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148-24-3 Usage

Chemical Properties

8-Hydroxyquinoline is a white to cream-colored crystal or crystalline powder that is insoluble in water or ether and freely soluble in ethanol, acetone, chloroform, benzene, and aqueous mineral acids. It readily forms stable metal chelates, which are soluble or precipitable in organic solvents, depending on the pH of the solution (Hollingshead, 1954).

Uses

8-Hydroxyquinoline has a wide variety of uses. Primarily because of their metal chelating properties, 8-hydroxyquinoline and its salts, halogenated derivatives, and metal complexes have been used as analytical reagents (Hollingshead, 1954) and as antimicrobial agents in medicine, fungicides, and insecticides (Harvey, 1975). It is also used as a preservative in cosmetics and tobacco, a chemical intermediate in dye synthesis (IARC, 1977), and a precipitating reagent for uranium and other radioactive metals in nuclear power plant liquid waste effluent. It is used in nuclear medicine with indium-111 (Davis et al., 1978).

Definition

ChEBI: 8-Hydroxyquinoline is a monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes. It has a role as an antibacterial agent, an iron chelator, an antiseptic drug and an antifungal agrochemical. It derives from a hydride of a quinoline.

Application

8-Hydroxyquinoline may be used as a chelating ligand in the preparation of tris-(8-hydroxyquinoline)aluminum (Alq3), an organic electroluminescent compound used in organic light-emitting devices (OLEDs).

Preparation

8-Hydroxyquinoline is synthesized from o-aminophenol by cyclization reaction. Add glycerin into the acid-resistant reaction pot, slowly add concentrated sulfuric acid under stirring, and simultaneously add o-aminophenol and o-nitrophenol in sequence, and add 65% of the total oleum first. Heat up to 125°C, stop heating, naturally heat up to 140°C, and wait until the temperature returns to 136°C. The rest of the oleum was continued to be added, maintaining the temperature at 137°C. After adding acid, keep warm for 4 hours, cool to below 100°C, pump into an acid-resistant pot containing 10 times the amount of water (calculated by o-aminophenol), stir, heat to 75-80°C, use 30% sodium hydroxide The solution was neutralized to pH 7-7.2. The precipitate is released while hot, cooled into a block, and sublimed under reduced pressure to obtain the finished product of 8-hydroxyquinoline.

Brand name

Aci-jel;Benzease;Chinosol;Cp-cap;Dermacid;Dermoplast;Fennosan h 30;Heriat;Hydroxybenoxopyridine;Medicone derma-hc;Oxykin;Oxyquinoline-rhp;Pedivol;Phenopyridine;Preconsol;Quinoderm;Quinoped;Quinophenol;Recta medicone-hc;Semori;Serohinol;Serorhinol;Superol;Trimo-san;Triva douch powder;Triva jel.

Therapeutic Function

Antiseptic

World Health Organization (WHO)

Halogenated hydroxyquinoline is structurally related to clioquinol. See WHO comment for clioquinol. (Reference: (WHODI) WHO Drug Information, 77.1, 9, 1977)

General Description

White to off-white or faintly yellow crystalline powder. Phenolic odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

8-Hydroxyquinoline darkens on exposure to light. 8-Hydroxyquinoline readily forms stable metal chelates. 8-Hydroxyquinoline is incompatible with strong oxidizers. 8-Hydroxyquinoline is also incompatible with many metal ions.

Hazard

Toxic by ingestion. Questionable carcinogen.

Biochem/physiol Actions

8-Hydroxyquinoline is a RNA synthesis inhibitor that acts as a fungicide against Trichophyton mentagrophytes, Myrothecium verrucaria, and Trichoderma viride. The antifungal mechanism of action is not clear but appears to be structurally related.

Clinical Use

8-Hydroxyquinoline (8HQ) is an intermediate of halogenated quinoline anti-amebic drugs, including quiniodoform, clioquinoline, diiodoquinoline and the like. These drugs exert anti-amebic effects by inhibiting intestinal commensal bacteria, and are effective against amoebic dysentery, but have no effect on extra-intestinal amoebic parasites.8HQ is a small planar molecule with a lipophilic effect and a metal chelating ability. As a result, 8HQ and its derivatives hold medicinal properties such as antineurodegenerative, anticancer, antioxidant, antimicrobial, anti-inflammatory, and antidiabetic activities.

Safety Profile

8-Hydroxyquinoline (8-HQ) may be a skin irritant in man. Hair depigmentation was seen in mice treated dermally. Dilute solutions were slightly irritating to the eyes of rabbits. In cases of human poisoning (by ingestion or by the administration of an enema containing 8-HQ or its sulphate), the kidney, liver and blood were the principal sites of toxic attack. Comprehensive studies involving repeated oral administration of 8-HQ to rodents failed to identify any particular sites for toxic attack and provided no convincing evidence of carcinogenicity. 8-HQ induced chromosomal damage in mammalian cells in culture (including human cells), but gave conflicting results in mice treated intraperitoneally. Both 8-HQ and its sulphate have induced mutagenicity in Ames bacterial tests and there was some evidence of mutagenic activity in mammalian cells treated in culture.

Purification Methods

Crystallise oxine from hot EtOH, acetone, pet ether (b 60-80o) or water. Crude oxine can be purified by precipitation of copper oxinate, followed by liberation of free oxine with H2S or by steam distillation after acidification with H2SO4. Store it in the dark. It forms complexes with many metals. [Manske et al. Can J Research 27F 359 1949, Phillips Chem Rev 56 271 1956, Beilstein 21 III/IV 1135, 21/3 V 252.]

