4-Bromo-9H-carbazole Chemical Properties

Melting point:

104-105℃

Boiling point:

409.2±18.0 °C(Predicted)

Density 

1.617±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

16.04±0.30(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C12H8BrN/c13-9-5-3-7-11-12(9)8-4-1-2-6-10(8)14-11/h1-7,14H

InChIKey

CBJHFGQCHKNNJY-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2)C2=C1C=CC=C2Br

Safety Information

HS Code 

2933998090

4-Bromo-9H-carbazole Usage And Synthesis

Chemical Properties

White powder.

Uses

4-BroMo-9H-carbazole is a useful research chemical. 4-BroMo-9H-carbazole is a bromide-substitution of carbazole. The carbazole ring system is essentially planar (r.m.s. deviation of 0.024A for the non-H atoms). It is a photoelectric material intermediate and be used to synthesize OLED materials.    

Hazard

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Synthesis

Under nitrogen protection,Add 357.6g m-dibromobenzene (99%, 1.5mol) into a 500mL reaction flask,26.1g o-bromoaniline (99%, 0.15mol),0.084g palladium(II) acetate (99%, 0.375mmol),0.18g 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (99%, 0.375mmol),58.2g sodium tert-butoxide (99%, 0.6mol),After feeding,Warm up to 130°C,Stirring speed 600rpm,Incubate for 24hr,After the reaction,Vacuum distillation to recover unreacted m-dibromobenzene,Add water and ethyl acetate to extract the residue,The organic layer was desolvated to obtain the crude product which was crystallized in ethanol to obtain 34.3 g of 4-BroMo-9H-carbazole.The content is 99.6% and the yield is 92.5%.

References

[1] Organic Electronics: physics, materials, applications, 2013, vol. 14, # 1, p. 67 - 73
[2] Patent: WO2017/196081, 2017, A1. Location in patent: Paragraph 281; 282; 283; 284
[3] Patent: KR2016/6007, 2016, A. Location in patent: Paragraph 0439-0441
[4] Patent: KR2016/20159, 2016, A. Location in patent: Paragraph 0356-0359
[5] Patent: KR2015/133097, 2015, A. Location in patent: Paragraph 0282; 0283

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