4-(N,N-Diphenylamino)benzaldehyde Chemical Properties

Melting point:

129-133 °C (lit.)

Boiling point:

436.8±28.0 °C(Predicted)

Density 

1.176±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

pka

-5.61±0.30(Predicted)

form 

Solid

color 

Pale yellow

Sensitive 

Air Sensitive

BRN 

2732795

InChI

InChI=1S/C19H15NO/c21-15-16-11-13-19(14-12-16)20(17-7-3-1-4-8-17)18-9-5-2-6-10-18/h1-15H

InChIKey

UESSERYYFWCTBU-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1

CAS DataBase Reference

4181-05-9(CAS DataBase Reference)

EPA Substance Registry System

Benzaldehyde, 4-(diphenylamino)- (4181-05-9)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

8

TSCA 

Yes

HS Code 

29223990

MSDS

• Language:English Provider:SigmaAldrich

4-(N,N-Diphenylamino)benzaldehyde Usage And Synthesis

Chemical Properties

Pale yellow powder

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

4-(N,N-Diphenylamino)benzaldehyde(4181-05-9)Related Product Information

• 3,4-Dichloroaniline
• Phenothiazine
• 2,4-Difluoroaniline
• 2,4-Dimethoxyaniline
• 3,4-Dimethylbenzaldehyde
• 2,4-Dichloroaniline
• Benzaldehyde
• Sodium diphenylamine-4-sulfonate
• Diphenylamine
• 4-Aminoveratrole
• 3,4-Difluoroaniline
• 2,4-Dimethylbenzaldehyde
• DIPHENYLAMINE-4-SULFONIC ACID BARIUM SALT
• 2,4-Dinitroaniline
• TRIS(4-FORMYLPHENYL)AMINE
• 4-Di-p-tolylamino-benzaldehyde
• Triphenylamine
• Formaldehyde