Check Digit Verification of cas no

The CAS Registry Mumber 148-24-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 8 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 148-24:
(5*1)+(4*4)+(3*8)+(2*2)+(1*4)=53
53 % 10 = 3
So 148-24-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H

148-24-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (H0305)  8-Quinolinol  >99.0%(GC)(T)

  • 148-24-3

  • 25g

  • 143.00CNY

  • Detail
  • TCI America

  • (H0305)  8-Quinolinol  >99.0%(GC)(T)

  • 148-24-3

  • 500g

  • 720.00CNY

  • Detail
  • Alfa Aesar

  • (41272)  8-Hydroxyquinoline, ACS   

  • 148-24-3

  • 50g

  • 358.0CNY

  • Detail
  • Alfa Aesar

  • (41272)  8-Hydroxyquinoline, ACS   

  • 148-24-3

  • 250g

  • 903.0CNY

  • Detail
  • Alfa Aesar

  • (41272)  8-Hydroxyquinoline, ACS   

  • 148-24-3

  • 1kg

  • 3068.0CNY

  • Detail
  • Alfa Aesar

  • (A14720)  8-Hydroxyquinoline, 99%   

  • 148-24-3

  • 100g

  • 199.0CNY

  • Detail
  • Alfa Aesar

  • (A14720)  8-Hydroxyquinoline, 99%   

  • 148-24-3

  • 500g

  • 694.0CNY

  • Detail
  • Alfa Aesar

  • (A14720)  8-Hydroxyquinoline, 99%   

  • 148-24-3

  • 2500g

  • 2795.0CNY

  • Detail
  • Sigma-Aldrich

  • (32502)  8-Quinolinol  puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99% (perchloric acid titration)

  • 148-24-3

  • 32502-100G

  • 1,116.18CNY

  • Detail
  • Sigma-Aldrich

  • (252565)  8-Hydroxyquinoline  ACS reagent, 99%

  • 148-24-3

  • 252565-50G

  • 842.40CNY

  • Detail
  • Sigma-Aldrich

  • (252565)  8-Hydroxyquinoline  ACS reagent, 99%

  • 148-24-3

  • 252565-250G

  • 1,364.22CNY

  • Detail
  • Sigma-Aldrich

  • (252565)  8-Hydroxyquinoline  ACS reagent, 99%

  • 148-24-3

  • 252565-500G

  • 2,102.49CNY

  • Detail

148-24-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name quinolin-8-ol

1.2 Other means of identification

Product number -
Other names 8-Hydroxyquinoline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:148-24-3 SDS

148-24-3Synthetic route

8-Quinolinyl formate
77037-85-5

8-Quinolinyl formate

A

8-quinolinol
148-24-3

8-quinolinol

B

RhClCO(PPh3)2

RhClCO(PPh3)2

Conditions
ConditionsYield
With RhCl(PPh3)3 In benzene at 40℃; for 1h; Product distribution; primer deut. isotop eff.;A 100%
B n/a
1,2,3,4-tetrahydroquinolin-8-ol
6640-50-2

1,2,3,4-tetrahydroquinolin-8-ol

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With potassium tert-butylate In decane at 150℃; for 36h; Inert atmosphere; Schlenk technique;98%
With iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support In acetonitrile at 100℃; under 11251.1 Torr; for 24h; Autoclave;93%
With perylene diimide covalent immobilized to SiO2 nanospheres; air In N,N-dimethyl acetamide at 20℃; UV-irradiation;93%
Bis-<8-chinolinyl>-carbonat
52968-25-9

Bis-<8-chinolinyl>-carbonat

2-Amino-1,1,3,3-tetramethoxypropan
81494-56-6

2-Amino-1,1,3,3-tetramethoxypropan

A

8-quinolinol
148-24-3

8-quinolinol

B

2--1,1,3,3-tetramethoxypropan

2--1,1,3,3-tetramethoxypropan

Conditions
ConditionsYield
In chloroform 1.) r. t., 12 h, 2.) reflux, 10 h;A 97%
B 74%
2-amino-phenol
95-55-6

2-amino-phenol

glycerol
56-81-5

glycerol

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
Stage #1: glycerol With sulfuric acid; copper(II) sulfate; calcium oxide for 1h; Reflux;
Stage #2: 2-amino-phenol for 0.333333h; Skraup Quinoline Synthesis;
Stage #3: With 2-hydroxynitrobenzene at 130 - 140℃; Concentration;
96.31%
Stage #1: 2-amino-phenol With sulfuric acid; 2-hydroxynitrobenzene at 70℃; for 0.5h;
Stage #2: glycerol at 150℃; for 4h; Temperature;
91%
With sulfuric acid In water at 36 - 200℃; for 0.25h; Microwave irradiation; Sealed tube; Green chemistry;34%
With sulfuric acid; iodine
Stage #1: 2-amino-phenol; glycerol With sulfuric acid
Stage #2: With nitrobenzene
anthranilic acid
118-92-3

anthranilic acid

acrolein
107-02-8

acrolein

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
Stage #1: anthranilic acid; acrolein With hydrogenchloride; acetic acid; hydroquinone at 95 - 100℃; for 3h;
Stage #2: With chloropyridinecobaloxime(III); Eosin Y In water; acetonitrile at 20℃; for 3h; Microwave irradiation;
96.2%
2-amino-phenol
95-55-6

