| Identification | More | [Name]
6-HYDROXYQUINOLINE | [CAS]
19315-93-6 | [Synonyms]
2,6-DIHYDROXYQUINOLINE
2,6-QUINOLINEDIOL
6-HYDROXY-2(1H)-QUINOLINONE
6-HYDROXY-2(H)-QUINOLINONE
6-HYDROXYQUINOLINE
6-QUINOLINOL
AKOS 222-06
QUINOLIN-6-OL
TIMTEC-BB SBB004117
6-hydroquinilinone
1,2-Dihydro-6-hydroxy-2-oxoquinoline
6-Hydroxy-1H-quinolin-2-one
6-Hydroxyquinoline-(1H)-2-one
2(1H)-Quinolinone, 6-hydroxy-
6-Hydroxy-1,2-dihydroquinoline-2-one | [EINECS(EC#)]
209-454-6 | [Molecular Formula]
C9H7NO | [MDL Number]
MFCD00047611 | [Molecular Weight]
145.16 | [MOL File]
19315-93-6.mol |
| Questions And Answer | Back Directory | [Synthesis]
Synthesis of compound (3): In a 100mL three-necked flask equipped with a gas absorption device and a reflux condenser, trans-4-methoxyphenylacrylic acid (17.8g, 0.10mol) and toluene (55mL) were added, and thionyl chloride (11.9g, 0.10mol) was added dropwise. The mixture was slowly heated to 70℃ and reacted at this temperature for 4 hours. After cooling, the excess thionyl chloride was removed by vacuum concentration. The residue was frozen to precipitate a light yellow solid, which was recrystallized from dichloromethane to give 17.3g of white crystals, with a yield of 88.0%. Synthesis of compound (4): 60 mL of tetrahydrofuran, 12.1 g of 4-aminophenylboronic acid (88.0 mmol), and 13.3 g of triethylamine (132.0 mmol) were added to a 250 mL three-necked flask. Compound (3) (17.3 g, 88.0 mmol) dissolved in tetrahydrofuran (70 mL) was added dropwise at -5 to 0 °C. After the addition was complete, the mixture was stirred at room temperature for 2 hours. The pH of the reaction solution was acidified to 2-3 with concentrated hydrochloric acid, and a large amount of white solid precipitated. The solid was filtered, washed with water until neutral, and dried to obtain 24.6 g of white solid product, with a yield of 94.1%. Synthesis of 6-hydroxy-2(1H)-quinolinone compound (1): Add the product from the previous step (24.6 g, 82.7 mmol) and 250 mL of toluene to a 500 mL three-necked flask, cool to 0 °C, add 32.2 g (4.2 mmol) of B(C6F5) and 15.4 g (115.8 mmol) of anhydrous aluminum trichloride in portions, slowly heat to 90 °C, continue stirring for 2 hours, pour the reaction solution into 800 mL of glacial hydrochloric acid solution to make the pH 2-3, stir for 1 hour, separate the layers, and retain the organic layer. Acetic acid (49.6 g, 0.827 mol) was added dropwise to the obtained organic layer, followed by the addition of 30% H₂O₂ (9.4 g, 82.7 mmol) solution at 0–10 °C. After the addition was complete, the mixture was kept at 0–10 °C for 1 hour, then stirred at room temperature for another hour. Sodium bisulfite solution was added dropwise to quench the peroxides. The organic layer was separated, washed once with saturated brine, and concentrated under reduced pressure. The crude solid was recrystallized from methanol to give 10.8 g of a white solid product, 6-hydroxy-2(1H)-quinolinone, with a yield of 80.7%, mp 300 °C, and a purity of 99.2%. |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
188-190 °C(lit.)
| [Boiling point ]
449.4±45.0 °C(Predicted) | [density ]
1.337±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
9.61±0.20(Predicted) | [color ]
Off-White to Pale Beige | [InChI]
InChI=1S/C9H7NO2/c11-7-2-3-8-6(5-7)1-4-9(12)10-8/h1-5,11H,(H,10,12) | [InChIKey]
AQLYZDRHNHZHIS-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(O)C=C2)C=CC1=O | [CAS DataBase Reference]
19315-93-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [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:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
VC4130000
| [F ]
8 | [HS Code ]
29334900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
6-Hydroxyquinoline-(1H)-2-one (cas# 19315-93-6) is a compound useful in organic synthesis. | [Definition]
ChEBI: Quinoline-2,6-diol is a dihydroxyquinoline that is quinoline in which the hydrogens at positions 2 and 6 are replaced by hydroxy groups. | [General Description]
2,6-Quinolinediol is a substituted quinoline compound. It has been prepared starting from 6-methoxyquinoline. It has been reported to be one of the UV-absorbing compounds (UAC) found in cow milk. |
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