3-bromo-9-phenyl-9H-carbazole Chemical Properties

Melting point:

98 ºC

Boiling point:

461.7±27.0 °C(Predicted)

Density 

1.39

storage temp. 

Sealed in dry,Room Temperature

form 

Solid

color 

White to Almost white

Water Solubility 

Slightly soluble in water.

λmax

352nm(CH3CN)(lit.)

InChI

InChI=1S/C18H12BrN/c19-13-10-11-18-16(12-13)15-8-4-5-9-17(15)20(18)14-6-2-1-3-7-14/h1-12H

InChIKey

KUBSCXXKQGDPPD-UHFFFAOYSA-N

SMILES

N1(C2=CC=CC=C2)C2=C(C=CC=C2)C2=C1C=CC(Br)=C2

CAS DataBase Reference

1153-85-1(CAS DataBase Reference)

Safety Information

HS Code 

2933998090

3-bromo-9-phenyl-9H-carbazole Usage And Synthesis

Description

3-Bromo-9-phenylcarbazole is a chemical compound used as an intermediate in synthesizing organic compounds. It has applications in material science, such as in developing organic semiconductors and optoelectronic devices. It is used in the manufacturing of OLED materials. Also used as an intermediate for pharmaceuticals. This product should be handled with care due to its potential health hazards, including eye and skin irritation. Proper safety equipment, such as gloves and goggles, should be worn when handling this compound. Storage guidelines include keeping it in a cool, dry place away from sources of heat or ignition.

Chemical Properties

off-white powder

Uses

3-bromo-9-phenyl-9H-carbazole is a heterocyclic compound with a bromine functional group that can be used as an organic synthesis intermediate and optoelectronic material. Using 9-phenylcarbazole as the core, it can be used to synthesize starburst carbazoles and their derivatives via a Suzuki cross-coupling reaction. Fluorescence spectroscopy reveals that these compounds exhibit excellent blue fluorescence with a maximum wavelength between 410 and 430 nm.

Synthesis

The general procedure for the synthesis of 3-bromo-N-phenylcarbazole using 3-bromocarbazole and iodobenzene as starting materials was as follows: in a dry reaction flask, 3-bromo-9H-carbazole, iodobenzene, 0.03 equiv. of tris(dibenzylideneacetone)di-palladium(0) (Pd2(dba)3), 0.06 equiv. of tributylphosphine, and toluene (0.1 M) were added in sequence. The reaction mixture was stirred at room temperature for about 12 hours. Upon completion of the reaction, the mixture was cooled to ambient temperature, extracted with dichloromethane and the organic phase was washed with distilled water. The organic phase was collected and dried over anhydrous magnesium sulfate (MgSO4) and subsequently concentrated under reduced pressure. The residue was purified by column chromatography to afford the target product 3-bromo-9-phenyl-9H-carbazole in 87.22% yield. The exact mass of the compound was measured as 321 by high resolution mass spectrometry (HRMS) analysis and the molecular formula was confirmed as C18H12BrN.

References

[1] Patent: US2017/162796, 2017, A1. Location in patent: Paragraph 0126; 0127
[2] Patent: KR2015/58973, 2015, A. Location in patent: Paragraph 0106; 0107; 0108
[3] Patent: KR2016/51654, 2016, A. Location in patent: Paragraph 0244-0246
[4] Patent: KR2015/102733, 2015, A. Location in patent: Paragraph 0151-0155
[5] Patent: KR2015/112880, 2015, A. Location in patent: Paragraph 0119; 0120; 0121; 0122; 0123

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