4-Di-p-tolylamino-benzaldehyde Chemical Properties

Melting point:

109 °C

Boiling point:

470.5±45.0 °C(Predicted)

Density 

1.138±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

almost transparency in hot Acetonitrile

form 

powder to crystal

pka

-4.76±0.50(Predicted)

color 

Light yellow to Amber to Dark green

InChI

InChI=1S/C21H19NO/c1-16-3-9-19(10-4-16)22(20-11-5-17(2)6-12-20)21-13-7-18(15-23)8-14-21/h3-15H,1-2H3

InChIKey

XCGLXUJEPIVZJM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

42906-19-4(CAS DataBase Reference)

EPA Substance Registry System

Benzaldehyde, 4-[bis(4-methylphenyl)amino]- (42906-19-4)

Safety Information

HS Code 

2922.39.4500

4-Di-p-tolylamino-benzaldehyde Usage And Synthesis

Chemical Properties

Light yellow - yellow-green powder

Synthesis

N,N-dimethylformamide (2.74 g, 37.5 mmol) was slowly added dropwise to a mixed system of 4,4'-dimethyltriphenylamine (2.27 g, 18.8 mmol) and phosphorus trichloride (5.65 g, 22.5 mmol) at 25 °C. The reaction mixture was continuously stirred and heated at 130 °C for 6 hours. Upon completion of the reaction, the system was cooled to room temperature and subsequently poured into 50 mL of cold water and extracted with chloroform (3 x 15 mL). The organic phases were combined, dried with anhydrous magnesium sulfate and filtered. Purification by recrystallization from dilute ethanol afforded the target product 4-di-p-tolylaminobenzaldehyde (R2-CHO). Yield: 1.75 g (31.5% yield). The melting point of the product was 96.3-97.5 °C. Electrospray ionization mass spectrometry (ESI-MS) showed the molecular ion peak ([M + H]+) m/z was 302.4.

References

[1] Chemical Communications, 2014, vol. 50, # 52, p. 6869 - 6871
[2] Dyes and Pigments, 2011, vol. 88, # 3, p. 333 - 343
[3] Tetrahedron, 2003, vol. 59, # 25, p. 4673 - 4685
[4] Dyes and Pigments, 2014, vol. 108, p. 32 - 40
[5] Journal of Chemical Crystallography, 2000, vol. 30, # 11, p. 749 - 753

4-Di-p-tolylamino-benzaldehyde(42906-19-4)Related Product Information

• 2-Aminobenzaldehyde
• 4-Aminobenzoic acid
• 4-Hydroxybenzaldehyde
• Phenylacetaldehyde
• p-Anisaldehyde
• Benzaldehyde
• Xylene
• 4-Dimethylaminobenzaldehyde
• o-Xylene
• p-Toluidine
• 4-Methylaniline hydrochloride
• 4-Aminobenzaldehyde
• sodium benzaldehyde-o-sulfonate
• Xylene formaldehyde resin
• TRIS(4-FORMYLPHENYL)AMINE
• 4-Bis(4-methylphenyl)aminobenzaldehyde-1,1-diphenyl-hydrazone
• 4,4'-Dimethyltriphenylamine
• Formaldehyde