| Identification | More | [Name]
4-Di-p-tolylamino-benzaldehyde | [CAS]
42906-19-4 | [Synonyms]
4,4'-Bis(4-methylphenyl)-aminobenzoaldehyde
4-[BIS(4-METHYLPHENYL)AMINO]BENZALDEHYDE
4-(DI-P-TOLYLAMINO)BENZALDEHYDE
4-FORMYL-4',4''-DIMETHYLTRIPHENYLAMINE
4-[bis(p-tolyl)amino]benzaldehyde
4-DI-P-TOLYAMINOBENALDEHYDE
4,4-Bis(4-methylphenyl)aminobenzaldehyde
4-(Di-p-Tlylamino)benzaldehyde
4-(N,N-Di-p-tolylamino)benzaldehyde
p-[N,N-Di-p-tolylamino]benzaldehyde | [EINECS(EC#)]
255-996-1 | [Molecular Formula]
C21H19NO | [MDL Number]
MFCD03093257 | [Molecular Weight]
301.38 | [MOL File]
42906-19-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
109 °C | [Boiling point ]
470.5±45.0 °C(Predicted) | [density ]
1.138±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,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 | [Detection Methods]
HPLC | [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]
42906-19-4(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow - yellow-green powder | [Uses]
Smart materials with tunable multiple-color emissions have been widely investigated in the fields of bioimaging, display, and information encryption. Multicolor emissive molecules with hydrazone bridged triphenylamines and pyridinium groups can be produced from 4-Di-p-tolylamino-benzaldehyde.
4-Di-p-tolylamino-benzaldehyde (0.603 g, 2 mmol) and 2-Hydrazinopyridine (0.442 g, 4 mmol) were stirred in 15 mL methanol at 90 °C for 24 h. After cooling to room temperature, the yellow crude product is extracted and filtered directly. Then yellow rod-like crystals were obtained by recrystallization in ethanol[1].
 | [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 |
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