2-amino-phenol

acrolein
107-02-8

acrolein

2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With formic acid at 95 - 100℃; for 2h; Concentration; Molecular sieve;95.6%
7,8-Epoxy-7,8-dihydroquinoline
110288-09-0

7,8-Epoxy-7,8-dihydroquinoline

A

quinolin-7-ol
580-20-1

quinolin-7-ol

B

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With silica gel at 110℃; for 0.25h; isomerization;A 5%
B 95%
8-methoxymethoxy-quinoline

8-methoxymethoxy-quinoline

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry;94%
2-amino-phenol
95-55-6

2-amino-phenol

glycerol
56-81-5

glycerol

2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With nickel(III) oxide; sulfuric acid; acetic acid at 90℃; for 5h; Temperature;92.7%
With sulfuric acid; acetic acid
quinolin-8-yl trifluoromethanesulfonate
108530-08-1

quinolin-8-yl trifluoromethanesulfonate

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With caesium carbonate In toluene at 80℃; for 15h;92%
8-Hydroxyquinoline-N-oxide
1127-45-3

8-Hydroxyquinoline-N-oxide

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt; potassium iodide In ethanol at 20℃; for 1.16667h;90%
With lithium tetrafluoroborate In water; acetonitrile at 20℃; for 4h; Electrochemical reaction; Inert atmosphere;24 mg
8-((tert-butyldimethylsilyl)oxy)quinoline
222713-64-6

8-((tert-butyldimethylsilyl)oxy)quinoline

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With zinc tetrafluoroborate In water for 13h; Ambient temperature;89%
With potassium hydrogen difluoride In methanol at 20℃; for 2h;89%
5,7-diiodo-8-hydroxyquinoline
83-73-8

5,7-diiodo-8-hydroxyquinoline

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With piperidine; carbon monoxide; palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 52505.3 Torr; for 24h;83%
8-acetyloxyquinoline
2598-29-0

8-acetyloxyquinoline

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With water; poly(ethyleneimine) at 40℃; for 0.5h;82%
(AEDPH3)·(8-OQH)·(H2O)

(AEDPH3)·(8-OQH)·(H2O)

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With ammonia In water at 20℃; for 24h;80.6%
2-amino-phenol
95-55-6

2-amino-phenol

trimethyleneglycol
504-63-2

trimethyleneglycol

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With tetrachloromethane; iron(III) chloride hexahydrate at 150℃; for 8h; Inert atmosphere; Sealed tube;79%
With 2,4,6-trimethyl-pyridine; oxygen; palladium diacetate; trifluoroacetic acid at 150℃; for 16h; Schlenk technique;55%
quinoline
91-22-5

quinoline

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With i-Amyl alcohol; ozone In water at -0.1℃;78%
With dihydrogen peroxide; bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt In ethanol; water at 20℃; for 1h; regioselective reaction;55%
findet sich im Harn von Kaninchen nach peroraler Verabreichung;
iodo-8 quinoleine
1006-47-9

iodo-8 quinoleine

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With lithium salt of proline; tetrabutylammomium bromide; potassium hydroxide; copper dichloride In water at 120℃; for 0.666667h; Microwave irradiation; Green chemistry;78%
8-bromoquinoline
16567-18-3

8-bromoquinoline

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; tris-(dibenzylideneacetone)dipalladium(0); cesiumhydroxide monohydrate In 1,4-dioxane at 110℃; Inert atmosphere; Glovebox; Sealed tube;74%
2-(prop-2-yn-1-ylamino)phenol
23504-14-5

2-(prop-2-yn-1-ylamino)phenol

A

8-quinolinol
148-24-3

8-quinolinol

B

2-methylidene-3,4-dihydro-2H-1,4-benzoxazine
343270-95-1

2-methylidene-3,4-dihydro-2H-1,4-benzoxazine

Conditions
ConditionsYield
With potassium carbonate; gold(I) chloride In acetonitrile for 8h; Reflux;A 8%
B 72%
1,2,3,4-tetrahydroquinolin-8-ol
6640-50-2

1,2,3,4-tetrahydroquinolin-8-ol

nitrobenzene
98-95-3

nitrobenzene

A

8-quinolinol
148-24-3

8-quinolinol

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 58%
B 62%
1,2,3,4-tetrahydroquinolin-8-ol
6640-50-2

1,2,3,4-tetrahydroquinolin-8-ol

1-butyl-4-nitro-benzene
20651-75-6

1-butyl-4-nitro-benzene

A

8-quinolinol
148-24-3

8-quinolinol

B

4-Butylaniline
104-13-2

4-Butylaniline

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 62%
B 61%
8-quinolinylboronic acid
86-58-8

8-quinolinylboronic acid

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With oxygen; N-ethyl-N,N-diisopropylamine; [5,6]fullerene-C70 In chloroform; toluene at 20℃; for 12h; Irradiation;61%
5,7-diiodo-8-hydroxyquinoline
83-73-8

5,7-diiodo-8-hydroxyquinoline

A

8-quinolinol
148-24-3

8-quinolinol

B

5-iodoquinolin-8-ol
13207-63-1

5-iodoquinolin-8-ol

C

7-iodo-8-hydroxyquinoline
7385-89-9

7-iodo-8-hydroxyquinoline

Conditions
ConditionsYield
With carbon monoxide; glycine ethyl ester hydrochloride; palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; under 52505.3 Torr; for 24h;A 51%
B n/a
C n/a
1,2,3,4-tetrahydroquinolin-8-ol
6640-50-2

