Benzo[f]quinoline supplier

Name
5,6-BENZOQUINOLINE
EINECS
CAS No. 85-02-9
Article Data35
CAS DataBase
Density 1.187g/cm³
Solubility Insoluble in water
Melting Point 89-91 °C
Formula C13H9 N
Boiling Point 349 °C (721 mmHg)
Molecular Weight 179.221
Flash Point 166 °C
Transport Information
Appearance BROWN CRYSTALLINE POWDER
Safety Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
Risk Codes 40-36/37/38
Molecular Structure
Hazard Symbols
Synonyms 1-Azaphenanthrene;5,6-Benzo[f]quinoline; 5,6-Benzoquinoline; NSC 9850; b-Naphthoquinoline
PSA 12.89000
LogP 3.38800

Synthetic route

: 17104-69-7
5,6-benzoquinoline N-oxide

: 85-02-9
benzo[f]quinoline

Conditions

Conditions	Yield
With Methyl phenyldiazoacetate; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 60℃; for 12h; Inert atmosphere; Sealed tube; Molecular sieve;	92%

: 1086561-19-4
2-(2-methyl-pyridin-3-yl)-benzaldehyde

: 85-02-9
benzo[f]quinoline

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;	80%

: 91-59-8
naphthalen-2-ylamine

: 504-63-2
trimethyleneglycol

: 85-02-9
benzo[f]quinoline

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; oxygen; palladium diacetate; trifluoroacetic acid at 150℃; for 16h; Schlenk technique;	80%

: 17104-69-7
5,6-benzoquinoline N-oxide

A: 85-02-9
benzo[f]quinoline

B: 23981-08-0
benzoquinolin-1(2H)-one

C: 75539-85-4
2,3-dihydro-1H-benzindole-3-carbaldehyde

Conditions

Conditions	Yield
In water at 16℃; Irradiation;	A 3% B 74% C 4%

...Expand

: di-tert-butyl 1-cyclopropyl-2-(naphthalen-2-yl)hydrazine-1,2-dicarboxylate

: 85-02-9
benzo[f]quinoline

Conditions

Conditions	Yield
With phosphoric acid In water; 1,2-dichloro-benzene at 170℃; under 760.051 Torr; for 24h;	74%

: 17104-69-7
5,6-benzoquinoline N-oxide

A: 85-02-9
benzo[f]quinoline

B: 75539-85-4
2,3-dihydro-1H-benzindole-3-carbaldehyde

Conditions

Conditions	Yield
In cyclohexane at 16℃; Irradiation;	A 9% B 66%

: 20191-75-7
1-bromo-2-naphthylamine

: 56-81-5
glycerol

: 85-02-9
benzo[f]quinoline

Conditions

Conditions	Yield
With sulfuric acid at 150℃;

: 831-91-4
Benzyl phenyl sulfide

: 72490-90-5
benzoquinoline radical ion

A: 85-02-9
benzo[f]quinoline

B: 2154-56-5
benzyl radical

C: 13133-62-5
thiophenolate

Conditions

Conditions	Yield
With tetrabutylammonium perchlorate In N,N-dimethyl-formamide at 25℃; Rate constant; Thermodynamic data; ΔG0, cyclovoltammetry;

...Expand

polystyrene: polystyrene

A: 229-87-8
phenanthridine

B: 85-02-9
benzo[f]quinoline

C: 84-15-1
o-terphenyl

D: 20279-21-4
1,2,3,10b-tetrahydrofluoranthene

Conditions

Conditions	Yield
With air at 900℃; Condensation; combustion; pyrolysis; PAH formation; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts;	A 0.04 mg B 0.12 mg C 0.19 mg D 0.16 mg

...Expand

: 538-49-8
2-[(E)-2-phenylethenyl]pyridine

A: 85-02-9
benzo[f]quinoline

B: 538-49-8, 714-08-9, 1519-59-1
(Z)-2-(2-phenylethenyl)pyridine

C: 83023-13-6
rac-2,2'-((1R,2R,3S,4S)-2,4-diphenylcyclobutane-1,3-diyl)dipyridine

