5,7-Dibromoquinolin-8-ol supplier

Name
5,7-DIBROMO-8-HYDROXYQUINOLINE
EINECS 208-317-8
CAS No. 521-74-4
Article Data45
CAS DataBase
Density 2.052 g/cm³
Solubility
Melting Point 198-200 °C(lit.)
Formula C₉H₅Br₂NO
Boiling Point 370.5 °C at 760 mmHg
Molecular Weight 302.953
Flash Point 177.9 °C
Transport Information
Appearance almost white powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 5,7-Dibromo-8-hydroxyquinoline;5,7-Dibromo-8-quinolinol;Brodiar;Broxyquinolin;Colepur;Colipar;Dibromoksin;Dibromoxine;Dibromoxyquinoline;Fenilor;Intensopan;NSC 1810;NSC 74937;Paramiba;
PSA 33.12000
LogP 3.46540

Synthetic route

: 148-24-3
8-quinolinol

: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
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%

: 504-29-0
2-aminopyridine

: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
With dihydrogen peroxide; potassium bromide at 25℃; bromination by the enzyme chloroperoxidase from Caldariomyces fumago in buffered solution of pH 2.7;	79%

: 148-24-3
8-quinolinol

A: 1198-14-7
5-bromo-8-hydroxyquinoline

B: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
With tribromo-isocyanuric acid In acetonitrile at 20℃; regioselective reaction;	A 72% B 11%
With bromine; acetic acid

: 148-24-3
8-quinolinol

A: 521-74-4
broxyquinoline

B: 13019-32-4
7-bromo-8-hydroxyquinoline

Conditions

Conditions	Yield
With bromine In chloroform at 20℃; for 48h; Darkness;	A 37% B 51%

: 148-24-3
8-quinolinol

A: 1198-14-7
5-bromo-8-hydroxyquinoline

B: 521-74-4
broxyquinoline

C: 13019-32-4
7-bromo-8-hydroxyquinoline

Conditions

Conditions	Yield
With hydrogen bromide; isopentyl nitrite In dichloromethane at 20℃; for 16h;	A 15% B 70 % Spectr. C 15%

...Expand

: 36107-02-5
5,7-dibromo-8-aminoquinoline

: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
Diazotization.durch Kochen der Diazoniumsalz-Loesung mit Wasser;

: 7647-01-0
hydrogenchloride

: 5852-78-8
8-hydroxy-quinoline-5-carboxylic acid

: 7726-95-6
bromine

: 521-74-4
broxyquinoline

...Expand

: 7647-01-0
hydrogenchloride

: 101439-77-4
2-(8-hydroxy-quinoline-7-carbonyl)-benzoic acid

: 7726-95-6
bromine

: 521-74-4
broxyquinoline

...Expand

: 7726-95-6
bromine

: 13019-32-4
7-bromo-8-hydroxyquinoline

: 521-74-4
broxyquinoline

: 2598-30-3
8-hydroxyquinoline-5-carbaldehyde

: 7726-95-6
bromine

: 64-19-7
acetic acid

: 521-74-4
broxyquinoline

...Expand

5-bromo-8-oxy-quinoline: 5-bromo-8-oxy-quinoline

: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
With bromine; acetic acid
With chloroform; bromine

7-bromo-8-oxy-quinoline: 7-bromo-8-oxy-quinoline

: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
With bromine; acetic acid
With chloroform; bromine

8-oxy-quinoline-carboxylic acid-(5): 8-oxy-quinoline-carboxylic acid-(5)

: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
With hydrogenchloride; bromine

8-oxy-quinoline-carboxylic acid-(7): 8-oxy-quinoline-carboxylic acid-(7)

: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
With bromine; acetic acid

8-oxy-quinoline-sulfonic acid-(5): 8-oxy-quinoline-sulfonic acid-(5)

: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
With bromine
With phosphorus pentabromide

: 7647-01-0
hydrogenchloride

: 148-24-3
8-quinolinol

bromine water: bromine water

: 521-74-4
broxyquinoline

...Expand

: 148-24-3
8-quinolinol

: 7732-18-5
water

bromine water: bromine water

: 521-74-4
broxyquinoline

...Expand

bromo-addition product of 5-bromo-8-oxy-quinoline hydrobromide: bromo-addition product of 5-bromo-8-oxy-quinoline hydrobromide