1,2,3,4-tetrahydroquinolin-8-ol

3-ethylnitrobenzene
7369-50-8

3-ethylnitrobenzene

A

8-quinolinol
148-24-3

8-quinolinol

B

m-ethylaniline
587-02-0

m-ethylaniline

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 50%
B 51%
acrylaldehyde diethyl acetal
3054-95-3

acrylaldehyde diethyl acetal

2-amino-phenol
95-55-6

2-amino-phenol

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With hydrogenchloride In water at 111℃; for 24h; Doebner-von Miller Reaction;41%
Propargylic aldehyde
624-67-9

Propargylic aldehyde

2-amino-phenol
95-55-6

2-amino-phenol

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; silver trifluoromethanesulfonate In toluene at 80℃; for 4h;40%
C19H15NO3
1245937-15-8

C19H15NO3

8-quinolinol
148-24-3

8-quinolinol

Conditions
ConditionsYield
at 650℃; Flash vacuum pyrolysis;34%
quinoline
91-22-5

quinoline

A

3-hydroxyquinoline
580-18-7

3-hydroxyquinoline

B

8-quinolinol
148-24-3

8-quinolinol

C

anthranilic acid
118-92-3

anthranilic acid

D

(5R,6S)-cis-5,6-dihydroxy-5,6-dihydroquinoline
112259-26-4

(5R,6S)-cis-5,6-dihydroxy-5,6-dihydroquinoline

Conditions
ConditionsYield
With Pseudomonas putidaA 13%
B 27%
C 27%
D 33%
biotransformation by Pseudomonas putida UV4; Further byproducts given;A 11 mg
B 23 mg
C 22 mg
D 32%
biotransformation by Pseudomonas putida UV4; Further byproducts given;A 11 mg
B 23 mg
C 22 mg
D 32 mg
8-quinolinol
148-24-3

8-quinolinol

allyl bromide
106-95-6

allyl bromide

8-Allyloxy-chinolin
7652-26-8

8-Allyloxy-chinolin

Conditions
ConditionsYield
With potassium carbonate In acetone for 24h; Heating;100%
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 25℃; for 4h;84%
With potassium carbonate In ethanol at 70℃; for 10h; regioselective reaction;84%
8-quinolinol
148-24-3

8-quinolinol

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

(E)-4-((8-hydroxyquinolin-5-yl)diazenyl)benzenesulfonic acid
574-70-9

(E)-4-((8-hydroxyquinolin-5-yl)diazenyl)benzenesulfonic acid

Conditions
ConditionsYield
Stage #1: 4-aminobenzene sulfonic acid With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25h;
Stage #2: 8-quinolinol With sodium hydroxide In water
100%
With hydrogenchloride; sodium nitrite
With hydrogenchloride; sodium hydroxide; ethylenediaminetetraacetic acid; sodium nitrite In ethanol for 0.0833333h;
8-quinolinol
148-24-3

8-quinolinol

8-Hydroxyquinoline-N-oxide
1127-45-3

8-Hydroxyquinoline-N-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane100%
With dihydrogen peroxide In water at 20℃; for 4h; Catalytic behavior;98%
With 3-chloro-benzenecarboperoxoic acid In Isopropyl acetate at 10 - 35℃; for 5.83333h; Green chemistry;98.2%
8-quinolinol
148-24-3

8-quinolinol

8-quinolinol-5-sulfonic acid
84-88-8

8-quinolinol-5-sulfonic acid

Conditions
ConditionsYield
With oleum at 20℃;100%
With sulfuric acid
With sulfuric acid at 180℃; im Rohr;
With sulfuric acid at 0 - 5℃; for 30h;
8-quinolinol
148-24-3

8-quinolinol

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

quinolin-8-yl trifluoromethanesulfonate
108530-08-1

quinolin-8-yl trifluoromethanesulfonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere;100%
With pyridine In dichloromethane at 0 - 20℃;99%
With pyridine In dichloromethane at 0 - 20℃;97%
8-quinolinol
148-24-3

8-quinolinol

(-)-diisopinocamphenylborane chloride
85116-37-6

(-)-diisopinocamphenylborane chloride

bis((1R)-2,66-trimethylbicyclo[3.1.1]hept-3-yl)borinic acid-8-quinolyl ester

bis((1R)-2,66-trimethylbicyclo[3.1.1]hept-3-yl)borinic acid-8-quinolyl ester

Conditions
ConditionsYield
In diethyl ether100%
8-quinolinol
148-24-3

8-quinolinol

5-azonia-4-hydroxy-1H+-napthalenium ion

5-azonia-4-hydroxy-1H+-napthalenium ion

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; antimony pentafluoride at 25℃;100%
With trifluorormethanesulfonic acid; cyclohexane; antimony pentafluoride at 20℃;
8-quinolinol
148-24-3

8-quinolinol

chromium(III) chloride
10025-73-7

chromium(III) chloride

mer-tris-(8-hydroxyquinolinate)chromium(III)

mer-tris-(8-hydroxyquinolinate)chromium(III)

