7-Quinolinecarboxylic acid Chemical Properties

Melting point:

249.5°C

Boiling point:

303.81°C (rough estimate)

Density 

1.2427 (rough estimate)

refractive index 

1.5200 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

2.68±0.30(Predicted)

color 

Off-white

InChI

InChI=1S/C10H7NO2/c12-10(13)8-4-3-7-2-1-5-11-9(7)6-8/h1-6H,(H,12,13)

InChIKey

WXXVQWSDMOAHHV-UHFFFAOYSA-N

SMILES

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

Safety Information

Safety Statements 

24/25

HS Code 

29334900

7-Quinolinecarboxylic acid Usage And Synthesis

Chemical Properties

Off-white powder

Uses

7-Quinolinecarboxylic acid is a reactant used in the chemical & genetic engineering of selective ion channel-ligand interactions.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 2721, 1946 DOI: 10.1021/ja01216a093

Synthesis

Step 1: An aqueous solution (50 mL) of lithium hydroxide monohydrate (5.42 g, 141 mmol, 3.0 equiv) was slowly added to a tetrahydrofuran solution (200 mL) of methyl 7-quinolinecarboxylate (8.8 g, 47 mmol). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the tetrahydrofuran was removed by distillation under reduced pressure. To the remaining aqueous phase, 1N aqueous hydrochloric acid solution (141 mL) was slowly added and the pH was adjusted to 7, at which time a white precipitate was produced. The precipitate was collected by filtration and washed sequentially with water and heptane. The resulting solid was dried in a vacuum oven at 50 °C to give 7-quinolinecarboxylic acid (8.4 g, 100% yield) as a white solid. Liquid chromatography analysis (detection wavelength 215 nm): retention time 0.66 min, purity 100%. Mass spectrum (electrospray positive ion mode): m/z 174 ([M+H]+). 1H NMR (400 MHz, d6-DMSO): δ 9.02 (1H, dd), 8.58 (1H, s), 8.48 (1H, d), 8.09 (2H, m), 7.66 (1H, dd).

References

[1] Patent: US2007/60567, 2007, A1. Location in patent: Page/Page column 27

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