: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
beim Aufbewahren an der Luft, beim Kochen mit Wasser oder beim Erhitzen im Rohr auf 180grad;

: 1555-94-8
8-ethoxyquinoline

: 7726-95-6
bromine

: 64-19-7
acetic acid

A: 101422-06-4
8-ethoxy-5-bromo-quinoline

B: 521-74-4
broxyquinoline

...Expand

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

: 7789-69-7
phosphorus pentabromide

A: 521-74-4
broxyquinoline

B 3.5.7-tribromo-8-oxy-quinoline: 3.5.7-tribromo-8-oxy-quinoline

...Expand

: 7726-95-6
bromine

: 19829-79-9
8-hydroxy-7-quinolinecarboxylic acid

A: 521-74-4
broxyquinoline

B 5-bromo-8-oxy-quinoline-carboxylic acid-(7): 5-bromo-8-oxy-quinoline-carboxylic acid-(7)

Conditions

Conditions	Yield
substance of Schmitt, Engelmann;

...Expand

: 56-23-5
tetrachloromethane

: 148-24-3
8-quinolinol

: 593-95-3
carbonyl dibromide

A: 521-74-4
broxyquinoline

B 5-bromo-8-oxy-quinoline: 5-bromo-8-oxy-quinoline

...Expand

: 148-24-3
8-quinolinol

bromine (l mol): bromine (l mol)

A: 521-74-4
broxyquinoline

B 5-bromo-8-oxy-quinoline: 5-bromo-8-oxy-quinoline

Conditions

Conditions	Yield
Reaktion des Hydrobromids; das entstehende rote Additionsprodukt uebergeht beim Aufbewahren unter Bromwasserstoff-Abspaltung;

...Expand

: 148-24-3
8-quinolinol

: 64-19-7
acetic acid

bromine (l mol): bromine (l mol)

A: 521-74-4
broxyquinoline

B 5-bromo-8-oxy-quinoline: 5-bromo-8-oxy-quinoline

...Expand

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

: 7726-95-6
bromine

A: 521-74-4
broxyquinoline

B 7-bromo-8-oxy-quinoline-sulfonic acid-(5): 7-bromo-8-oxy-quinoline-sulfonic acid-(5)

...Expand

: 7732-18-5
water

: 7726-95-6
bromine

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

: 521-74-4
broxyquinoline

...Expand

: 8-ethoxy-quinoline; tribromoide

A: 148-24-3
8-quinolinol

B: 521-74-4
broxyquinoline

C 5-bromo-8-oxy-quinoline: 5-bromo-8-oxy-quinoline

Conditions

Conditions	Yield
at 200℃;

...Expand

: 54250-31-6
tetrakis(5,7-dibromo-8-quinolinolato)thorium(IV) * 5,7-dibromo-8-quinolinol

A: 521-74-4
broxyquinoline

B: 107896-45-7
tetrakis(5,7-dibromo-8-quinolinolato)thorium(IV)

Conditions

Conditions	Yield
dissocn., 125-145°C;
dissocn., 125-145°C;

: 106-49-0
p-toluidine

: 521-74-4
broxyquinoline

Conditions

Conditions	Yield
With bromine

: 110-52-1
1,4-dibromo-butane

: 521-74-4
broxyquinoline

: 1026668-08-5
1,3-dibromo-7,8,9,10-tetrahydro-11-oxa-6a-azoniacycloocta[de]naphthalene bromide

Conditions

Conditions	Yield
With Amberlite IRA 402(OH) resin In water at 80℃; for 4h; Inert atmosphere;	98%
With Amberlite IRA 402(OH) In water at 30 - 80℃; Inert atmosphere;	98%

: 521-74-4
broxyquinoline

: 3137-63-1
4-chloro-2-(trichloromethyl)quinazoline

: 4-(5,7-dibromoquinolin-8-yloxy)-2-(trichloromethyl)quinazoline

Conditions

Conditions	Yield
With dmap In toluene at 130℃; for 1h; Microwave irradiation; Sealed tube;	98%

