Product Name

  • Name

    8-Hydroxyquinaldine

  • EINECS 212-562-6
  • CAS No. 826-81-3
  • Article Data36
  • CAS DataBase
  • Density 1.21 g/cm3
  • Solubility insoluble
  • Melting Point 71-73 °C(lit.)
  • Formula C10H9NO
  • Boiling Point 267 °C at 760 mmHg
  • Molecular Weight 159.188
  • Flash Point 139.4 °C
  • Transport Information UN 3077 9/PG 3
  • Appearance beige to brown crystalline powder
  • Safety 60-61-24/25-36-26
  • Risk Codes 50/53-36/37/38
  • Molecular Structure Molecular Structure of 826-81-3 (8-Hydroxyquinaldine)
  • Hazard Symbols IrritantXi,DangerousN
  • Synonyms 2-Methyl-8-hydroxyquinoline;2-Methyl-8-quinolinol;2-Methyloxine;Hydroxyquinaldine;
  • PSA 33.12000
  • LogP 2.24880

Synthetic route

trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With sulfuric acid; sodium iodide at 110℃; for 1h;95%
8-bromo-2-methylquinoline
61047-43-6

8-bromo-2-methylquinoline

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Inert atmosphere;95%
2-amino-phenol
95-55-6

2-amino-phenol

crotonaldehyde
123-73-9

crotonaldehyde

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With 2-hydroxynitrobenzene In sulfuric acid; acetic acid at 120℃; for 8h; Heating;94%
With sulfuric acid; water; 2-hydroxynitrobenzene oder in wss. Salzsaeure;
With hydrogenchloride; arsenic(V) oxide; water
ethylene glycol
107-21-1

ethylene glycol

2-amino-phenol
95-55-6

2-amino-phenol

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With tetrachloromethane; iron(III) chloride hexahydrate at 150℃; for 8h; Inert atmosphere; Sealed tube; Autoclave;88%
trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

2-amino-phenol
95-55-6

2-amino-phenol

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With phospho-tungstic acid; phosphotungstic acid; silica gel for 0.2h; Doebner-Miller reaction; microwave irradiation;85%
With hydrogenchloride at 90℃; for 5h;
2-amino-3-hydroxybenzaldehyde
1004545-97-4

2-amino-3-hydroxybenzaldehyde

acetone
67-64-1

acetone

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 130℃; for 0.666667h; Friedlaender Quinoline Synthesis; Microwave irradiation; Inert atmosphere;84%
4-(3-hydroxyphenyl)butan-2-one O-2,4-dinitrophenyloxime

4-(3-hydroxyphenyl)butan-2-one O-2,4-dinitrophenyloxime

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
Stage #1: 4-(3-hydroxyphenyl)butan-2-one O-2,4-dinitrophenyloxime With sodium hydride In 1,4-dioxane at 50℃; for 20h; Cyclization;
Stage #2: With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 2h; Oxidation; Heating;		80%
With sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1) dioxane, reflux, 0.5 h, 2) dioxane, reflux, 2 h; Yield given. Multistep reaction;
4-(3-hydroxyphenyl)butan-2-one (E)-O-2,4-dinitrophenyloxime

4-(3-hydroxyphenyl)butan-2-one (E)-O-2,4-dinitrophenyloxime

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
Stage #1: 4-(3-hydroxyphenyl)butan-2-one (E)-O-2,4-dinitrophenyloxime With sodium hydride In 1,4-dioxane at 50℃; for 20h; Cyclization;
Stage #2: With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 2h; Oxidation; Heating;		80%
8-chloroquinaldine
3033-82-7

8-chloroquinaldine

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; Inert atmosphere;79%
8-methoxy-2-methylquinoline
3033-80-5

8-methoxy-2-methylquinoline

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With hydrogen bromide for 36h; Inert atmosphere; Reflux;76%
chloroquinaldol
72-80-0

chloroquinaldol

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With palladium hydroxide 10 wt. % on activated carbon; hydrogen; triethylamine In ethanol at 43℃; under 9750.98 - 11251.1 Torr; for 6h; Solvent; Reagent/catalyst; Pressure;62.67%
ethanol
64-17-5

ethanol

2-amino-phenol
95-55-6

2-amino-phenol

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; oxygen; palladium diacetate; trifluoroacetic acid at 150℃; for 36h; Schlenk technique;58%
8-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline
81485-78-1