Conditions
ConditionsYield
With ammonia In water prepn. from aq. CrCl3 soln. and a soln. of 8-hydroxy-quinoline (in CH3CO2H, neutralized by dropwise addn. of NH4OH (slight pptn.), cleared by heating, satd. with CO2 after cooling, adjusted to pH 4-8 with aq. NH3, heated for 1.5 h with stirring;; pptn., filtering hot, washing with hot H2O and drying at 110 °C;;100%
With NH3 In water prepn. from aq. CrCl3 soln. and a soln. of 8-hydroxy-quinoline (in CH3CO2H, neutralized by dropwise addn. of NH4OH (slight pptn.), cleared by heating, satd. with CO2 after cooling, adjusted to pH 4-8 with aq. NH3, heated for 1.5 h with stirring;; pptn., filtering hot, washing with hot H2O and drying at 110 °C;;100%
8-quinolinol
148-24-3

8-quinolinol

(C6H5)4C4Au(CH3COCHCOCH3)

(C6H5)4C4Au(CH3COCHCOCH3)

(C6H5)4C4Au(C9H6NO)
79171-11-2

(C6H5)4C4Au(C9H6NO)

Conditions
ConditionsYield
In diethyl ether To a suspn. of complex in ether was added stoichiometric amount of ligand, stirred for 1-2 h at room temp.;; recrystd. from CH2Cl2-n-hexane; elem. anal.;;100%
8-quinolinol
148-24-3

8-quinolinol

MoCl2(N(2,6-i-Pr2C6H3))2(1,2-dimethoxyethane)

MoCl2(N(2,6-i-Pr2C6H3))2(1,2-dimethoxyethane)

Mo(C6H3(C3H7)2)2(8-quinolinate)2*pentane

Mo(C6H3(C3H7)2)2(8-quinolinate)2*pentane

Conditions
ConditionsYield
With triethylamine In diethyl ether; benzene byproducts: (Et3NH)Cl; N2 atmosphere, addn. of Et3N and Et2O soln. of quinolinol compound to benzene soln. of Mo complex at room temp., stirring (18 h); removement of volatiles (vacuum), extn. (pentane), centrifugation, concn. of pentane layers; elem. anal.;100%
Conditions
ConditionsYield
at 80 - 100℃; under 0.000750075 Torr; for 1h; Time; Large scale;100%
8-quinolinol
148-24-3

8-quinolinol

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

(E)-4-((8-hydroxyquinolin-5-yl)diazenyl)benzoic acid
67940-27-6

(E)-4-((8-hydroxyquinolin-5-yl)diazenyl)benzoic acid

Conditions
ConditionsYield
Stage #1: 4-amino-benzoic acid With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25h;
Stage #2: 8-quinolinol With sodium hydroxide In water
100%
8-quinolinol
148-24-3

8-quinolinol

di-tert-butyl-diazodicarboxylate
870-50-8

di-tert-butyl-diazodicarboxylate

di-tert-butyl 1-(8-hydroxyquinolin-7-yl)hydrazinyl-1,2-dicarboxylate

di-tert-butyl 1-(8-hydroxyquinolin-7-yl)hydrazinyl-1,2-dicarboxylate

Conditions
ConditionsYield
Stage #1: 8-quinolinol With sodium hydride In tetrahydrofuran Inert atmosphere;
Stage #2: di-tert-butyl-diazodicarboxylate In tetrahydrofuran at -5 - 60℃; for 1.5h; Reagent/catalyst; Solvent; Time; Temperature; Inert atmosphere;
99.9%
8-quinolinol
148-24-3

8-quinolinol

di-isopropyl azodicarboxylate
2446-83-5

di-isopropyl azodicarboxylate

diisopropyl 1-(8-hydroxyquinolin-7-yl)hydrazinyl-1,2-dicarboxylate

diisopropyl 1-(8-hydroxyquinolin-7-yl)hydrazinyl-1,2-dicarboxylate

Conditions
ConditionsYield
Stage #1: 8-quinolinol With sodium hydride In tetrahydrofuran Inert atmosphere;
Stage #2: di-isopropyl azodicarboxylate In tetrahydrofuran at -5 - 60℃; for 1.5h; Reagent/catalyst; Solvent; Time; Temperature; Inert atmosphere;
99.7%
8-quinolinol
148-24-3

8-quinolinol

copper(ll) sulfate pentahydrate

copper(ll) sulfate pentahydrate

copper 8-hydroxyquinolinate
13014-03-4

copper 8-hydroxyquinolinate

Conditions
ConditionsYield
With sodium hydroxide In water at 40 - 90℃; for 1h;99.3%
8-quinolinol
148-24-3

8-quinolinol

broxyquinoline
521-74-4

broxyquinoline

Conditions
ConditionsYield
With bromine; sodium hydrogencarbonate In methanol at 20℃; for 0.0833333h;99%
With bromine In methanol at 20℃; for 0.0833333h;97%
Stage #1: 8-quinolinol With bromine; sodium hydrogencarbonate In methanol at 20℃; for 0.0833333h;
Stage #2: With sodium sulfite In methanol; water at 20℃;
97%
8-quinolinol
148-24-3

8-quinolinol

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

8-(4-nitrophenoxy)quinoline
116253-76-0

8-(4-nitrophenoxy)quinoline

Conditions
ConditionsYield
With copper(l) iodide; 2-carbomethoxy-3-hydroxyquinoxaline-di-N-oxide; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 12h; Schlenk technique; Inert atmosphere;99%
With potassium carbonate In dimethyl sulfoxide for 0.0833333h; Heating; microwave irradiation;94%
With PEG-400; sodium hydroxide In N,N-dimethyl-formamide for 15h; Etherification; Irradiation; microwave irradiation;54%
8-quinolinol
148-24-3

