4-broMo-N,N-bis(4-Methoxyphenyl)aniline Chemical Properties

Melting point:

96-98℃

Boiling point:

494.6±40.0 °C(Predicted)

Density 

1.349±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

-2.37±0.50(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C20H18BrNO2/c1-23-19-11-7-17(8-12-19)22(16-5-3-15(21)4-6-16)18-9-13-20(24-2)14-10-18/h3-14H,1-2H3

InChIKey

XXCDCFFPMMCPEE-UHFFFAOYSA-N

SMILES

C1(N(C2=CC=C(Br)C=C2)C2=CC=C(OC)C=C2)=CC=C(OC)C=C1

Safety Information

HS Code 

2921.49.5000

4-broMo-N,N-bis(4-Methoxyphenyl)aniline Usage And Synthesis

Synthesis

4-Bromo-N,N-bis(4-methoxyphenyl)aniline was synthesized as follows: 1. 4,4'-Dimethoxytriphenylamine (9.0 g, 29.5 mmol) was dissolved in 100 mL of dimethylformamide (DMF) in a 250 mL round bottom flask. 2. N-bromosuccinimide (NBS, 5.25 g, 29.5 mmol) was dissolved in 30 mL of DMF and slowly added dropwise to the above reaction mixture. 3. The reaction mixture was stirred at room temperature and the reaction process was monitored by thin layer chromatography (TLC) for 23 hours. 4. Upon completion of the reaction, the reaction was quenched with 600 mL of water followed by extraction with dichloromethane (4 x 150 mL). 5. The organic layers were combined, washed with saturated sodium thiosulfate solution (4 x 150 mL) and dried over anhydrous sodium sulfate. 6. Concentrate under pressure to remove the solvent and obtain the crude product. 7. The crude product was purified by rapid chromatography on silica gel with a 5:1 hexane/ethyl acetate solvent mixture as eluent to afford the pure 4-bromo-N,N-bis(4-methoxyphenyl)aniline (12.1 g, 100% yield). 8. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 7.28 (d, J = 9.0 Hz, 2H), 7.05 (d, J = 9.0 Hz, 4H), 6.90 (d, J = 9.0 Hz, 4H), 6.73 (d, J = 9.0 Hz, 2H), 3.77 (s, 6H).

References

[1] Patent: WO2010/115854, 2010, A1. Location in patent: Page/Page column 28
[2] Patent: JP5670329, 2015, B2. Location in patent: Paragraph 0064
[3] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1997, # 7, p. 1405 - 1414
[4] Journal of Materials Chemistry A, 2018, vol. 6, # 17, p. 7950 - 7958
[5] Journal of the American Chemical Society, 2015, vol. 137, # 51, p. 16172 - 16178