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8-Hydroxyquinaldine

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Name

8-Hydroxyquinaldine

EINECS 212-562-6
CAS No. 826-81-3 Density 1.21 g/cm3
PSA 33.12000 LogP 2.24880
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;

Article Data 36

8-Hydroxyquinaldine Synthetic route

123-73-9

trans-Crotonaldehyde

90-04-0

2-methoxy-phenylamine

826-81-3

2-methyl-8-quinolinol

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

8-bromo-2-methylquinoline

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%
95-55-6

2-amino-phenol

123-73-9

crotonaldehyde

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
107-21-1

ethylene glycol

95-55-6

2-amino-phenol

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%
123-73-9

trans-Crotonaldehyde

95-55-6

2-amino-phenol

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;
1004545-97-4

2-amino-3-hydroxybenzaldehyde

67-64-1

acetone

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

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

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%
3033-82-7

8-chloroquinaldine

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%
3033-80-5

8-methoxy-2-methylquinoline

826-81-3

2-methyl-8-quinolinol

Conditions
ConditionsYield
With hydrogen bromide for 36h; Inert atmosphere; Reflux;76%

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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