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594823-67-3

594823-67-3 Structure

594823-67-3 Structure
IdentificationBack Directory
[Name]

3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene
[CAS]

594823-67-3
[Synonyms]

3-Bromophenylboronic acid, pinacol ester
2-(3-BroMophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene
1,3,2-Dioxaborolane, 2-(3-bromophenyl)-4,4,5,5-tetramethyl-
2-(3-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane10g
1-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
[Molecular Formula]

C12H16BBrO2
[MDL Number]

MFCD12545926
[MOL File]

594823-67-3.mol
[Molecular Weight]

282.969
Chemical PropertiesBack Directory
[Melting point ]

48 °C
[Boiling point ]

333.2±25.0 °C(Predicted)
[density ]

1.29±0.1 g/cm3(Predicted)
[storage temp. ]

Room temperature.
[solubility ]

soluble in Methanol
[form ]

powder to crystal
[color ]

White to Almost white
Questions And AnswerBack Directory
[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.
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H332-H312
[Precautionary statements ]

P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501-P261-P271-P304+P340-P312
[HS Code ]

2931900090
Spectrum DetailBack Directory
[Spectrum Detail]

3-Bromo-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-yl)benzene(594823-67-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

Pinacol

76-09-5

3-Bromophenylboronic acid

89598-96-9

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

594823-67-3

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
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