8-quinolinol

formaldehyd
50-00-0

formaldehyd

5-chloromethyl-8-hydroxyquinoline hydrochloride
4053-45-6

5-chloromethyl-8-hydroxyquinoline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 0 - 20℃; for 4h;99%
With hydrogenchloride In water at 0 - 20℃; for 8h;98%
With hydrogenchloride In water at 0 - 20℃; for 8h; Product distribution / selectivity;98%
8-quinolinol
148-24-3

8-quinolinol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

quinolin-8-yl methanesulfonate
916314-51-7

quinolin-8-yl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;99%
With triethylamine In dichloromethane at 0 - 20℃;94%
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry;85%
8-quinolinol
148-24-3

8-quinolinol

bis(cyclopentadienyl)hafnium dichloride
12116-66-4

bis(cyclopentadienyl)hafnium dichloride

(π-C5H5)Hf(C9H6NO)2Cl

(π-C5H5)Hf(C9H6NO)2Cl

Conditions
ConditionsYield
In triethylamine byproducts: {(C2H5)3NH}Cl; sublimation at 200 °C and 10E-1 Torr;;99%
In triethylamine byproducts: {(C2H5)3NH}Cl; sublimation at 200 °C and 10E-1 Torr;;99%
In triethylamine byproducts: {(C2H5)3NH}Cl;68%
In triethylamine byproducts: {(C2H5)3NH}Cl;68%
8-quinolinol
148-24-3

8-quinolinol

tin(II) chloride dihdyrate
10025-69-1

tin(II) chloride dihdyrate

bis(8-hydroxyquinolinate)tin(II)
12148-41-3

bis(8-hydroxyquinolinate)tin(II)

Conditions
ConditionsYield
In ethanol N2-atmosphere; pptn. on dropwise addn. of SnCl2 to ligand (room temp., stirring); washing (EtOH, water), drying (vac., 1 h);99%
8-quinolinol
148-24-3

8-quinolinol

pentamethylantimony
15120-50-0

pentamethylantimony

tetramethyl(8-oxyquinolinato)antimony(V)
22784-64-1

tetramethyl(8-oxyquinolinato)antimony(V)

Conditions
ConditionsYield
In toluene byproducts: CH4; refluxing Me5Sb and oxine in toluene for 24 h; evapn. of solvent in vacuo, elem. anal.;99%
8-quinolinol
148-24-3

8-quinolinol

nitridobis(1,3-diphenylpropane-1,3-dionate)chromium(V)
632323-52-5

nitridobis(1,3-diphenylpropane-1,3-dionate)chromium(V)

nitridobis(8-hydroxyquinolinate)chromium(V)
632323-51-4

nitridobis(8-hydroxyquinolinate)chromium(V)

Conditions
ConditionsYield
In acetonitrile addn. of chromium complex to a soln. of ligand in acetonitrile, reflux for 5 min; hot filtration, cooling; elem. anal.;99%
8-quinolinol
148-24-3

8-quinolinol

molybdenum(VI) tetrachloride oxide
55171-05-6, 13814-75-0

molybdenum(VI) tetrachloride oxide

MoOCl4*2(8-hydroxyquinoline)

MoOCl4*2(8-hydroxyquinoline)

Conditions
ConditionsYield
In tetrachloromethane MoOCl4 and equiv. amt. of 8-hydroxyquinoline in CCl4 at room temp.;99%
8-quinolinol
148-24-3

8-quinolinol

molybdenum(VI) tetrachloride oxide
55171-05-6, 13814-75-0

molybdenum(VI) tetrachloride oxide

MoOCl4*(8-hydroxyquinoline)

MoOCl4*(8-hydroxyquinoline)

Conditions
ConditionsYield
In tetrachloromethane MoOCl4 and equiv. amt. of 8-hydroxyquinoline in CCl4 at room temp.;99%
8-quinolinol
148-24-3

8-quinolinol

tungsten(VI) oxychloride
13520-78-0, 160797-03-5

tungsten(VI) oxychloride

WOCl4*2(8-hydroxyquinoline)

WOCl4*2(8-hydroxyquinoline)

Conditions
ConditionsYield
In tetrachloromethane WOCl4 and equiv. amt. of 8-hydroxyquinoline in CCl4 at room temp.;99%
8-quinolinol
148-24-3

8-quinolinol

tungsten(VI) oxychloride
13520-78-0, 160797-03-5

tungsten(VI) oxychloride

WOCl4*(8-hydroxyquinoline)

WOCl4*(8-hydroxyquinoline)

Conditions
ConditionsYield
In tetrachloromethane WOCl4 and equiv. amt. of 8-hydroxyquinoline in CCl4 at room temp.;99%
8-quinolinol
148-24-3

8-quinolinol

5-[(6-Bicyclo[2.2.1]hept-5-en-2-yl-hexylamino)-methyl]-quinolin-8-ol
511243-86-0

5-[(6-Bicyclo[2.2.1]hept-5-en-2-yl-hexylamino)-methyl]-quinolin-8-ol

diethylzinc
557-20-0

diethylzinc

(C7H9(CH2)6NHCH2C9H5NO)zinc(8-hydroxyquinoline)
796882-43-4

(C7H9(CH2)6NHCH2C9H5NO)zinc(8-hydroxyquinoline)

Conditions
ConditionsYield
In not given 1:1:1 molar ratio, ligand added to ZnEt2, followed by quinoline;99%
8-quinolinol
148-24-3