8-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; oxygen; nickel dibromide In tert-Amyl alcohol at 95℃; for 48h;56%
8-methoxy-2-methylquinoline
3033-80-5

8-methoxy-2-methylquinoline

methylamine
74-89-5

methylamine

A

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

B

8-methylaminoquinaldine
128278-09-1

8-methylaminoquinaldine

Conditions
ConditionsYield
With ammonium chloride In ethanol at 200℃; for 20h;A 30%
B 55%
...Expand
8-methoxy-2-methylquinoline
3033-80-5

8-methoxy-2-methylquinoline

A

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

B

8-methylaminoquinaldine
128278-09-1

8-methylaminoquinaldine

Conditions
ConditionsYield
With ammonium chloride; methylamine In ethanol at 200℃; for 20h;A 30%
B 55%
2-amino-3-(1-hydroxybut-3-enyl)phenol
1004545-76-9

2-amino-3-(1-hydroxybut-3-enyl)phenol

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With 1,10-Phenanthroline; air; palladium diacetate In methanol at 40℃; under 760.051 Torr; for 36h;53%
4-(3-hydroxyphenyl)butan-2-one (Z)-O-2,4-dinitrophenyloxime

4-(3-hydroxyphenyl)butan-2-one (Z)-O-2,4-dinitrophenyloxime

A

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

B

8-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline
81485-78-1

8-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane at 50℃; for 20h; Cyclization;A 36%
B 41%
4-(3-hydroxyphenyl)butan-2-one O-2,4-dinitrophenyloxime

4-(3-hydroxyphenyl)butan-2-one O-2,4-dinitrophenyloxime

A

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

B

8-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline
81485-78-1

8-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane for 0.5h; Heating;A 37%
B 33%
With sodium hydride In 1,4-dioxane for 0.5h; Product distribution; Heating; var. of base, no differences in reactions of the isolated (E)- and (Z)-isomers;A 37%
B 33%
4-(3-hydroxyphenyl)butan-2-one methylsulfonyl oxime

4-(3-hydroxyphenyl)butan-2-one methylsulfonyl oxime

A

6-hydroxyquinaldine
613-21-8

6-hydroxyquinaldine

B

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane for 0.5h; Heating;A 20%
B 7%
With air; sodium hydride In 1,4-dioxane at 50℃; for 20h; Cyclization;A 20%
B 7%
-butyl vinyl ether
111-34-2

-butyl vinyl ether

2-amino-phenol
95-55-6

2-amino-phenol

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With 1,4-dioxane; aniline hydrochloride
LACTIC ACID
849585-22-4

LACTIC ACID

2-amino-phenol
95-55-6

2-amino-phenol

2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With sulfuric acid
...Expand
2-amino-phenol
95-55-6

2-amino-phenol

paracetaldehyde
123-63-7

paracetaldehyde

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride; aluminium trichloride
quinaldine-sulfonic acid-(8)

quinaldine-sulfonic acid-(8)

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With potassium hydroxide
With potassium hydroxide
tetrakis(2-methyl-8-quinolinolato)thorium(IV) * 2-methyl-8-quinolinol
108348-16-9

tetrakis(2-methyl-8-quinolinolato)thorium(IV) * 2-methyl-8-quinolinol

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
70-155°C;
V2O3(meox)4

V2O3(meox)4

A

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

B

dioxo-2-methyl-8-quinolinolatovanadium(V)

dioxo-2-methyl-8-quinolinolatovanadium(V)

Conditions
ConditionsYield
With sodium hydroxide In neat (no solvent) VO(meox)2-O-VO(meox)2 heated in Abderhalden's dryer with sodium hydroxide as a trap for vaporized 8-quinolinol; complex recrystd. from chlorobenzene;
2-methyl-8-benzenesulfonyloxyquinoline
213881-38-0

