TRANS-2-(4-METHYLPHENYL)VINYLBORONIC AC& Chemical Properties

Melting point:

169-175 °C(lit.)

Boiling point:

330.9±45.0 °C(Predicted)

Density 

1.100±0.06 g/cm3(Predicted)

storage temp. 

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

pka

9.70±0.43(Predicted)

form 

solid

Appearance

White to off-white Solid

Safety Information

WGK Germany 

3

HS Code 

2931900090

TRANS-2-(4-METHYLPHENYL)VINYLBORONIC AC& Usage And Synthesis

General Description

Contains varying amount of anhydride

Synthesis

General procedure for the synthesis of trans-2-(4-tolyl)vinylboronic acid from 1-ethynyl-4-methylbenzene and catecholborane: 1-ethynyl-4-methylbenzene (0.50 mL, 3.94 mmol, 1.00 equiv) and catecholborane (0.50 mL, 4.73 mmol, 1.20 equiv) were dissolved in tetrahydrofuran (THF, 1.5 mL) , and the mixture was refluxed for 18 hours. After completion of the reaction, the solvent was removed by evaporation and water (1 mL) was added. The resulting suspension was stirred vigorously for 4 h at room temperature. The solid was collected by filtration and recrystallized with water. Subsequent filtration afforded (E)-2-(4-tolyl)vinylboronic acid (309.4 mg, 1.90 mmol, 48% yield) and dried under vacuum. The product was characterized by 1H NMR (400 MHz, DMSO-d6) and 13C NMR (101 MHz, DMSO-d6) with the following data: 1H NMR (DMSO-d6) δ 7.73 (s, 2H), 7.36 (d, J = 7.9 Hz, 2H), 7.18 (d, J = 7.9 Hz, 2H), 6.05 (d, J = 18.3 Hz, 1H), 2.31 (s, 3H); 13C NMR (DMSO-d6) δ 146.2, 138.4, 135.4, 129.8 (2C), 127.0 (2C), 21.3.

References

[1] Patent: WO2016/198836, 2016, A1. Location in patent: Paragraph 00140
[2] Organic Letters, 2014, vol. 16, # 13, p. 3444 - 3447

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