3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene Chemical Properties

Melting point:

48 °C

Boiling point:

333.2±25.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

Safety Information

HS Code 

2931900090

3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene Usage And Synthesis

Uses

Pinaryl 3-bromophenylboronic acid can be used to synthesize a green iridium(III) complex with high luminous efficiency. It contains special functional groups, namely fluorophenyl groups with electron transport properties, which are beneficial to the transport balance of charge carriers in the recombination region, thus enabling organic electroluminescent devices to have better performance.

Synthesis

The general procedure for the synthesis of 3-bromophenylboronic acid pinacol ester using 3-bromophenylboronic acid and pinacol as raw materials is as follows: 3-bromophenylboronic acid and pinacol were mixed in a suitable solvent under dry reaction conditions, a catalyst (e.g., sulfuric acid or p-toluenesulfonic acid) was added, and the reaction was carried out at room temperature with stirring. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the crude product obtained was purified by column chromatography to give 3-bromophenylboronic acid pinacol ester in 77% yield, and the product was an oil. Its 1H NMR (300 MHz, CDCl3) data were as follows: δ1.35 (s, 12H), 7.23 (t, 1H), 7.58 (dd, 1H), 7.70 (d, 1H), 7.93 (bs, 1H).

References

[1] Journal of Organic Chemistry, 2007, vol. 72, # 17, p. 6618 - 6620
[2] Chemical Communications, 2015, vol. 51, # 14, p. 2878 - 2881
[3] Patent: WO2003/105860, 2003, A1. Location in patent: Page 33
[4] Patent: WO2015/110999, 2015, A1. Location in patent: Page/Page column 63
[5] Organic Letters, 2010, vol. 12, # 23, p. 5474 - 5477

3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene(594823-67-3)Related Product Information

• 3-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER
• Bis(pinacolato)diboron
• (4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE
• Pinacol vinylboronate