| Identification | More | [Name]
6-Quinolinecarboxylic acid | [CAS]
10349-57-2 | [Synonyms]
6-QUINOLINECARBOXYLIC ACID
AKOS BBS-00005339
IFLAB-BB F0406-3604
QUINOLINE-6-CARBOXYLIC ACID
TIMTEC-BB SBB003821
Quinoline-6-CarboxylicAcid98%
CHINOLINE-6-CARBOXYLIC ACID
Quinoline-6-carboxylic acid 98%
6-Quinolinecarboxylic acid, 98% (titr.) | [EINECS(EC#)]
233-761-4 | [Molecular Formula]
C10H7NO2 | [MDL Number]
MFCD00047613 | [Molecular Weight]
173.17 | [MOL File]
10349-57-2.mol |
| Chemical Properties | Back Directory | [Appearance]
beige to brown crystalline powder | [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 | [form ]
Crystalline Powder | [pka]
3.05±0.30(Predicted) | [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]
10349-57-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29334900 |
| Hazard Information | Back Directory | [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 |
|
|