Conditions

Conditions	Yield
With cyclomaltooctaose Product distribution; Further Variations:; Reagents; Solvents; Dimerization; Isomerization, Aromatization; Irradiation;

...Expand

5.6-benzo-quinoline-carboxylic acid-(2): 5.6-benzo-quinoline-carboxylic acid-(2)

: 85-02-9
benzo[f]quinoline

Conditions

Conditions	Yield
at 190 - 200℃;

5.6-benzo-quinoline-dicarboxylic acid-(2.4): 5.6-benzo-quinoline-dicarboxylic acid-(2.4)

: 85-02-9
benzo[f]quinoline

5.6-tetramethylene-quinoline: 5.6-tetramethylene-quinoline

: 85-02-9
benzo[f]quinoline

Conditions

Conditions	Yield
ueber Bleioxyd-Bimsstein im Kohlendioxydstrom bei 700grad.;

: 80028-83-7
7,8,9,10-tetrahydrobenzoquinoline

lead oxide pumice stone: lead oxide pumice stone

: 85-02-9
benzo[f]quinoline

Conditions

Conditions	Yield
at 700℃;

: 7647-01-0
hydrogenchloride

: 66405-01-4
1,2,3,4-tetrahydrobenzo[f]quinolin-2-ol

: 7732-18-5
water

A: 85-02-9
benzo[f]quinoline

B: 40174-35-4
1,2,3,4-tetrahydro-5,6-benzoquinoline

Conditions

Conditions	Yield
at 200 - 210℃;

...Expand

: 7647-01-0
hydrogenchloride

: 2-(4-isobutyryl-3,4-dihydro-benzo[f]quinolin-3-yl)-2-methyl-propionic acid

A: 85-02-9
benzo[f]quinoline

B: 79-31-2
isobutyric Acid

...Expand

: 7664-93-9
sulfuric acid

: 7778-39-4, 121471-47-4
orthoarsenic acid

: 91-59-8
naphthalen-2-ylamine

: 56-81-5
glycerol

: 85-02-9
benzo[f]quinoline

...Expand

: 7664-93-9
sulfuric acid

: 98-95-3
nitrobenzene

: 91-59-8
naphthalen-2-ylamine

: 56-81-5
glycerol

: 85-02-9
benzo[f]quinoline

...Expand

: 7647-01-0
hydrogenchloride

: 581-89-5
2-nitronaphthalene

: 56-81-5
glycerol

: 85-02-9
benzo[f]quinoline

Conditions

Conditions	Yield
at 160 - 170℃;

...Expand

: 91-59-8
naphthalen-2-ylamine

oleum: oleum

: 85-02-9
benzo[f]quinoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / 1N HCl / 0.25 h / 40 °C 2: 56 percent / PPA / 2 h / 100 °C / other nitrogen containing heterocyclic compounds; var. reagents, var. temperatures and reaction time View Scheme

: 85-02-9
benzo[f]quinoline

: 75-24-1
trimethylaluminum

: 40961-80-6
trimethyl(5,6-benzoquinoline) aluminium(III)

Conditions

Conditions	Yield
In diethyl ether (N2); stirring (5 h, room temp.); evapn. (vac.), washing (Et2O), recrystn. (cyclohexane/benzene, 5/2); elem. anal.;	95%
In diethyl ether N2-atmosphere; molar ratio C13H9N/AlMe3 = 1:1.2, reacting for 5 h at room temp.; recrystn. from Et2O;

: 85-02-9
benzo[f]quinoline

: 1078-58-6
diphenylzinc

: 4067-83-8
3-phenylbenzo[f]quinoline

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); tricyclohexylphosphine In toluene at 100℃; for 20h; Inert atmosphere;	95%

: 85-02-9
benzo[f]quinoline

: 3155-30-4
4-(N,N-dimethylamino)benzaldehyde 4-nitrophenylhydrazone

: 115095-28-8
15-(4-Dimethylamino-phenyl)-17-(4-nitro-phenyl)-17H-16,17-diaza-14-azonia-cyclopenta[a]phenanthrene; perchlorate

Conditions

Conditions	Yield
With tetraethylammonium perchlorate In acetonitrile electrochemical oxidation;	94%

