4-Quinolinecarboxaldehyde Chemical Properties

Melting point:

45-52 °C (lit.)

Boiling point:

131-133°C 5mm

Density 

1.1599 (rough estimate)

refractive index 

1.5000 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

2.95±0.13(Predicted)

form 

Crystalline Powder, Chunks, or Solid

color 

Off-white to yellow-brown

Water Solubility 

Slightly soluble in water.

Sensitive 

Air Sensitive

BRN 

113072

InChI

InChI=1S/C10H7NO/c12-7-8-5-6-11-10-4-2-1-3-9(8)10/h1-7H

InChIKey

MGCGJBXTNWUHQE-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2)C(C=O)=CC=1

CAS DataBase Reference

4363-93-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-36/37/38

Safety Statements 

24/25-36-26-36/37/39

WGK Germany 

3

F 

10

HazardClass 

IRRITANT

HS Code 

29334900

MSDS

• Language:English Provider:4-Quinolinecarbaldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Quinolinecarboxaldehyde Usage And Synthesis

Chemical Properties

yellow to yellow-brown crystalline powder

Occurrence

The common presence of 4-quinolinecarboxaldehyde in honey from Galicia (northwest of Spain). As opposed to other quinoline carboxylic acid derivatives, the 4- quinolinecarboxaldehyde species has not been correlated with the anti-diabetic properties of honey; nevertheless, it appears to be active against intestinal bacteria.

Uses

4-Quinolinecarboxaldehyde was used in the synthesis of lepidylamines. It also shows antimicrobial activity toward human intestinal bacteria such as Clostridium perfringens.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 841, 1970 DOI: 10.1021/jo00828a074

Synthesis

The general procedure for the synthesis of 4-quinolinecarboxaldehyde from 4-methylquinoline was as follows: 5.0 g (35 mmol) of 4-methylquinoline and 5.0 g (45 mmol) of selenium dioxide were dissolved in toluene under argon protection and heated to reflux for 24 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane, washed sequentially with saturated saline and dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the reaction was purified by silica gel column chromatography using a solvent mixture of hexane and ethyl acetate (4:1, v/v) as eluent to give 4.0 g (73% yield) of the target product 4-quinolinecarboxaldehyde as a solid. Nuclear magnetic resonance hydrogen spectroscopy (1H NMR) data: δ 10.54 (s, 1H), 9.22 (d, J = 4.3 Hz, 1H), 9.04 (d, J = 8.6 Hz, 1H), 8.24 (d, J = 8.2 Hz, 1H), 7.84 (t, J = 7.6 Hz, 1H), 7.81 (d, J = 4.3 Hz, 1H), 7.76 (t , J = 8.0 Hz, 1H). Nuclear magnetic resonance carbon (13C NMR) data: δ 193.1, 150.7, 149.5, 137.0, 130.4, 130.3, 129.6, 126.0, 124.7, 124.1. mass spectrometry (electrospray ionization) data: m/z 158.0 (100%) ([M + H]+), 130.2.

References

[1] Tamara Rodríguez-Cabo. “Time-of-flight accurate mass spectrometry identification of quinoline alkaloids in honey.” Analytical and Bioanalytical Chemistry 407 20 (2015): 6159–6170.

4-Quinolinecarboxaldehyde(4363-93-3)Related Product Information

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