: 521-74-4
broxyquinoline

: 106-93-4
ethylene dibromide

: 1231156-93-6
7,9-dibromo-2,3-dihydro-1-oxa-3a-azonia-phenalene bromide

Conditions

Conditions	Yield
With Amberlite IRA 402(OH) resin In water at 80℃; for 3h; Inert atmosphere;	97%
With Amberlite IRA 402(OH) In water at 30 - 80℃; Inert atmosphere;	97%

: 527-69-5
2-furancarbonyl chloride

: 521-74-4
broxyquinoline

: C14H7Br2NO3

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	96%

: 3138-86-1
2,3-bis(bromomethyl)quinoxaline

: 521-74-4
broxyquinoline

: 5720-07-0
4-methoxyphenylboronic acid

: 1190620-41-7
4,6-bis(4-methoxyphenyl)-8,15-dihydro-1H-quinolino[8′,1′:2,3,4]-[1,4]oxazocino[6,7-b]quinoxalin-1-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In ethanol; water at 20℃; for 24h; Irradiation; Inert atmosphere;	96%

...Expand

: 521-74-4
broxyquinoline

: 77-78-1
dimethyl sulfate

: 17012-49-6
5,7-dibromo-8-methoxyquinoline

Conditions

Conditions	Yield
Stage #1: broxyquinoline With potassium carbonate In acetone for 0.5h; Reflux; Stage #2: dimethyl sulfate In acetone for 24h; Reflux;	95.6%

: 521-74-4
broxyquinoline

: 106-93-4
ethylene dibromide

: 8,10-dibromo-2H,3H,5H-1,4-oxazino[6,5,4-i,j]quinolin-5-one

Conditions

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	95%

: 521-74-4
broxyquinoline

: 1420334-85-5
and ethyl 2-(bromomethyl)benzo[h]quinoline-3-carboxylate

: 1420335-11-0
ethyl 2-((5,7-dibromoquinolin-8-yloxy)methyl)benzo[h]quinoline-3-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 4h; Williamson Ether Synthesis; Reflux;	95%

: 521-74-4
broxyquinoline

: 52462-29-0
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

: [(η6-pcymene)RuCl(k2-O,N-5,7-dibromo-(8-hydroxy quinoline))]Cl

Conditions

Conditions	Yield
In methanol at 20℃; for 0.5h;	95%

: 3138-86-1
2,3-bis(bromomethyl)quinoxaline

: 521-74-4
broxyquinoline

: 5720-05-8
4-methylphenylboronic acid

: 1190620-42-8
4,6-di-(p-tolyl)-8,15-dihydro-1H-quinolino[8′,1′:2,3,4][1,4]- oxazocino[6,7-b‑z]quinoxalin-1-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In ethanol; water at 20℃; for 24h; Irradiation; Inert atmosphere;	95%

...Expand

: 110-52-1
1,4-dibromo-butane

: 521-74-4
broxyquinoline

: 1026668-09-6
1,3-dibromo-7,8,9,10-tetrahydro-11-oxa-6a-azoniacycloocta[de]naphthalen-6-one

Conditions

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	94%
With tert.-butylhydroperoxide; eosin y In ethanol; water at 20℃; for 24h; Inert atmosphere; Irradiation;

: 521-74-4
broxyquinoline

: 52462-29-0
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

: chlorido(5,7-dibromo-8-quinolinolato-κN1,κO8)(η6-p-cymene)ruthenium(II)

Conditions

Conditions	Yield
In methanol; dichloromethane at 65℃; for 6h; Reflux;	92.3%
With sodium methylate In methanol; chloroform at 20℃; for 1h; Inert atmosphere; Schlenk technique;	76%

: 521-74-4
broxyquinoline

: 111571-60-9
ethyl 2-bromomethyl-3-quinoline-3-carboxylate

: 2-[(5,7-dibromoquinolin-8-yloxy)methyl]quinoline-3-carboxylicacid

Conditions

Conditions	Yield
Stage #1: broxyquinoline; ethyl 2-bromomethyl-3-quinoline-3-carboxylate With potassium carbonate In acetonitrile for 3h; Williamson Ether Synthesis; Reflux; Stage #2: With potassium hydroxide In ethanol; water for 2h; Williamson Ether Synthesis; Reflux;	92%

