2-BUTYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE Chemical Properties

Boiling point:

185-189

Density 

0.865

refractive index 

1.4182

Flash point:

58°C

storage temp. 

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

Appearance

Colorless to light yellow Liquid

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-24/25

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HS Code 

29319090

2-BUTYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE Usage And Synthesis

Chemical Properties

Clear colorless to brown liquid

Uses

n-Butylboronic acid pinacol ester can be used to prepare the fusaric acid and its analogs as possible inhibitors of quorum sensing in bacteria.

Synthesis

Under argon protection, 17.1 g (0.10 mol) of PinB (DMA) was added to a 500 mL reaction flask containing 100 mL of tetrahydrofuran. The temperature of the reaction system was lowered to 0~5°C and 44.3 mL of a 2.5 M solution of n-butyllithium (0.11 mol) was slowly added dropwise and stirred for 30 minutes keeping the temperature at 0~5°C. The reaction system was then warmed to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction was quenched by slow dropwise addition of 200 mL of 1 M KH2PO4 buffer and then extracted three times with 150 mL of ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the organic phase was concentrated. To the concentrate was added 40 g of n-hexane and filtered to give 12.9 g of white solid product in 70% yield and >97% GC purity. The 1H NMR, 11B NMR and IR spectra of the product were consistent with those of the standard.

References

[1] Patent: CN102093399, 2016, B. Location in patent: Paragraph 0027-0028

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