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4-(N,N-Diphenylamino)benzaldehyde

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CAS:4181-05-9
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4-(N,N-Diphenylamino)benzaldehyde manufacturers

4-(N,N-Diphenylamino)benzaldehyde Basic information
Product Name:4-(N,N-Diphenylamino)benzaldehyde
Synonyms:JACS-4181-5-9;4-(diphenylamino)-benzaldehyd;4-(DIPHENYLAMINO)BENZALDEHYDE;4-FORMYLTRIPHENYLAMINE;4-(N,N-DIPHENYLAMINO)BENZALDEHYDE;P-N,N-DIPHENYLAMINO-BENZALDEHYDE;P-FORMYLTRIPHENYLAMINE;4-(N,N-DIPHENYLAMINO)BENZALDEHYDE (P-) 98+%
CAS:4181-05-9
MF:C19H15NO
MW:273.33
EINECS:628-054-6
Product Categories:Pyrroles ,Pyrimidines;Yellow crystalline powder;White Powder;Phenylamine Series;Triphenylamine series;Aromatic Aldehydes & Derivatives (substituted)
Mol File:4181-05-9.mol
4-(N,N-Diphenylamino)benzaldehyde Structure
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.
form Solid
pka-5.61±0.30(Predicted)
color Pale yellow
Sensitive Air Sensitive
BRN 2732795
InChIInChI=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
InChIKeyUESSERYYFWCTBU-UHFFFAOYSA-N
SMILESC(=O)C1=CC=C(N(C2=CC=CC=C2)C2=CC=CC=C2)C=C1
CAS DataBase Reference4181-05-9(CAS DataBase Reference)
EPA Substance Registry SystemBenzaldehyde, 4-(diphenylamino)- (4181-05-9)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
8
TSCA TSCA listed
HS Code 29223990
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
4-(N,N-Diphenylamino)benzaldehyde Usage And Synthesis
Chemical PropertiesPale yellow powder
UsesIt is used as pharmaceutical intermediate.
Synthesis
Triphenylamine

603-34-9

4-(N,N-Diphenylamino)benzaldehyde

4181-05-9

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