3-Bromodibenzo[b,d]furan Chemical Properties

Melting point:

232-233℃

Boiling point:

343.8±15.0 °C(Predicted)

Density 

1.4587 (rough estimate)

refractive index 

1.5290 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C12H7BrO/c13-8-5-6-10-9-3-1-2-4-11(9)14-12(10)7-8/h1-7H

InChIKey

AZFABGHLDGJASW-UHFFFAOYSA-N

SMILES

O1C2=CC=CC=C2C2=CC=C(Br)C=C12

CAS DataBase Reference

26608-06-0

Safety Information

HS Code 

2932990090

3-Bromodibenzo[b,d]furan Usage And Synthesis

Description

3-Bromodibenzo[b,d]furan can be used as a component of organic light emitting diode (OLED) materials. It is used as an electronic component and in electronic devices using organic compounds.

Chemical Properties

3-Bromodibenzofuran is a white crystal-Powder at 20°C. 3-Bromodibenzofuran can be used to synthesize a phosphorescent iridium complex containing a 3-phenylpyridazine structure.

Uses

3-Bromodibenzo[b,d]furan is a useful research chemical.

Synthesis

The general procedure for the synthesis of 3-bromodibenzo[b,d]furan from 3-aminodibenzofuran was as follows: in a 500 mL four-necked round-bottomed flask equipped with a stirrer, a thermometer, and a 200 mL dropping funnel, 19.0 g (102.6 mmol) of 3-amino-dibenzofuran, 190 mL of water, and 57 mL of 48% hydrobromic acid were added, and the mixture was stirred overnight. Subsequently, the reaction mixture was cooled to -10°C in an ice-water bath and 8.1 g (117.4 mmol) of sodium nitrite solution dissolved in 150 mL of water was added slowly and dropwise while keeping the temperature from rising. The reaction solution was stirred below 5 °C for 1 h to prepare to obtain the diazonium salt solution. Next, in a 1 L four-necked round-bottomed flask equipped with a stirrer, condenser, thermometer, and 500 mL dropping funnel, 16.2 g (116.9 mmol) of cuprous bromide, 38 mL of 48% hydrobromic acid, and 90 mL of water were added, and the mixture was cooled to 0°C and stirred. The previously prepared diazonium salt solution was slowly added dropwise at no more than 5 °C and stirring was continued at the same temperature for 30 min. Subsequently, the reaction temperature was raised to 40°C and stirred at that temperature for 18 hours. Upon completion of the reaction, 200 mL of water was added to the reaction solution, cooled to room temperature and extracted twice with 200 mL of dichloromethane (DCM). The organic layers were combined, washed sequentially with 100 mL of 5% aqueous sodium sulfite and 100 mL of saturated brine, and dried with magnesium sulfate. After filtration to remove the desiccant, the solvent was removed by distillation under reduced pressure. Finally, the crude product was purified by silica gel column chromatography using n-heptane as the unfolding agent to afford 17.2 g (yield: 68.0%) of the target compound 3-bromodibenzo[b,d]furan.

References

[1] Patent: JP2018/90561, 2018, A. Location in patent: Paragraph 0077
[2] Patent: CN108341795, 2018, A. Location in patent: Paragraph 0139; 0144; 0145
[3] Journal of the Chemical Society, 1935, p. 1131,1133
[4] Patent: EP1859798, 2015, B1. Location in patent: Paragraph 0141
[5] Patent: CN105481903, 2016, A. Location in patent: Paragraph 0061; 0062; 0063

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