2-methyl-8-benzenesulfonyloxyquinoline

A

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

B

benzenesulfonate
3198-32-1

benzenesulfonate

Conditions
ConditionsYield
In water-d2; [D3]acetonitrile at 25℃; pH=7.4; Quantum yield; HEPES buffer; UV-irradiation; Inert atmosphere;
2-methyl-8-quinolinyl-β-D-glucopyranoside
1419402-08-6

2-methyl-8-quinolinyl-β-D-glucopyranoside

A

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

B

β-D-glucose
492-61-5

β-D-glucose

Conditions
ConditionsYield
With β-glucosidase from almonds; water In aq. phosphate buffer at 37℃; for 4h; pH=7.4; Reagent/catalyst; Enzymatic reaction;
2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; sodium iodide / 6 h / 110 °C / Inert atmosphere
2: hydrogen bromide / 36 h / Inert atmosphere; Reflux
View Scheme
2-methylquinolin-8-yl [(L-leucyl)amino]propylsulfonate trifluoroacetate

2-methylquinolin-8-yl [(L-leucyl)amino]propylsulfonate trifluoroacetate

A

isothiazolidine 1,1-dioxide
5908-62-3

isothiazolidine 1,1-dioxide

B

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With Aeromonas proteolytica aminopeptidase; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid In dimethyl sulfoxide at 25℃; pH=8; Kinetics; Enzymatic reaction;
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

acetic anhydride
108-24-7

acetic anhydride

2‐methyl‐8‐acetoxyquinoline
27037-61-2

2‐methyl‐8‐acetoxyquinoline

Conditions
ConditionsYield
for 15h; Acetylation; Heating;100%
Reflux;99%
at 138℃; for 5h;95%
2-(3-bromomethyl-2,4-dichlorobenzenesulfonylamino)-2-methylpropionic acid tert-butyl ester
899797-70-7

2-(3-bromomethyl-2,4-dichlorobenzenesulfonylamino)-2-methylpropionic acid tert-butyl ester

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

2-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)benzenesulfonylamino]-2-methylpropionic acid tert-butyl ester
635697-85-7

2-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)benzenesulfonylamino]-2-methylpropionic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 2-methyl-8-quinolinol With sodium hydride In N,N-dimethyl-formamide
Stage #2: 2-(3-bromomethyl-2,4-dichlorobenzenesulfonylamino)-2-methylpropionic acid tert-butyl ester In N,N-dimethyl-formamide at 20℃;		100%
lithium borohydride

lithium borohydride

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

lithium tetra-(2-methyl-8-hydroxy-quinolinato)boron

lithium tetra-(2-methyl-8-hydroxy-quinolinato)boron

Conditions
ConditionsYield
In ethanol room temp., equiv. amts., pptn.;100%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

8-(methoxymethoxy)-2-methylquinoline
1262838-22-1

8-(methoxymethoxy)-2-methylquinoline

Conditions
ConditionsYield
Stage #1: 2-methyl-8-quinolinol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;		100%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

2-methyl-8-benzenesulfonyloxyquinoline
213881-38-0

2-methyl-8-benzenesulfonyloxyquinoline

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 1.5h;99%
With triethylamine In dichloromethane at 0 - 20℃; for 24.5h;97%
With triethylamine In benzene at 20 - 100℃;91%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2-methyl-8-quinolinyl trifluoromethanesulfonate
256652-07-0

2-methyl-8-quinolinyl trifluoromethanesulfonate

Conditions
ConditionsYield
With pyridine at 20℃; for 3h; triflation;99%
With pyridine In dichloromethane at 0 - 25℃; Inert atmosphere;98%
With 2,6-dimethylpyridine In dichloromethane at -20℃; for 1h;98%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

formaldehyd
50-00-0

formaldehyd

1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
23978-55-4

1,4,10,13-tetraoxa-7,16-diazacyclooctadecane

1,10-bis((2-methyl-8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ether
1245934-87-5

