| Identification | More | [Name]
Quinoline-5-carboxaldehyde | [CAS]
22934-41-4 | [Synonyms]
5-QUINOLINECARBOXALDEHYDE
AKOS BBS-00005336
CHEMBRDG-BB 4300479
QUINOLINE-5-CARBALDEHYDE
QUINOLINE-5-CARBOXALDEHYDE
RARECHEM AK ML 0025
QUINOLINE-5-CARBOXALDEHYDE, 98+%
5-Quinolinecarboxaldehyde (8CI,9CI) | [EINECS(EC#)]
681-853-1 | [Molecular Formula]
C10H7NO | [MDL Number]
MFCD00805835 | [Molecular Weight]
157.17 | [MOL File]
22934-41-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
95-96°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 ]
solid | [pka]
3.94±0.12(Predicted) | [Appearance]
Yellow to brown Solid | [Water Solubility ]
Slightly soluble in water. | [Sensitive ]
Air Sensitive | [BRN ]
113095 | [InChI]
1S/C10H7NO/c12-7-8-3-1-5-10-9(8)4-2-6-11-10/h1-7H | [InChIKey]
BNEVFKZLYCGDFG-UHFFFAOYSA-N | [SMILES]
O=Cc1cccc2ncccc12 | [CAS DataBase Reference]
22934-41-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
WGK 3 | [HazardClass ]
IRRITANT | [HS Code ]
2933499090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Uses]
Quinoline-5-carboxaldehyde is used as a precursor in the preparation of pharmaceuticals. | [Synthesis]
General method: n-Butyllithium (2.5 M hexane solution, 300 μL, 0.72 mmol) was added slowly and dropwise to a solution of anhydrous THF (1.5 mL) of 5-bromoquinoline (100 mg, 0.48 mmol) at -78°C. The reaction solution turned red immediately. The reaction solution immediately turned red, followed by the addition of N,N-dimethylformamide (192 μL, 2.49 mmol). After maintaining the reaction temperature at -78 °C with stirring for 10 min, the reaction was quenched with deionized water (6 mL). The reaction mixture was poured into saturated aqueous sodium bicarbonate solution (10 mL) and extracted with ethyl acetate (3 × 10 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: n-hexane solution of 10% ethyl acetate) to give 5-quinolinecarboxaldehyde as a yellow solid in 53% yield. | [References]
[1] European Journal of Medicinal Chemistry, 2019, p. 290 - 320 |
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