(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol Chemical Properties

Melting point:

42-46 °C

Boiling point:

363.7±25.0 °C(Predicted)

Density 

1.07±0.1 g/cm3(Predicted)

Flash point:

110 °C

storage temp. 

Inert atmosphere,2-8°C

pka

14.34±0.10(Predicted)

form 

powder to lump

color 

White to Almost white

InChI

InChI=1S/C13H19BO3/c1-12(2)13(3,4)17-14(16-12)11-7-5-6-10(8-11)9-15/h5-8,15H,9H2,1-4H3

InChIKey

ZEWWJJQAFTXUIS-UHFFFAOYSA-N

SMILES

C1(CO)=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1

Safety Information

WGK Germany 

3

HS Code 

2931900090

(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol Usage And Synthesis

Uses

Pinaryl 3-hydroxymethylphenylboronic acid can be used as a pharmaceutical synthesis intermediate.

Synthesis

GENERAL METHOD: Methanol (12.50 mL) was added to a mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (1a, 375 mg, 2.50 mmol), pinacol (355 mg, 3.00 mmol) and anhydrous magnesium sulfate (625 mg, 5.00 mmol). The mixture was stirred at room temperature for 6 hours. Upon completion of the reaction, the crude reaction mixture was filtered and then sodium borohydride (47 mg, 1.25 mmol) was added to the filtrate. Subsequently, the reaction mixture was stirred for another 5 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated in vacuum to afford the target product 3-hydroxymethylphenylboronic acid pinacol ester (2a) as a white solid (melting point 75-77 °C) in 88% yield (513 mg).1H-NMR (CD3OD-d4) δ ppm: 7.71 (d, J=8.0 Hz, 2H), 7.35 (d, J=7.8 Hz. 2H), 4.62 (s, 2H), 1.34 (s, 12H); 13C-NMR (CD3OD-d4) δppm: 146.23, 135.93, 127.26, 85.19, 65.24, 25.34; 11B-NMR (CDCl3) δppm: 34.82.

References

[1] Molecules, 2013, vol. 18, # 10, p. 12346 - 12367

(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol(443776-76-9)Related Product Information

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