N-(4-Bromophenyl)-[1,1'-biphenyl]-4-amine Chemical Properties

Melting point:

130.0 to 134.0 °C

Boiling point:

446.7±38.0 °C(Predicted)

Density 

1.368±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

pka

0.06±0.40(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C18H14BrN/c19-16-8-12-18(13-9-16)20-17-10-6-15(7-11-17)14-4-2-1-3-5-14/h1-13,20H

InChIKey

RDSXVQDXXSPFHG-UHFFFAOYSA-N

SMILES

C1(C2=CC=CC=C2)=CC=C(NC2=CC=C(Br)C=C2)C=C1

Safety Information

HS Code 

2921.49.5000

N-(4-Bromophenyl)-[1,1'-biphenyl]-4-amine Usage And Synthesis

Uses

N-(4-Bromophenyl)-[1,1-biphenyl]-4-amine is a useful reagent for preparing carbazole and dibenzofuran-linked tertiary arylamine compounds, which may improve electroluminescent properties.

Synthesis

The general procedure for the synthesis of N-(4-bromophenyl)-4-benzidine from N-phenyl-4-benzidine was as follows: N-phenyl-4-benzidine (35.0 g) was dissolved in DMF (700 ml) under the protection of nitrogen and cooled in an ice bath. Subsequently, N-bromosuccinimide (8.5 g) was slowly added. After the temperature of the reaction system was brought to room temperature, the remaining N-bromosuccinimide (total 17.0 g) was added in two portions. The reaction mixture was stirred at room temperature for 25.5 h. The reaction solution was slowly dripped into water (3,500 ml) to precipitate a solid, which was collected by filtration. The resulting solid was dissolved in toluene (2,500 ml) and dried by adding magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated. To the concentrate was added hexane (500 ml) for dispersion and washing, followed by drying under reduced pressure overnight to give N-(4-bromophenyl)-4-benzidine as a slightly red solid (44.1 g, 95.4% yield).

References

[1] Patent: EP2530069, 2012, A1. Location in patent: Page/Page column 34-35
[2] Patent: WO2009/72587, 2009, A1. Location in patent: Page/Page column 261-262
[3] Patent: EP2772483, 2014, A1. Location in patent: Paragraph 0159; 0160; 0161; 0162

N-(4-Bromophenyl)-[1,1'-biphenyl]-4-amine(1160294-93-8)Related Product Information

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