1,10-bis((2-methyl-8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ether

Conditions
ConditionsYield
In 1,4-dioxane for 2h; Product distribution / selectivity; Microwave irradiation;99%
In 1,4-dioxane for 2h; Mannich reaction; Inert atmosphere; Microwave irradiation;95%
...Expand
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

chloroquinaldol
72-80-0

chloroquinaldol

Conditions
ConditionsYield
With aluminum (III) chloride; N-chloro-succinimide In dichloromethane at 35℃; for 8h; Temperature; Solvent; Darkness; Green chemistry;98.8%
With hydrogenchloride; chlorine In water Reagent/catalyst; Inert atmosphere; Darkness;98.9%
With hydrogenchloride; sodium hypochlorite In water at 20 - 30℃; for 4.5h; Temperature;97.7%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

tetra(benzyl)hafnium
31406-67-4

tetra(benzyl)hafnium

(2-Me-8-quinolato)2Hf(CH2Ph)2

(2-Me-8-quinolato)2Hf(CH2Ph)2

Conditions
ConditionsYield
In toluene N2-atmosphere; stirring (room temp., 5 min); pptn. on concg. (vac., -40°C, 24 h), filtering;98.5%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

8-(cyclopropylmethoxy)-2-methylquinoline
1412254-56-8

8-(cyclopropylmethoxy)-2-methylquinoline

Conditions
ConditionsYield
With potassium carbonate In acetone at 88℃; for 48h; Sealed flask;98.5%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 13h;
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 13h;
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

benzyl bromide
100-39-0

benzyl bromide

2-methyl-8-(benzyloxy)quinoline
93315-49-2

2-methyl-8-(benzyloxy)quinoline

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 10h;98%
With sodium carbonate In ethanol; acetone at 20℃; for 12h; Darkness;90%
With sodium carbonate In ethanol; acetone at 20℃; for 12h; Inert atmosphere;90%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

5,7-dibromo-2-methylquinolin-8-ol
15599-52-7

5,7-dibromo-2-methylquinolin-8-ol

Conditions
ConditionsYield
With bromine In methanol at 20℃; for 0.0833333h;98%
With bromine; sodium hydrogencarbonate In methanol at 20℃; for 0.0833333h;97%
With bromine; sodium hydrogencarbonate In methanol at 20℃; for 0.0833333h;97%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

8-tert-butyldimethylsilyloxy-2-methyl-quinoline
171735-72-1

8-tert-butyldimethylsilyloxy-2-methyl-quinoline

Conditions
ConditionsYield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃;98%
With 1H-imidazole In dichloromethane at 20℃; for 10h;96%
With 1H-imidazole In dichloromethane
In dichloromethane
With 1H-imidazole In dichloromethane at 20℃; for 12h; Inert atmosphere;
indium(III) chloride

indium(III) chloride

2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

C30H24InN3O3

C30H24InN3O3

Conditions
ConditionsYield
With acetic acid In toluene for 0.25h; Inert atmosphere; Glovebox; Schlenk technique; Reflux;98%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

methyl iodide
74-88-4

methyl iodide

8-methoxy-2-methylquinoline
3033-80-5

8-methoxy-2-methylquinoline

Conditions
ConditionsYield
Stage #1: 2-methyl-8-quinolinol With potassium tert-butylate In tetrahydrofuran for 3h; Reflux; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;		97%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;97%
Stage #1: 2-methyl-8-quinolinol With triethylamine In acetone at 20℃; for 0.333333h;
Stage #2: methyl iodide In acetone at 20℃; for 8h; Darkness;		95%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

trimellitic Anhydride
552-30-7

trimellitic Anhydride

C19H11NO5

C19H11NO5

Conditions
ConditionsYield
In nitrobenzene at 175 - 180℃; for 3h;97%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

triethylaluminum
97-93-8

triethylaluminum

bis(2-methyl-8-quinolinolato)ethylaluminium

bis(2-methyl-8-quinolinolato)ethylaluminium

Conditions
ConditionsYield
In toluene to a toluene soln. of AlEt3 was added dropwise a toluene soln. of 2-methyl-8-quinolinol for 1 h, the mixt. was stirred at room temp. for 12 h (inert atm.); ppt. was washed with toluene and dried in vac.; elem. anal.;97%
In toluene byproducts: C2H6; (N2); Al(C2H5)3 in toluene added dropwise to a soln. of ligand, stirred for 12 h at 298 K; sepd., evapd. (vac.), washed (hexane), filtered, dried (vac.); elem. anal.;64%
In toluene Heating / reflux;
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

