2-(DIMETHYLAMINE)PHENYLBORONIC ACID Chemical Properties

Melting point:

70 °C

Boiling point:

317.0±44.0 °C(Predicted)

Density 

1.12±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

8.86±0.58(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

2931900090

2-(DIMETHYLAMINE)PHENYLBORONIC ACID Usage And Synthesis

Uses

2-(Dimethylamino)phenylboronic acid

Synthesis

The general procedure for the synthesis of 2-(dimethylamino)benzeneboronic acid from trimethyl borate and 2-bromo-N,N-dimethylaniline is as follows: dissolve N,N-dimethyl-o-bromoaniline (4 g, 20 mmol) in anhydrous tetrahydrofuran (100 mL) at -78 °C, slowly add 2.5 M n-butyllithium solution (10 mL, 25 mmol) dropwise, and leave it at that temperature with continuous stirring for 2 hours. Subsequently, trimethyl borate (2.6 g, 25 mmol) was added to the reaction mixture and stirring was continued for 2 hours. Upon completion of the reaction, the mixture was slowly warmed to room temperature and the reaction was terminated by the addition of 0.1 N hydrochloric acid solution (200 mL). The reaction mixture was extracted with dichloromethane (150 mL x 3) and the organic phases were combined and washed with water (150 mL x 3). Finally, the organic phase was concentrated under reduced pressure to afford the target product 2-(dimethylamino)phenylboronic acid (3.0 g, 91% yield). The product was analyzed by LC-MS (ESI) and showed m/z = 166 [M + H]+.

References

[1] Patent: US2018/208604, 2018, A1. Location in patent: Paragraph 0465-0466

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