Product Name

  • Name

    4-Hydroxyquinoline

  • EINECS 210-268-2
  • CAS No. 611-36-9
  • Article Data20
  • CAS DataBase
  • Density 1.188 g/cm3
  • Solubility soluble in alcohol, slightly soluble in water
  • Melting Point 200-202 °C(lit.)
  • Formula C9H7NO
  • Boiling Point 261.5 °C at 760 mmHg
  • Molecular Weight 145.161
  • Flash Point 122.3 °C
  • Transport Information
  • Appearance light yellow and off-white crystal powder
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 611-36-9 (4-Hydroxyquinoline)
  • Hazard Symbols IrritantXi
  • Synonyms Quinoline, 4-hydroxy-;4-Quinolinol;4-Hydroxy Quinoline;Kynurine;Quinolin-4-ol;4-Quinolinol (8CI,9CI);
  • PSA 33.12000
  • LogP 1.94040

Synthetic route

4-(phenylmethoxy)quinoline
101273-58-9

4-(phenylmethoxy)quinoline

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; ascorbic acid In water; acetonitrile at 20℃; for 1h; Schlenk technique; Irradiation; Inert atmosphere; chemoselective reaction;99%
4-hydroxy-3-quinoline carboxylic acid
34785-11-0

4-hydroxy-3-quinoline carboxylic acid

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
In diphenylether for 1h; Reflux;97%
7-chloro-1,2,3,4-tetrahydroquinolin-4-one
21617-15-2

7-chloro-1,2,3,4-tetrahydroquinolin-4-one

A

7-chloro-4-hydroxylquinoline
86-99-7

7-chloro-4-hydroxylquinoline

B

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
A 88.3%
B n/a
1-methanesulfonyl-4a,8a-dihydro-1H-quinolin-4-one

1-methanesulfonyl-4a,8a-dihydro-1H-quinolin-4-one

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.0833333h;72%
methanesulfonic acid quinolin-4-yl ester

methanesulfonic acid quinolin-4-yl ester

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.0833333h;68%
5-(N-phenyl)-aminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione
15568-92-0

5-(N-phenyl)-aminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
In tetrahydrofuran at 300℃; under 75007.5 Torr; for 0.025h; Gould-Jacobs type cyclization; Flash vacuum pyrolysis; Autoclave; regioselective reaction;60%
1-(2-isocyanophenyl)ethan-1-one
521270-78-0

1-(2-isocyanophenyl)ethan-1-one

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 6h; Reagent/catalyst; Solvent; chemoselective reaction;57%
Quinoline N-oxide
1613-37-2

Quinoline N-oxide

A

quinoline
91-22-5

quinoline

B

quinolin-4-ol
611-36-9

quinolin-4-ol

C

2,2'-biquinoline
119-91-5

2,2'-biquinoline

D

4-(quinolin-4-yl)quinoline
27080-08-6, 34281-95-3

4-(quinolin-4-yl)quinoline

Conditions
ConditionsYield
With naphthalene In tetrahydrofuran for 24h;A n/a
B 32%
C 20%
D n/a
...Expand
Quinoline N-oxide
1613-37-2

Quinoline N-oxide

dichloroacethyl chloride
79-36-7

dichloroacethyl chloride

A

2-(dichloromethyl)quinoline
4032-52-4

2-(dichloromethyl)quinoline

B

quinolin-4-ol
611-36-9

quinolin-4-ol

C

bis(2-quinolyl)dichloromethane
88237-18-7

bis(2-quinolyl)dichloromethane

Conditions
ConditionsYield
With triethylamine In chloroform 2 h, r.t; 9 h;A 12.4%
B 4.6%
C 5.4%
...Expand
Quinoline N-oxide
1613-37-2

Quinoline N-oxide

A

2-(dichloromethyl)quinoline
4032-52-4

2-(dichloromethyl)quinoline

B

quinolin-4-ol
611-36-9

quinolin-4-ol

C

bis(2-quinolyl)dichloromethane
88237-18-7

bis(2-quinolyl)dichloromethane

Conditions
ConditionsYield
With dichloroacethyl chloride; triethylamine In chloroform 2 h, r.t; 9 h;A 12.4%
B 4.6%
C 5.4%
...Expand
4(1H)-quinolinone
529-37-3

4(1H)-quinolinone

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
In chloroform Thermodynamic data; Equilibrium constant; ΔRGo, tests in solvents of different polarity;
2,3-dihydroquinolin-4(1H)-one
4295-36-7

