4-(4-Pyridinyl)benzaldehyde Chemical Properties

Melting point:

85-89 °C (lit.)

Boiling point:

336.7±25.0 °C(Predicted)

Density 

1.147±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

4.98±0.10(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C12H9NO/c14-9-10-1-3-11(4-2-10)12-5-7-13-8-6-12/h1-9H

InChIKey

MBJXDIYHLGBQOT-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(C2C=CN=CC=2)C=C1

CAS DataBase Reference

99163-12-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37/39-22

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

4-(4-Pyridinyl)benzaldehyde Usage And Synthesis

Chemical Properties

White solid

Synthesis

Pyridine-4-boronic acid (498.3 mg, 4.05 mmol) and p-bromobenzaldehyde (500 mg, 2.70 mmol) were added to bis(triphenylporphyrinophosphate) palladium dichloride Pd(PPh3)2Cl2 (94.65 mg, 0.14 mmol) as a catalyst and dissolved in 20 mL of a solvent mixture of tetrahydrofuran and toluene (Vtoluene: VTHF = 1:1) in it. The reaction mixture was heated to 90°C under nitrogen protection for reflux reaction and the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction solution was concentrated to remove the organic solvent and subsequently extracted with ethyl acetate. The organic layer was washed sequentially with water three times, saturated sodium chloride solution once, and then dried with anhydrous sodium sulfate. The dried organic phase was evaporated under reduced pressure to remove the solvent to obtain the crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate (20:1) as eluent to finally obtain 4-(pyridin-4-yl)benzaldehyde (white solid, 288.7 mg, 68.4% yield).

References

[1] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6622 - 6630
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 18, p. 8402 - 8416
[3] Crystal Growth and Design, 2018, vol. 18, # 11, p. 6936 - 6945
[4] Patent: CN105418515, 2016, A. Location in patent: Paragraph 0087; 0088; 0089
[5] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2761 - 2766

4-(4-Pyridinyl)benzaldehyde(99163-12-9)Related Product Information

• 4-Hydroxybenzaldehyde
• Pyridine
• 4-Pyridinecarboxaldehyde
• Benzaldehyde
• 4-Dimethylaminobenzaldehyde
• 2-Nitrobenzaldehyde
• 4-Pyrid-4-ylbenzoic acid
• rosoxacin
• 2-(4-PYRIDINYL)BENZALDEHYDE
• 3-(2-PYRIDINYL)BENZALDEHYDE
• 3-(3-PYRIDINYL)BENZALDEHYDE
• 4-(3-PYRIDINYL)BENZALDEHYDE
• 2-(3-PYRIDINYL)BENZALDEHYDE
• 4-(2-PYRIDINYL)BENZALDEHYDE
• 3-(4-PYRIDINYL)BENZALDEHYDE
• 4-(4-PYRIDYL)BENZOIC ACID, SODIUM SALT
• 4-(2,2':6',2''-TERPYRIDIN-4'-YL)BENZALDEHYDE
• METHYL 4-(4-PYRIDINYL)BENZOATE