6-Quinolinecarbaldehyde Chemical Properties

Melting point:

74-75°C

Boiling point:

314.3±15.0 °C(Predicted)

Density 

1.223±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

4.13±0.10(Predicted)

color 

White to Yellow to Green

CAS DataBase Reference

4113-04-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36/38-36

Safety Statements 

26-37/39-36

HazardClass 

IRRITANT

HS Code 

29339900

6-Quinolinecarbaldehyde Usage And Synthesis

Chemical Properties

white to light yellow powde

Synthesis

General procedure for the synthesis of quinoline-6-carbaldehyde from 6-hydroxymethylquinoline: method adapted from Meyers et al. (Meyers, A. G.; Zhong, B.; Movassaghi, M.; Kung, D. W.; Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41, 1359-1362). Dess-Martin periodinane (2.57 g, 6.05 mmol) was added to a 0.28 M solution of 6-hydroxymethylquinoline (0.459 g, 2.88 mmol) in water-saturated dichloromethane (10 mL). The reaction mixture was stirred for 10 min and then dichloromethane (3 x 1 mL) was added in batches over 15 min. Subsequently, the reaction mixture was diluted with ether (10 mL) and 80% saturated aqueous sodium bicarbonate solution (10 mL) of sodium thiosulfate (7.87 g, 31.7 mmol) was added. The mixture was stirred rapidly for 45 minutes. The organic and aqueous layers were separated and the aqueous layer was extracted with ether (2 x 20 mL). The combined organic layers were washed sequentially with saturated aqueous sodium bicarbonate solution (30 mL), water (2 x 30 mL) and saturated sodium chloride solution (2 x 30 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (30-60% ethyl acetate/hexane) to give 0.383 g (85%) of quinoline-6-carbaldehyde (S4a) as a white solid with a melting point of 76.2-76.5 °C. 1H NMR (400 MHz, CDCl3): δ 7.53 (dd, 1H, J = 4.4, 8.4 Hz), 8.18-8.23 (m, 2H ), 8.33 (dd, 1H, J = 2.0, 8.4 Hz), 8.36 (s, 1H), 9.05 (dd, 1H, J = 2.0, 4.4 Hz), 10.20 (s, 1H).13C NMR (100 MHz, CDCl3): δ 122.4, 126.8, 127.8, 130.9, 133.8, 134.4 , 137.6, 151.0, 153.3, 191.6. HRMS-FAB (m/z): calculated value of 157.0528 for [MH]+ C10H7NO; measured value of 157.0521.

References

[1] Patent: WO2004/7491, 2004, A1. Location in patent: Page 56
[2] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6404 - 6410
[3] Patent: WO2009/75778, 2009, A2. Location in patent: Page/Page column 49; 50-51
[4] Patent: US2005/54670, 2005, A1. Location in patent: Page/Page column 27

6-Quinolinecarbaldehyde(4113-04-6)Related Product Information

• Quinclorac
• Quinoline Yellow
• Isoquinoline
• QUINOLINE SULPHATE
• Formaldehyde
• 6-Hydroxy-2(1H)-3,4-dihydroquinolinone
• 8-Hydroxyquinoline
• Ethoxyquin
• quinolinium hydrogen sulphate
• Quinhydrone
• 2-Quinolinecarboxaldehyde
• 6-Quinolinecarboxylic acid
• 3-Quinolinecarboxaldehyde
• Quinoline-5-carboxaldehyde
• quinoline-6-carbonitrile
• QUINOLINE-8-BORONIC ACID, PINACOL ESTER
• QUINOLINE-8-SULFONIC ACID
• Quinolin-3-yl-methanol