2,3-dihydroquinolin-4(1H)-one

water
7732-18-5

water

palladium/charcoal

palladium/charcoal

quinolin-4-ol
611-36-9

quinolin-4-ol

...Expand
methanol
67-56-1

methanol

1-hydroxyquinoline-4(1H)-one
72812-97-6

1-hydroxyquinoline-4(1H)-one

Raney nickel

Raney nickel

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
Hydrogenation;
at 40 - 55℃; under 18387.7 Torr; Hydrogenation;
...Expand
tetrachloromethane
56-23-5

tetrachloromethane

1-hydroxyquinoline-4(1H)-one
72812-97-6

1-hydroxyquinoline-4(1H)-one

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

A

4-chloroquinoline
611-35-8

4-chloroquinoline

B

quinolin-4-ol
611-36-9

quinolin-4-ol

...Expand
1-hydroxyquinoline-4(1H)-one
72812-97-6

1-hydroxyquinoline-4(1H)-one

chloroform
67-66-3

chloroform

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

A

4-chloroquinoline
611-35-8

4-chloroquinoline

B

quinolin-4-ol
611-36-9

quinolin-4-ol

...Expand
1-hydroxyquinoline-4(1H)-one
72812-97-6

1-hydroxyquinoline-4(1H)-one

ethyl acetate
141-78-6

ethyl acetate

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

A

4-chloroquinoline
611-35-8

4-chloroquinoline

B

quinolin-4-ol
611-36-9

quinolin-4-ol

...Expand
kynuramine
363-36-0

kynuramine

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
With mouse brain monoamine oxidase-B Enzyme kinetics;
In aq. phosphate buffer at 37℃; for 0.333333h;
Kynuramine dihydrobromide

Kynuramine dihydrobromide

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
With human recombinant monoamine oxidase-A GST fusion protein; Soerensen-phosphate buffer at 30℃; Enzyme kinetics;
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

aniline
62-53-3

aniline

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
Stage #1: cycl-isopropylidene malonate With orthoformic acid triethyl ester at 145℃;
Stage #2: aniline at 50 - 145℃;
Stage #3: In diphenylether at 250℃;
4-chloroquinoline
611-35-8

4-chloroquinoline

quinolin-4-ol
611-36-9

quinolin-4-ol

kynuramine

kynuramine

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
With potassium chloride at 37℃; pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction;
aniline
62-53-3

aniline

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / 2 h / Reflux
2: tetrahydrofuran / 0.03 h / 300 °C / 75007.5 Torr / Flash vacuum pyrolysis; Autoclave
View Scheme
Multi-step reaction with 4 steps
1: 1 h / Reflux
2: diphenylether / 1 h / Reflux
3: sodium hydroxide / 1 h / Reflux
4: diphenylether / 1 h / Reflux
View Scheme
methylene blue
152071-32-4

methylene blue

Trp
54-12-6

Trp

A

tryptamine
61-54-1

tryptamine

B

quinolin-4-ol
611-36-9

quinolin-4-ol

C

2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid
1022-31-7

2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid

D

Kynurenine
343-65-7

Kynurenine

Conditions
ConditionsYield
With Saccharomyces cerevisiae wild type strain V328 for 0.333333h; UV-irradiation;
...Expand
naproxen
23981-80-8

naproxen

Trp
54-12-6

Trp

A

tryptamine
61-54-1

tryptamine

B

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
With Saccharomyces cerevisiae wild type strain V328 for 0.333333h; UV-irradiation;
...Expand
diethyl (anilinomethylene)malonate
54535-22-7

diethyl (anilinomethylene)malonate

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diphenylether / 1 h / Reflux
2: sodium hydroxide / 1 h / Reflux
3: diphenylether / 1 h / Reflux
View Scheme
ethyl 4-hydroxy-3-quinolinecarboxylate
26892-90-0

ethyl 4-hydroxy-3-quinolinecarboxylate

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / 1 h / Reflux
2: diphenylether / 1 h / Reflux
View Scheme
2-aminoacetophenone
551-93-9

2-aminoacetophenone

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 6 h / 20 °C
View Scheme
2-[(trimethylsilyl)ethynyl]aniline
103529-16-4

2-[(trimethylsilyl)ethynyl]aniline

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / methanol / 12 h / 20 °C
2: hydrogenchloride; cetyltrimethylammonim bromide / water / 12 h / 80 °C
4: copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 6 h / 20 °C
View Scheme
2-ethynylaniline
52670-38-9

2-ethynylaniline

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride; cetyltrimethylammonim bromide / water / 12 h / 80 °C
3: copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 6 h / 20 °C
View Scheme
2-iodophenylamine
615-43-0

