| Identification | More | [Name]
7-Hydroxy-1,2,3,4-tetrahydroquinoline | [CAS]
58196-33-1 | [Synonyms]
7-Hydroxy-1,2,3,4-Tetrahydro Quinolinoe
7-Hydroxy-1,2,3,4-tetrahydroquinoline
7-hydroxy-1,2,3,4-Tetrahydro-quinolin
1,2,3,4-Tetrahydro-quinolin-7-ol
1,2,3,4-Tetrahydro-7-quinolinol | [Molecular Formula]
C9H11NO | [MDL Number]
MFCD08063887 | [Molecular Weight]
149.19 | [MOL File]
58196-33-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
70-80 °C | [Boiling point ]
319.7±31.0 °C(Predicted) | [density ]
1.141±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Solid | [pka]
10.70±0.20(Predicted) | [color ]
Dark Orange to Very Dark Orange | [Stability:]
Light Sensitive | [InChI]
InChI=1S/C9H11NO/c11-8-4-3-7-2-1-5-10-9(7)6-8/h3-4,6,10-11H,1-2,5H2 | [InChIKey]
HJJRGZMJZDSMDB-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC(O)=C2)CCC1 | [CAS DataBase Reference]
58196-33-1(CAS DataBase Reference) | [EPA Substance Registry System]
58196-33-1(EPA Substance) |
| Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of 7-hydroxy-1,2,3,4-tetrahydroquinoline from 3,4-dihydro-7-hydroxy-2(1H)-quinolinone was as follows: 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (2.00 g, 12.26 mmol) was dissolved in tetrahydrofuran (THF, 20 mL) and the solution was cooled down to 0 °C. Subsequently, sodium borohydride (NaBH4, 1.07 g, 28.19 mmol) was added, and then iodine (I2, 3.42 g, 13.48 mmol) dissolved in THF (20 mL) was slowly added dropwise through the addition funnel to the reaction mixture. After installing the condenser, the reaction mixture was refluxed overnight. After completion of the reaction, the reaction mixture was neutralized with 3 M hydrochloric acid solution and then extracted three times with dichloromethane. The organic layers were combined and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a viscous yellow oil. Finally, the crude product was purified by fast column chromatography to afford 7-hydroxy-1,2,3,4-tetrahydroquinoline as a white crystalline solid (1.80 g, 98% yield). | [References]
[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 2, p. 650 - 654
[2] Angew. Chem., 2013, vol. 125, # 2, p. 678 - 682,5
[3] Chinese Chemical Letters, 2018, vol. 29, # 10, p. 1497 - 1499
[4] Organic Letters, 2011, vol. 13, # 23, p. 6196 - 6199
[5] Organic and Biomolecular Chemistry, 2013, vol. 11, # 24, p. 3954 - 3962 |
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