Chemical Properties
Pale yellow powder
Chemical Properties
4-(N,N-Diphenylamino)benzaldehyde is stable in acidic solutions but unstable in basic solutions and it emits fluorescence when irradiated with UV light.
Uses
4-(N,N-Diphenylamino)benzaldehyde (DPAB) excited by visible-light could be reductively quenched by a RAFT reagent 4-cynao-4-(phenylcarbonothioylthio)pentanoic acid. Besides, DPAB as a photoredox catalyst was also successfully used in synthesis of α,ω-dithiol and α,ω-divinyl telechelic polythioether oligomers through thiol-ene click polymerization of 1,4-benzenedimethane (BDMT) and diethylene glycol divinyl ether (DEGVE)
[1].
Uses
It is used as pharmaceutical intermediate.
Synthesis
Phosphoryl chloride (24 mL, 315 mmol) was slowly added dropwise to N,N-dimethylformamide (DMF, 30 mL) at 0 °C and the reaction mixture was stirred for 1 h keeping this temperature. Subsequently, triphenylamine (10 g, 40 mmol) was added and the reaction system was warmed to 100 °C with continuous stirring for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, slowly poured into ice water and the pH was adjusted with 5% aqueous sodium hydroxide to 7. The aqueous phase was extracted with ethyl acetate and the combined organic phases were dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by column chromatography using a mixed solvent of petroleum ether and dichloromethane (2:1, v/v/v) as eluent, and finally 4-diphenylaminobenzaldehyde was obtained as a white solid (5.76 g) in 52.74% yield.
References
[1] Inorganic Chemistry, 2017, vol. 56, # 5, p. 2409 - 2416
[2] Dyes and Pigments, 2014, vol. 100, # 1, p. 127 - 134
[3] Patent: US6603020, 2003, B1
[4] Patent: EP771809, 1997, A1
[5] Patent: EP1087006, 2001, A1
References
[1] Wang, Y., Liao, Q., Fan, Y., Chen, D., Ma, Y., Zhao, C., Yang, W. (2022). Surface engineering of Si wafers with tunable surface morphology and stiffness via visible light induced thiol-ene click polymerization with 4-(N,N-diphenylamino)benzaldehyde as an organocatalyst. Journal of Applied Polymer Science, 139 30.
https://doi.org/10.1002/app.52677