2-iodophenylamine

quinolin-4-ol
611-36-9

quinolin-4-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
2: potassium carbonate / methanol / 12 h / 20 °C
3: hydrogenchloride; cetyltrimethylammonim bromide / water / 12 h / 80 °C
5: copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 6 h / 20 °C
View Scheme
quinolin-4-ol
611-36-9

quinolin-4-ol

3-bromo-4-hydroxyquinoline
64965-47-5

3-bromo-4-hydroxyquinoline

Conditions
ConditionsYield
With N-Bromosuccinimide In water; dimethyl sulfoxide for 24h;97%
With bromine; acetic acid
quinolin-4-ol
611-36-9

quinolin-4-ol

4-bromoquinoline
3964-04-3

4-bromoquinoline

Conditions
ConditionsYield
With boron tribromide In N,N-dimethyl-formamide Inert atmosphere;96%
With phosphorus tribromide In N,N-dimethyl-formamide at 20℃; for 0.5h;92%
With phosphorus tribromide In N,N-dimethyl-formamide for 0.666667h; Inert atmosphere;88%
quinolin-4-ol
611-36-9

quinolin-4-ol

4-methoxymethoxy-1-butanol
101992-89-6

4-methoxymethoxy-1-butanol

4-(4-methoxymethoxybutoxy)quinoline

4-(4-methoxymethoxybutoxy)quinoline

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;96%
quinolin-4-ol
611-36-9

quinolin-4-ol

4-hydroxy-6-nitro-quinoline
23432-42-0

4-hydroxy-6-nitro-quinoline

Conditions
ConditionsYield
With sulfuric acid; nitric acid In water at -15 - 20℃; for 3h;95%
With sulfuric acid; nitric acid at -15 - 0℃; for 2h;84%
Stage #1: quinolin-4-ol With sulfuric acid; nitric acid at 0 - 5℃; Cooling with ice;
Stage #2: at 20℃; for 2h;		63%
quinolin-4-ol
611-36-9

quinolin-4-ol

1,2-bis(4-methylphenyl)acetylene
2789-88-0

1,2-bis(4-methylphenyl)acetylene

5,6-di-p-tolylpyrano[2,3,4-de]quinoline

5,6-di-p-tolylpyrano[2,3,4-de]quinoline

Conditions
ConditionsYield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; lithium trifluoromethanesulfonate In 1,2-dimethoxyethane at 100℃; for 12h; Schlenk technique; Inert atmosphere;95%
quinolin-4-ol
611-36-9

quinolin-4-ol

benzoyl chloride
98-88-4

benzoyl chloride

4-(benzoyloxy)quinoline
81336-57-4

4-(benzoyloxy)quinoline

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane at 10 - 25℃;94%
With 4-methyl-morpholine In dichloromethane at 20℃; for 3h;
In dichloromethane at 20℃; for 3h;
quinolin-4-ol
611-36-9

quinolin-4-ol

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1-methanesulfonyl-4a,8a-dihydro-1H-quinolin-4-one

1-methanesulfonyl-4a,8a-dihydro-1H-quinolin-4-one

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 20℃; for 2h;94%
quinolin-4-ol
611-36-9

quinolin-4-ol

benzyl alcohol
100-51-6

benzyl alcohol

4-(phenylmethoxy)quinoline
101273-58-9

4-(phenylmethoxy)quinoline

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20 - 30℃; Mitsunobu Displacement; Inert atmosphere; regioselective reaction;94%

4-Hydroxyquinoline Chemical Properties

Molecule structure of 4-Hydroxyquinoline (CAS NO.611-36-9):

IUPAC Name: 1H-Quinolin-4-one
Molecular Formula: C9H7NO
Molecular Weight: 145.157980 g/mol
Density: 1.188 g/cm3
Melting Point: 202-206 °C
Boiling Point: 261.5 °C at 760 mmHg
Flash Point: 122.3 °C 
Index of Refraction: 1.595
Molar Refractivity: 41.5 cm3
Molar Volume: 122 cm3
Polarizability: 16.45×10-24 cm3
Surface Tension: 43.5 dyne/cm
Solubility: soluble in alcohol, slightly soluble in water
XLogP3: 0.6
H-Bond Donor: 1
H-Bond Acceptor: 2
Tautomer Count: 3
Exact Mass: 145.052764
MonoIsotopic Mass: 145.052764
Topological Polar Surface Area: 29.1
Heavy Atom Count: 11
Complexity: 198 
Canonical SMILES: C1=CC=C2C(=C1)C(=O)C=CN2
InChI: InChI=1S/C9H7NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-6H,(H,10,11)
InChIKey: PMZDQRJGMBOQBF-UHFFFAOYSA-N
EINECS:210-268-2
Product Categories: Alcohols and Derivatives; Heterocycles; Quinolines, Quinazolines and derivatives; Heterocyclic Series; Quinoline&Isoquinoline; Quinolines; Hydroxyquinolines; quinoline

4-Hydroxyquinoline Uses

 4-Hydroxyquinoline (611-36-9) is used for pharmaceutical intermediates.

4-Hydroxyquinoline Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: VC4070000

4-Hydroxyquinoline Specification

 4-Hydroxyquinoline (CAS NO.611-36-9) is also named as BRN 1524969 ; CCRIS 4329 ; Kynurine ; NSC 3183 ; Quinoline, 4-hydroxy- . 4-Hydroxyquinoline (CAS NO.611-36-9) is light beige to yellowish crystal powder or needles.

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