triethylaluminum
97-93-8

triethylaluminum

ethylbis(2-methyl-8-quinolinolato)aluminium

ethylbis(2-methyl-8-quinolinolato)aluminium

Conditions
ConditionsYield
In toluene (inert gas); reaction of aluminium compd. with quinolinol deriv. in ratio 1:2 in toluene; I. Yamaguchi, T. Iijima, T. Yamamoto, J. Orgamonet. Chem. 654 (2002) 229 (Erratum: J.Organomet. Chem. 658 (2002) 281); NMR;97%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

4-chloro-1-butanesulfonyl chloride
1633-84-7

4-chloro-1-butanesulfonyl chloride

C14H16ClNO3S

C14H16ClNO3S

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 5.5h;97%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

8-hydroxy-2-(d3)methylquinoline

8-hydroxy-2-(d3)methylquinoline

Conditions
ConditionsYield
With water-d2; benzoic acid at 120℃; for 4h;97%
With water-d2; benzoic acid at 120℃; for 8h; Inert atmosphere; Schlenk technique;
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

3,4-dichlorobenzaldehyde
6287-38-3

3,4-dichlorobenzaldehyde

2-[2-(3,4-dichlorophenyl)vinyl]quinoline-8-ol
694443-67-9

2-[2-(3,4-dichlorophenyl)vinyl]quinoline-8-ol

Conditions
ConditionsYield
In acetic anhydride at 120℃; for 20h; Inert atmosphere;96.9%
Multi-step reaction with 2 steps
1: 16 h / 130 °C / Inert atmosphere
2: pyridine; water / 3 h / 100 °C
View Scheme
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

thiophenol
108-98-5

thiophenol

8-hydroxy-2-benzenesulfonylmethylquinoline

8-hydroxy-2-benzenesulfonylmethylquinoline

Conditions
ConditionsYield
With dihydrogen peroxide In water at 20℃; for 2h; Irradiation;96%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

3,5-bis(trifluoromethyl)benzyl bromide
32247-96-4

3,5-bis(trifluoromethyl)benzyl bromide

8-((3,5-bis(trifluoromethyl)benzyl)oxy)-2-methylquinoline

8-((3,5-bis(trifluoromethyl)benzyl)oxy)-2-methylquinoline

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 20℃;96%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

2-methyl-8-aminoquinoline
18978-78-4

2-methyl-8-aminoquinoline

Conditions
ConditionsYield
With ammonium sulfate; ammonium hydroxide at 170℃; for 48h;95%
With ammonium hydroxide; 2H3N*O3S(2-)*H2O*2H(1+) at 170℃; for 48h;45%
With ammonium hydroxide; sodium hydrogensulfite at 200℃;
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

2-formyl oxine
14510-06-6

2-formyl oxine

Conditions
ConditionsYield
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 24h;95%
With selenium(IV) oxide In 1,4-dioxane; water at 80℃; for 24h; Inert atmosphere;90%
With selenium(IV) oxide In 1,4-dioxane; water at 60℃; for 12.5h; Reflux;86%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

tetrakis(trimethylsilylmethyl)zirconium(IV)
32665-18-2

tetrakis(trimethylsilylmethyl)zirconium(IV)

(2-Me-8-quinolato)2Zr(CH2SiMe3)2

(2-Me-8-quinolato)2Zr(CH2SiMe3)2

Conditions
ConditionsYield
In pentane; benzene N2-atmosphere; stirring (room temp., 1 h); evapn. (vac.);95%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

tert-butylphenylphosphinic acid chloride
4923-85-7

tert-butylphenylphosphinic acid chloride

2-methylquinolin-8-yl tert-butyl(phenyl)posphinate
1227180-24-6

2-methylquinolin-8-yl tert-butyl(phenyl)posphinate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 24h; Reflux; Inert atmosphere;95%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

phenyl N-tosyl imine
51608-60-7

phenyl N-tosyl imine

N-(2-(8-hydroxyquinolin-2-yl)-1-phenylethyl)-4-methylbenzenesulfonamide
1218989-08-2