: 85-02-9
benzo[f]quinoline

: 108-86-1
bromobenzene

: 23827-05-6
5-phenylbenzo[f]quinoline

Conditions

Conditions	Yield
With dirhodium tetraacetate; 1,3-bis(mesityl)imidazolium chloride; sodium t-butanolate In toluene at 95℃; for 24h; regioselective reaction;	94%

: 85-02-9
benzo[f]quinoline

: 40174-35-4
1,2,3,4-tetrahydro-5,6-benzoquinoline

Conditions

Conditions	Yield
With hydrogen; dicarbonyldichlorobis(triphenylphosphine)ruthenium(II) In tetrahydrofuran at 180℃; for 2h; Product distribution; other reagents, catalysts, temperature, time;	92%
With cobalt(II) tetrafluoroborate hexahydrate; tris(2-diphenylphosphinophenyl)phosphine; hydrogen In tetrahydrofuran at 120℃; under 7500.75 Torr; for 15h; Autoclave; chemoselective reaction;	89%
With ammonium formate; palladium on activated charcoal In methanol for 1.5h; Heating;	57%

: 85-02-9
benzo[f]quinoline

: 70880-19-2
3‐chlorobenzo[f]quinoline

Conditions

Conditions	Yield
Stage #1: benzo[f]quinoline With n-butyllithium; 2-(N,N-dimethylamino)ethanol In hexane; toluene at -78℃; Stage #2: With hexachloroethane In hexane; toluene at -78 - 0℃; for 1.5h; Stage #3: With water In hexane; toluene at 0℃;	92%
Multi-step reaction with 2 steps 1: diethyl ether / Behandeln des Reaktionsprodukts mit wss.Ammoniak. 2: phosphoryl chloride View Scheme
Multi-step reaction with 2 steps 1: 150 °C / Behandeln des Reaktionsprodukts mit Kalium-hexacyanoferrat(III) und wss.Kalilauge 2: phosphorus (V)-chloride; phosphoryl chloride / 160 °C View Scheme

: 85-02-9
benzo[f]quinoline

: 591-51-5
phenyllithium

: 4067-83-8
3-phenylbenzo[f]quinoline

Conditions

Conditions	Yield
Stage #1: benzo[f]quinoline; phenyllithium With 1,2-dimethoxyethane In diethyl ether; hexane at 20℃; Stage #2: With water In diethyl ether; hexane	91%

: 85-02-9
benzo[f]quinoline

: 5469-26-1
1-Bromopinacolon

: 1-(3,3-dimethyl-2-oxobutyl)benzo[f]quinolin-1-ium bromide

Conditions

Conditions	Yield
In acetone at 20℃; for 28h; Reflux;	89%

: 85-02-9
benzo[f]quinoline

: 403-29-2
2-bromo-4'-fluoroacetophenone

: 1-(4-fluorophenacyl)benzo[f]quinolin-1-ium bromide

Conditions

Conditions	Yield
In acetone at 20℃; for 28h; Reflux;	87%

: 85-02-9
benzo[f]quinoline

: 1515876-36-4
3-[4-(2-bromoacetyl)phenyl]-2H-chromen-2-one

: 1515876-41-1
4-{2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl}benzo[f]quinolinium bromide

Conditions

Conditions	Yield
In toluene Reflux;	86%

: 85-02-9
benzo[f]quinoline

: 542-91-6
H2SiEt2

: 2-(diethylsilyl)-1,2,3,4-tetrahydrobenzo[f]quinoline

Conditions

Conditions	Yield
With tris(pentafluorophenyl)borate In chloroform at 20 - 65℃; for 6h; Inert atmosphere; stereoselective reaction;	85%

: 85-02-9
benzo[f]quinoline

: 20099-89-2
4-Cyanophenacyl bromide

: 1-(4-cyanophenacyl)benzo[f]quinolin-1-ium bromide

Conditions

Conditions	Yield
In acetone at 20℃; for 28h; Reflux;	85%

: 85-02-9
benzo[f]quinoline

: 3385-78-2
trimethyl indium

: 169897-52-3
trimethyl(5,6-benzoquinoline) indium(III)

