-THIENYLBORONIC ACID Usage And Synthesis

Synthesis

Under nitrogen protection, 2-bromo-5-phenylthiophene (compound 111, 2.50 g, 10.4 mmol) was dissolved in anhydrous THF (50 mL) and cooled to -78 °C. Slowly n-butyllithium (n-BuLi, 8.4 mL of a 2.5 M hexane solution) was added dropwise. The reaction mixture was stirred at -78 °C for 1 h. Trimethyl borate (2.40 mL, 20.9 mmol) was slowly added. Stirring was continued at -78 °C for 30 min, followed by removal of the cooling bath to allow the reaction mixture to gradually warm to room temperature and stirring for 3 h at 37 °C. Upon completion of the reaction, the reaction was quenched with 1N HCl (100 mL) and subsequently extracted with ethyl acetate. The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was slurried with petroleum ether, filtered and dried to afford (5-phenylthiophen-2-yl)boronic acid (Compound 112, 1.04 g, 48.8% yield).

References

[1] Patent: US7485733, 2009, B2. Location in patent: Page/Page column 77
[2] Chemistry - A European Journal, 2002, vol. 8, # 10, p. 2384 - 2396
[3] Patent: US2008/108832, 2008, A1. Location in patent: Page/Page column 51
[4] Patent: EP2177516, 2010, A1. Location in patent: Page/Page column 46-47

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