7-Hydroxy-1,2,3,4-tetrahydroquinoline Chemical Properties

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)

pka

10.70±0.20(Predicted)

form 

Solid

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

7-Quinolinol, 1,2,3,4-tetrahydro- (58196-33-1)

Safety Information

HS Code 

2933499090

7-Hydroxy-1,2,3,4-tetrahydroquinoline Usage And Synthesis

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

7-Hydroxy-1,2,3,4-tetrahydroquinoline(58196-33-1)Related Product Information

• CHLOROPHOSPHONAZO III
• Ethoxyquin
• 6-Hydroxy-2(1H)-3,4-dihydroquinolinone
• Quinhydrone
• 1,2,3,4-Tetrahydroquinoline
• 7-Hydroxyquinoline
• QUINOLINE SULPHATE
• Chrysin
• Isoquinoline
• 8-Hydroxyquinoline
• Quinclorac
• 7-Hydroxy-1,2,3,4-tetrahydroisoquinoline Hydrochloride
• 1,4-Dihydro-7-hydroxy-3(2H)-isoquinolinone
• 1,2,3,4-TETRAHYDRO-ISOQUINOLIN-7-OL
• SULFORHODAMINE 101
• Coumarin 314
• Coumarin 153
• 8-HYDROXYJULOLIDINE