8-quinolinol

[(osmium)Cl2(PPh3)2(CHC(PPh3)CPhC(CH3)NH](BF4)

[(osmium)Cl2(PPh3)2(CHC(PPh3)CPhC(CH3)NH](BF4)

C56H46ClN2OOsP2(2+)*BF4(1-)

C56H46ClN2OOsP2(2+)*BF4(1-)

Conditions
ConditionsYield
In chloroform for 72h; Reflux; Schlenk technique; Inert atmosphere;99%

148-24-3Related news

TAME5OX, abiotic siderophore analogue to enterobactin involving 8-Hydroxyquinoline (cas 148-24-3) subunits: Thermodynamic and photophysical studies09/30/2019

The synthesis, thermodynamic and photophysical properties of trivalent metal complexes of biomimetic nonadentate analogue, 5,5′-(2-(((8-hydroxyquinolin-5-yl)methylamino)methyl)-2-methylpropane-1,3-diyl)bis(azanediyl)bis(methylene)diquinolin-8-ol (TAME5OX), have been described. Combination of ab...detailed

8-Hydroxyquinoline (cas 148-24-3) Based Multipodal Systems: Effect of Spatial Placement of 8-Hydroxyquinoline (cas 148-24-3) on Metal Ion Recognition09/28/2019

The complexation behaviors of tetrapod 1,2,4,5-tetrakis(8-hydroxyquinolinoxymethyl) benzene (1) and dipod 1,2-bis(8-hydroxyquinolinoxymethyl)benzene (2) have been determined by fluorescence spectroscopy in CH3CN–H2O (4:1) buffered at pH 6.9 [HEPES 10 mM] and by 1H NMR in CD3CN-CDCl3 (1:1) mixtu...detailed

148-24-3Relevant articles and documents

Hydrolysis of 8-quinolyl phosphate monoester: Kinetic and theoretical studies of the effect of lanthanide ions

Souza, Bruno S.,Brandao, Tiago A. S.,Orth, Elisa S.,Roma, Ana C.,Longo, Ricardo L.,Bunton, Clifford A.,Nome, Faruk

, p. 1042 - 1053 (2009)

8-Quinolyl phosphate (8QP) in the presence of the trivalent lanthanide ions (Ln = La, Sm, Eu, Tb, and Er) forms a [Ln ? 8QP]+ complex where the lanthanide ion catalyzes hydrolysis of 8QP. In reactions with Tb 3+ or Er3+, t

(AEDPH3)·(8-OQH)·(H2O): A yellow supramolecular plaster with ammonia adsorption and ammonia-induced discoloration properties

Tian, Di,Xiong, Juan,Liang, Xi-Chao,Deng, Jing,Yuan, Liang-Jie,Chen, Shuo-Ping

, p. 2732 - 2737 (2014)

A novel supramolecular plaster, namely (AEDPH3)·(8-OQH) ·(H2O) (1), is synthesized and characterized. This plaster is an organic acid-base compound, which shows a three-dimensional (3D) sandwich-type supramolecular network. It is a yellow gelling material with excellent mechanical properties superior to that of gypsum plaster. Moreover, the plaster can adsorb ammonia (NH3) effectively, and exhibits an interesting ammonia-induced discoloration property.

Photodegradation of quinoline in water

Kochany, Jan,Maguire, R. James

, p. 1097 - 1110 (1994)

The photodegradation kinetics of quinoline have been studied at 313 nm and in sunlight in organic-free water, lake water, and water containing several different solutes. The half-life of sunlight photodegradation is slightly shorter in lake water than in organic-free water (4-8%, depending upon the season). In near-surface lake water at 40° N latitude in summer, quinoline was predicted to degrade readily in sunlight, with a half-life of about 14 calendar days. The calculated half-life in winter was about 123 calendar days. The photodegradation of quinoline was accelerated significantly by NaNO3 and dissolved organic matter, two effective producers of hydroxyl radicals in aquatic environments. The rate was also faster at pH 4.5 than at pH 7.0. Two photoproducts were identified in low yield, 2-hydroxyquinoline and 8-hydroxyquinoline; prolonged irradiation appeared to destroy the aromatic nucleus.

Effect of Poly(diallyldimethylammonium Chloride) and of Poly(ethyleneimine) on the Esterolysis of 8-Acetoxyquinoline

Arcelli, Antonio,Concilio, Carlo

, p. 1327 - 1331 (1983)

The esterolysis of 8-acetoquinoline (8-AQ) in aqueous solution in the presence of an excess of poly(diallyldimethylammonium chloride) (PDDA) or poly(ethylenimine) (PEI) was investigated at 30 deg C.In the presence of PDDA hydrolysis takes place and the polyion does not affect the rate of the reaction.In the presence of PEI the ester undergoes aminolysis and saturation kinetics are observed.The pH dependence of kobs, the apparent first-order rate constant of esterolysis, can be explained on the basis of the pH dependence of pKapp and the degree of ionization of PEI.A Broensted relationship has already been found for the aminolysis of 8-AQ with primary and secondary amines of low molecular weight.By extending the relationship to the reaction between the polymeric amino groups in PEI and 8-AQ, we can quantitatively predict the pH dependence of kobs under saturation conditions, provided that the proper values of pKapp of the amino groups are considered.

