3-Hydroxyquinoline Chemical Properties

Melting point:

198-202°C

Boiling point:

264.27°C (rough estimate)

Density 

1.1555 (rough estimate)

refractive index 

1.4500 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

4.28(at 20℃)

form 

Crystalline Powder

color 

Beige

Water Solubility 

587.9mg/L(20 ºC)

InChI

InChI=1S/C9H7NO/c11-8-5-7-3-1-2-4-9(7)10-6-8/h1-6,11H

InChIKey

IQQDNMHUOLMLNJ-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2)C=C(O)C=1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

RTECS 

VC4050000

HS Code 

29334990

3-Hydroxyquinoline Usage And Synthesis

Chemical Properties

Beige crystalline powder

Uses

3-Hydroxyquinoline is a chemical reagent used in the preparation cyclic peptides with an antitumor functionality. Quinoline derivative as a result of the metabolism by cytochrome P 450.

Synthesis

General procedure for the synthesis of 3-hydroxyquinoline from quinoline-3-boronic acid: to a round-bottomed flask were added quinoline-3-boronic acid (1.0 mmol), CuSO4-5H2O (0.02 g, 0.1 mmol), CNT-Chit film (10.0 mg), KOH (0.17 g, 3.0 mmol) and deionized water (5.00 mL). The reaction mixture was stirred openly at room temperature for 24 hours. After completion of the reaction, the mixture was filtered and the solids were washed with deionized water. The filtrate was acidified to pH 2-3 with dilute aqueous hydrochloric acid and subsequently extracted with ether (3 x 10 mL). The organic phases were combined and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with an eluent ratio of 70% hexane/30% ethyl acetate (v/v) to afford 3-hydroxyquinoline (0.1433 g, 93% yield) as an off-white solid.

References

[1] Tetrahedron Letters, 2018, vol. 59, # 52, p. 4597 - 4601
[2] Journal of the American Chemical Society, 2018, vol. 140, # 13, p. 4623 - 4631
[3] Organic Letters, 2012, vol. 14, # 13, p. 3494 - 3497
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2536 - 2548
[5] Advanced Synthesis and Catalysis, 2018, vol. 360, # 10, p. 2013 - 2019

3-Hydroxyquinoline(580-18-7)Related Product Information

• 4-Hydroxyquinoline
• 2-Quinolinol
• 6-Hydroxyquinoline
• Quinhydrone
• 3-Chloroquinoline
• 7-Hydroxyquinoline
• 8-HYDROXYQUINOLINE BASE
• Disperse Yellow 54
• 3-Hydroxy-2-methyl-4-quinolinecarboxylic acid
• 8-Hydroxyquinaldine
• 2,4-Quinolinediol
• 2-AMINO-4-HYDROXYQUINOLINE HYDRATE
• Tris(8-hydroxyquinolinato)erbium
• Ethyl 6,7-difluoro-2-ethylmercapto-4-hydroxyquinoline-3-carboxylate
• 3-Chloro-4-hydroxy-1H-quinolin-2-one
• 8-Hydroxyquinoline potassium sulfate
• 2,4-DIHYDROXYQUINOLINE MONOSODIUM SALT
• 3-HYDROXYQUINOLINE-4-CARBOXYLIC ACID