: 3138-86-1
2,3-bis(bromomethyl)quinoxaline

: 521-74-4
broxyquinoline

: 98-80-6
phenylboronic acid

: 1190620-40-6
4,6-diphenyl-8,15-dihydro-1H-quinolino[8′,1′:2,3,4][1,4]oxazocino[6,7-b]quinoxalin-1-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In ethanol; water at 20℃; for 24h; Reagent/catalyst; Solvent; Irradiation; Inert atmosphere;	92%

...Expand

: 3138-86-1
2,3-bis(bromomethyl)quinoxaline

: 521-74-4
broxyquinoline

: 197958-29-5
pyridin-2-ylboronic acid

: 4,6-di(pyridin-2-yl)-8,15-dihydro-1H-quinolino[8′,1′:2,3,4][1,4]oxazocino[6,7-b]-quinoxalin-1-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In ethanol; water at 20℃; for 24h; Irradiation; Inert atmosphere;	92%

...Expand

: 521-74-4
broxyquinoline

: 111571-60-9
ethyl 2-bromomethyl-3-quinoline-3-carboxylate

: 1420334-93-5
ethyl 2-((5,7-dibromoquinolin-8-yloxy)methyl)quinoline-3-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 4h; Williamson Ether Synthesis; Reflux;	91%

: 521-74-4
broxyquinoline

: 74-88-4
methyl iodide

: 17012-49-6
5,7-dibromo-8-methoxyquinoline

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In tetrahydrofuran for 35h;	90%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 5h;	89%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In tetrahydrofuran; water at 40℃;	78%

: 521-74-4
broxyquinoline

: 773-76-2
chloroxine

Conditions

Conditions	Yield
With pyridine hydrochloride at 220℃; for 0.166667h;	90%
With hydrogenchloride at 160 - 170℃;

: 521-74-4
broxyquinoline

: 97-00-7
1-chloro-2,4-dinitro-benzene

: 84165-49-1
5,7-dibromo-8-(2,4-dinitro-phenoxy)-quinoline

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 70℃; for 4h;	90%

: 521-74-4
broxyquinoline

: 638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3
manganese(II) acetate

: 14495-08-0
5,7-dibromo-8-hydroxyquinolinato manganese(II)

Conditions

Conditions	Yield
In tetrahydrofuran; water 1 M aq. Mn(OAc)2 (5 ml) added dropwise to soln. of 5,7-dibromo-8-hydroxyquinoline (10 mmol); refluxed (2 h); ppt. filtered; washed with EtOH; dried in air;	90%

: 3138-86-1
2,3-bis(bromomethyl)quinoxaline

: 521-74-4
broxyquinoline

: 1182708-31-1
5,7-dibromoquinolonoquinoxalino-oxazocine

Conditions

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	90%
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 10h;	88%

: 521-74-4
broxyquinoline

: 3298-98-4
2,3-Bis(bromomethyl)-6,7-dimethylquinoxaline

: 1182708-27-5
C21H15Br2N3O2

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 12h;	90%
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	90%

: 521-74-4
broxyquinoline

: 109-64-8
1,3-dibromo-propane

: 1026668-06-3
1,3-dibromo-8,9-dihydro-7H-10-oxa-6a-azacyclohepta[de]naphthalen-6-one

Conditions

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	90%
With tert.-butylhydroperoxide; eosin y In ethanol; water at 20℃; for 24h; Inert atmosphere; Irradiation;

: 521-74-4
broxyquinoline

: 91-13-4
α,α'-dibromo-o-xylene

: 1187578-29-5
C17H11Br2NO2

Conditions

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 1h;	90%

: 521-74-4
broxyquinoline

: 111-83-1
1-bromo-octane

: C17H21Br2NO

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 13h; Inert atmosphere;	90%

: 13331-23-2
fur-2-ylboronic acid

: 3138-86-1
2,3-bis(bromomethyl)quinoxaline

: 521-74-4
broxyquinoline

: 1190620-45-1
4,6-di(furan-2-yl)-8,15-dihydro-1H-quinolino[8′,1′:2,3,4][1,4]oxazocino[6,7-b]-quinoxalin-1-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In ethanol; water at 20℃; for 24h; Irradiation; Inert atmosphere;	90%