Synthesis of quinolines by iron-catalyzed reaction of anilines with propane-1,3-diol

Khusnutdinov,Bayguzina,Aminov

, p. 2725 - 2727 (2015)

Quinoline and its derivatives were synthesized by cyclocondensation of anilines with propane-1,3-diol in 57-96% yield in the presence of iron-containing catalysts in carbon tetrachloride.

Solid-state structural transformations of two AgI supramolecular polymorphs to another polymer upon absorption of HNO3 vapors

Akhbari, Kamran,Morsali, Ali

, p. 2787 - 2789 (2013)

Solid-state structural transformation of two polymorphic forms of [Ag(8-HqH)(8-Hq)]n (1α and 1β, where 8-HqH = 8-hydroxyquinoline and 8-Hq- = 8-hydroxyquinolate) to {[Ag(8-HqH)2]NO3}n (2) has been observed upon solid-gas reaction of compounds 1α and 1β with HNO3 vapors. Solid-gas reaction of compound 2 with hydrated vapors of NH3 results in the formation of only the 1β polymorph, while solid-solid reaction of compound 2 with KOH results in the formation of a 1α and 1β mixture with chiral and achiral space groups of P212 121 and Pbcn, respectively.

Eswaranarayana, N.,Raghava Rao, Bh. S. V.

, p. 339 - 349 (1954)

Hecht, F.,Ehrmann, W.

, p. 98 - 103 (1935)

Moeller, T.,Ramaniah, M. V.

, p. 3946 - 3949 (1953)

-

Yasnitskii et al.

, (1976)

-

Tassel, J. H. van,Wendlandt, W. W.

, p. 813 - 816 (1959)

Electrochemical-induced hydroxylation of aryl halides in the presence of Et3N in water

Ke, Fang,Lin, Chen,Lin, Mei,Long, Hua,Wu, Mei,Yang, Li,Zhuang, Qinglong

supporting information, p. 6417 - 6421 (2021/08/03)

A thorough study of mild and environmentally friendly electrochemical-induced hydroxylation of aryl halides without a catalyst is presented. The best protocol consists of hydroxylation of different aryl iodides and aryl bromides by water solution in the presence of Et3N under air, affording the target phenols in good isolated yields. Moreover, aryl chlorides were successfully employed as substrates. This methodology also provides a direct pathway for the formation of deoxyphomalone, which displayed a significant anti-proliferation effect.

Geometric and electronic effects on the performance of a bifunctional Ru2P catalyst in the hydrogenation and acceptorless dehydrogenation of N-heteroarenes

Shao, Fangjun,Yao, Zihao,Gao, Yijing,Zhou, Qiang,Bao, Zhikang,Zhuang, Guilin,Zhong, Xing,Wu, Chuan,Wei, Zhongzhe,Wang, Jianguo

, p. 1185 - 1194 (2021/02/16)

The development of bifunctional catalysts for the efficient hydrogenation and acceptorless dehydrogenation of N-heterocycles is a challenge. In this study, Ru2P/AC effectively promoted reversible transformations between unsaturated and saturated N-heterocycles affording yields of 98% and 99%, respectively. Moreover, a remarkable enhancement in the reusability of Ru2P/AC was observed compared with other Ru-based catalysts. According to density functional theory calculations, the superior performance of Ru2P/AC was ascribed to specific synergistic factors, namely geometric and electronic effects induced by P. P greatly reduced the large Ru-Ru ensembles and finely modified the electronic structures, leading to a low reaction barrier and high desorption ability of the catalyst, further boosting the hydrogenation and acceptorless dehydrogenation processes.

Superhydrophobic nickel/carbon core-shell nanocomposites for the hydrogen transfer reactions of nitrobenzene and N-heterocycles

Duan, Zhiying,Liu, Fangfang,Pang, Shaofeng,Su, Qiong,Wang, Yanbin,Xie, Xin,Zhang, Ping,Zhang, Yujing,Zhou, Feng

, p. 1996 - 2010 (2020/04/07)

In this work, catalytic hydrogen transfer as an effective, green, convenient and economical strategy is for the first time used to synthesize anilines and N-heterocyclic aromatic compounds from nitrobenzene and N-heterocycles in one step. Nevertheless, how to effectively reduce the possible effects of water on the catalyst by removal of the by-product water, and to further introduce water as the solvent based on green chemistry are still challenges. Since the structures and properties of carbon nanocomposites are easily modified by controllable construction, a one step pyrolysis process is used for controllable construction of micro/nano hierarchical carbon nanocomposites with core-shell structures and magnetic separation performance. Using various characterization methods and model reactions the relationship between the structure of Ni?NCFs (nickel-nitrogen-doped carbon frameworks) and catalytic performance was investigated, and the results show that there is a positive correlation between the catalytic performance and hydrophobicity of catalysts. Besides, the possible catalytically active sites, which are formed by the interaction of pyridinic N and graphitic N in the structure of nitrogen-doped graphene with the surfaces of Ni nanoparticles, should be pivotal to achieving the relatively high catalytic performance of materials. Due to its unique structure, the obtained Ni?NCF-700 catalyst with superhydrophobicity shows extraordinary performances toward the hydrogen transfer reaction of nitrobenzene and N-heterocycles in the aqueous state; meanwhile, it was also found that Ni?NCF-700 still retained its excellent catalytic activity and structural integrity after three cycles. Compared with traditional catalytic systems, our catalytic systems offer a highly effective, green and economical alternative for nitrobenzene and N-heterocycle transformation, and may open up a new avenue for simple construction of structure and activity defined carbon nanocomposite heterogeneous catalysts with superhydrophobicity.

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