6-Quinolinecarboxylic acid Chemical Properties

Melting point:

293-294 °C

Boiling point:

303.81°C (rough estimate)

Density 

1.2427 (rough estimate)

refractive index 

1.5200 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Practically insoluble in water

pka

3.05±0.30(Predicted)

form 

Crystalline Powder

color 

Beige to brown

InChI

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

InChIKey

VXGYRCVTBHVXMZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

10349-57-2(CAS DataBase Reference)

EPA Substance Registry System

6-Quinolinecarboxylic acid (10349-57-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29334900

MSDS

• Language:English Provider:6-Quinolinecarboxylic acid
• Language:English Provider:ACROS
• Language:English Provider:ALFA

6-Quinolinecarboxylic acid Usage And Synthesis

Chemical Properties

beige to brown crystalline powder

Uses

6-Quinolinecarboxylic acid is a vital compound and can be used to synthesise 6-Quinolinecarboxaldehyde, 6-(Aminomethyl)quinoline, and Quinolin-6-ylmethanol, etc.

Synthesis

6-Methylquinoline (100.0 mg, 0.70 mmol) was dissolved in a mixed solution of H2O (1.0 mL) and H2SO4 (0.25 mL) at 0 °C and chromium trioxide (272.0 mg, 2.72 mmol) was added in batches. The reaction mixture was refluxed for 24 hours. After completion of the reaction, it was cooled to room temperature and the precipitated crystalline bisulfate precipitate was removed by filtration. The filtrate was dissolved in 10% aqueous sodium hydroxide solution, washed with hexane and the pH was adjusted to acidic with acetic acid to precipitate 6-quinolinecarboxylic acid. The precipitate was collected to give 85.0 mg of 6-quinolinecarboxylic acid in 70% yield. The product could be used in subsequent steps without further purification. The product was characterized as follows: 1H NMR (300 MHz, DMSO-d6) δ 7.61 (dd, 1H, J1 = 8.3 Hz, J2 = 4.2 Hz), 8.08 (d, 1H, J = 8.8 Hz), 8.20 (dd, 1H, J1 = 8.8 Hz, J2 = 1.7 Hz), 8.56 (d, 1H, J = 8.2 Hz), 8.67 (m, 1H, J = 8.2 Hz), 8.67 (m, 1H, J = 8.2 Hz), 8.56 (d, 1H, J = 8.2 Hz), 8.56 (m, 1H, J = 8.2 Hz) 8.67 (m, 1H), 9.00 (dd, 1H, J1 = 4.1 Hz, J2 = 1.5 Hz), 13.20 (br s, 1H); 13C NMR (300 MHz, DMSO-d6) δ 122.9, 127.9, 129.2, 129.5, 130.0, 131.7, 138.2, 150.0, 153.4, 167.4, 167.0, 153.4, 167.4, 167.4, 167.4, 167.4, 167.4, 167.4 153.4, 167.7; ESI-MS m/z 196 [M + Na]+, 174 [M + H]+. Molecular formula: C10H7NO2.

References

[1] Chemical Communications, 2002, # 2, p. 180 - 181
[2] Patent: WO2008/43839, 2008, A1. Location in patent: Page/Page column 10; 11
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 22, p. 9578 - 9597
[4] Heterocycles, 2011, vol. 83, # 7, p. 1649 - 1658
[5] Monatshefte fuer Chemie, 1891, vol. 12, p. 309

6-Quinolinecarboxylic acid(10349-57-2)Related Product Information

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