N-(2-(8-hydroxyquinolin-2-yl)-1-phenylethyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In tetrahydrofuran at 120℃; for 24h; Inert atmosphere; screw-cap vial;95%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

1,3-bis-(bromomethyl)benzene
626-15-3

1,3-bis-(bromomethyl)benzene

1,3-bis-(2-methyl-8-quinolyloxymethyl)benzene
1369787-70-1

1,3-bis-(2-methyl-8-quinolyloxymethyl)benzene

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 4h;95%
Stage #1: 2-methyl-8-quinolinol With potassium carbonate In acetonitrile at 80℃; for 0.166667h;
Stage #2: 1,3-bis-(bromomethyl)benzene In acetonitrile at 80℃; for 12h;		80%
Stage #1: 2-methyl-8-quinolinol With potassium carbonate In acetonitrile at 80℃; for 0.166667h;
Stage #2: 1,3-bis-(bromomethyl)benzene In acetonitrile at 80℃; for 12h;		80%

8-Hydroxyquinaldine Consensus Reports

Reported in EPA TSCA Inventory.

8-Hydroxyquinaldine Specification

The CAS registry number of 8-Hydroxy-2-methylquinoline is 826-81-3. The IUPAC name is 2-methylquinolin-8-ol. Its EINECS registry number is 212-562-6. In addition, the molecular formula is C10H9NO and the molecular weight is 159.18. It is a kind of beige to brown crystalline powder and belongs to the classes of Quinolines, Quinazolines and derivatives; Alkylquinolines; Hydroxyquinolines; Quinolines.

Physical properties about this chemical are: (1)ACD/LogP: 2.33; (2)ACD/LogD (pH 5.5): 0.85; (3)ACD/LogD (pH 7.4): 0.93; (4)ACD/BCF (pH 5.5): 1.14; (5)ACD/BCF (pH 7.4): 1.39; (6)ACD/KOC (pH 5.5): 14.5; (7)ACD/KOC (pH 7.4): 17.61; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 22.12 Å2; (12)Index of Refraction: 1.666; (13)Molar Refractivity: 48.89 cm3; (14)Molar Volume: 131.4 cm3; (15)Polarizability: 19.38 ×10-24cm3; (16)Surface Tension: 54.9 dyne/cm; (17)Density: 1.21 g/cm3; (18)Flash Point: 139.4 °C; (19)Enthalpy of Vaporization: 52.54 kJ/mol; (20)Boiling Point: 267 °C at 760 mmHg; (21)Vapour Pressure: 0.00508 mmHg at 25°C.

Preparation of 8-Hydroxy-2-methylquinoline: it can be prepared by o-aminophenol and crotonylal. Firstly, mix o-aminophenol with o-nitrophenol. Then add hydrochloric acid and crotonylal with stirring. Heat it for 6 hours and steam out the o-nitrophenol by steam distillation. You can get the crude by alkalization, neutralization and steam distillation. At last, you can obtain the product via a series of vacuum distillation, recrystallization and purification.

8-Hydroxy-2-methylquinoline can be prepared by o-aminophenol and crotonylal

Uses of 8-Hydroxy-2-methylquinoline: it can be used as reagent for the analysis and extractant to determine manganese, palladium, gallium, indium, beryllium, etc. It also can be used as precipitant for the determination of zinc, magnesium, etc. In addition, it can be used to get 2-methyl-quinolin-8-ylamine. This reaction will need reagents (NH4)2SO4*H2O and NH3(aq.). The reaction time is 2 days at reaction temperature of 170 °C. The yield is about 95%.

8-Hydroxy-2-methylquinoline can be used to get 2-methyl-quinolin-8-ylamine

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. And it is very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. This material and its container must be disposed of as hazardous waste. In addition, you should avoid release to the environment and you can refer to special instructions safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc1cccc2ccc(nc12)C
(2)InChI: InChI=1/C10H9NO/c1-7-5-6-8-3-2-4-9(12)10(8)11-7/h2-6,12H,1H3
(3)InChIKey: NBYLBWHHTUWMER-UHFFFAOYAF

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