...Expand

: 3138-86-1
2,3-bis(bromomethyl)quinoxaline

: 521-74-4
broxyquinoline

: 32316-92-0
naphthalene-2-boronic acid

: 1190620-47-3
4,6-di(naphthalen-2-yl)-8,15-dihydro-1H-quinolino[8′,1′:2,3,4][1,4]oxazocino-[6,7-b]-quinoxalin-1-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In ethanol; water at 20℃; for 24h; Irradiation; Inert atmosphere;	90%

...Expand

: 3138-86-1
2,3-bis(bromomethyl)quinoxaline

: 521-74-4
broxyquinoline

: 13922-41-3
1-Naphthylboronic acid

: 1190620-48-4
4,6-di(naphthalen-1-yl)-8,15-dihydro-1H-quinolino[8′,1′:2,3,4][1,4]oxazocino[6,7-b]-quinoxalin-1-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In ethanol; water at 20℃; for 24h; Irradiation; Inert atmosphere;	90%

...Expand

: 521-74-4
broxyquinoline

: 5,7-dibromo-1,2,3,4-tetrahydroquinolin-8-ol

Conditions

Conditions	Yield
With hydrogen; dihydrogen hexachloroplatinate In water; isopropyl alcohol at 90 - 95℃; under 15001.2 Torr;	89%
With ammonia borane; tris(pentafluorophenyl)borate In toluene at 80℃; for 8h; Schlenk technique; Inert atmosphere;	70%

5,7-Dibromoquinolin-8-ol Chemical Properties

IUPAC Name:   5,7-Dibromoquinolin-8-ol
Synonyms：  5, 7-Dibromo-8-quinolinol ; 5, 7-Dibromoquinolin-8-ol ; 5,7-Dibromo-8-Hydroxyquinoline ; 5,7-dibromo-8-quinolinol ; 5,7-Dibromooxine ; 5,7-Dibromo-oxine
The Molecular Formula of 5, 7-Dibromo-8-quinolinol (521-74-4) :C₉H₅Br₂NO
The Molecular Weight of   5, 7-Dibromo-8-quinolinol (521-74-4):302.9501 g/mol
The Molecular Structure of 5, 7-Dibromo-8-quinolinol (521-74-4):
Index of Refraction: 1.738
Molar Refractivity: 59.44 cm³
Molar Volume: 147.5 cm³
Polarizability: 10^-24cm³
Surface Tension: 66.4 dyne/cm
Density: 2.052 g/ cm³
Flash Point: 177.9 °C
Enthalpy of Vaporization: 64.17 kJ/mol
Boiling Point: 370.5 °C at 760 mmHg
Vapour Pressure: 5.15E-06 mmHg at 25°C

5,7-Dibromoquinolin-8-ol Uses

5, 7-Dibromo-8-quinolinol (521-74-4) can be used as analytical reagent.

5,7-Dibromoquinolin-8-ol Toxicity Data With Reference

1.	orl-chd TDLo:1000 mg/kg/27D:CNS,PUL	LANCAO Lancet. 1 (1968),922.
2.	orl-rat LDLo:10 g/kg	KSRNAM Kiso to Rinsho. Clinical Report. 4 (1970),27.
3.	ipr-rat LD50:1140 mg/kg	KSRNAM Kiso to Rinsho. Clinical Report. 4 (1970),27.
4.	orl-mus LD50:7420 mg/kg	KSRNAM Kiso to Rinsho. Clinical Report. 4 (1970),27.
5.	ipr-mus LD50:325 mg/kg	KSRNAM Kiso to Rinsho. Clinical Report. 4 (1970),27.

5,7-Dibromoquinolin-8-ol Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

5,7-Dibromoquinolin-8-ol Safety Profile

Poison by intraperitoneal route. Mildly toxic by ingestion. Human systemic effects by ingestion: muscle weakness, ataxia (loss of muscle coordination), and gastritis. When heated to decomposition it emits very toxic fumes of Br⁻ and NO_x.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
WGK Germany: 2

Product Name

5,7-DIBROMO-8-HYDROXYQUINOLINE

Synthetic route

5,7-Dibromoquinolin-8-ol Chemical Properties

5,7-Dibromoquinolin-8-ol Uses

5,7-Dibromoquinolin-8-ol Toxicity Data With Reference

5,7-Dibromoquinolin-8-ol Consensus Reports

5,7-Dibromoquinolin-8-ol Safety Profile

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