Conditions

Conditions	Yield
In diethyl ether (N2); stirring; elem. anal.;	84%

: 85-02-9
benzo[f]quinoline

: 109-72-8, 29786-93-4
n-butyllithium

: 853924-15-9
3-butyl-benzo[f]quinoline

Conditions

Conditions	Yield
Stage #1: benzo[f]quinoline; n-butyllithium With 1,2-dimethoxyethane In diethyl ether; hexane at 20℃; Stage #2: With water In diethyl ether; hexane	84%

: 85-02-9
benzo[f]quinoline

: 144-48-9
iodacetamide

: 1-(2-amino-2-oxoethyl)benzo[f]quinolin-1-ium iodide

Conditions

Conditions	Yield
In acetone at 20℃; for 28h; Reflux;	84%

: 85-02-9
benzo[f]quinoline

: benzo[f]quinoline-d9

Conditions

Conditions	Yield
With deuteriated sodium hydroxide; water-d2 at 420 - 430℃; for 24h; supercritical pressure;	82%

: 85-02-9
benzo[f]quinoline

: 5202-78-8
acetylaminoethylene

: 96-32-2
bromoacetic acid methyl ester

: methyl (S)-4-acetamido-4-(benzo[f]quinolin-3-yl)butanoate

Conditions

Conditions	Yield
With potassium phosphate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; water In toluene at 25℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; enantioselective reaction;	81%

...Expand

: 85-02-9
benzo[f]quinoline

: 135-73-9
2-Bromo-4'-phenylacetophenone

: 1-(4-phenylphenacyl)benzo[f]quinolin-1-ium bromide

Conditions

Conditions	Yield
In acetone at 20℃; for 28h; Reflux;	80%

: 85-02-9
benzo[f]quinoline

: 99-73-0
para-bromophenacyl bromide

: 1-(4-bromophenacyl)benzo[f]quinolin-1-ium bromide

Conditions

Conditions	Yield
In acetone at 20℃; for 28h; Reflux;	80%

: 85-02-9
benzo[f]quinoline

: <5-(bromoacetyl)furfuryl>triphenylphosphonium bromide

: 2-(benzoquinolinioacetyl)-5-<(triphenylphosphonio)methyl>furan dibromide

Conditions

Conditions	Yield
In ethanol for 3h; Heating;	79%

: 85-02-9
benzo[f]quinoline

: 536-38-9
4-chlorobenzoylmethyl bromide

: 1-(4-chlorophenacyl)benzo[f]quinolin-1-ium bromide

Conditions

Conditions	Yield
In acetone at 20℃; for 28h; Reflux;	79%

: 85-02-9
benzo[f]quinoline

: 1445-79-0
trimethyl gallium

: 169897-51-2
trimethyl(5,6-benzoquinoline) gallium(III)

Conditions

Conditions	Yield
In diethyl ether (N2); stirring (5 h, room temp.); evapn. (vac.), washing (Et2O), recrystn. (cyclohexane); elem. anal.;	78%

: 85-02-9
benzo[f]quinoline

: 141556-45-8
1,3-bis(mesityl)imidazolium chloride

: 3-(3,5-dimethylphenyl)benzo[f]quinoline

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium t-butanolate In 1,3,5-trimethyl-benzene at 180℃; for 18h; Glovebox; Inert atmosphere; Sealed tube;	78%

: 85-02-9
benzo[f]quinoline

: 1184-58-3
dimethylaluminum chloride

: 40961-83-9
chlorodimethyl(5,6-benzoquinoline) aluminium(III)

Conditions

Conditions	Yield
In diethyl ether (N2); stirring; recrystn. (benzene); elem. anal.;	76%

: 85-02-9
benzo[f]quinoline

: 882-33-7
diphenyldisulfane

: 1222964-28-4
3-phenylthio-benzo[f]quinoline

Conditions

Conditions	Yield
Stage #1: benzo[f]quinoline With n-butyllithium; 2-(N,N-dimethylamino)ethanol In hexane; toluene at -78℃; Stage #2: diphenyldisulfane In hexane; toluene at -78 - 0℃; for 1.5h; Stage #3: With water In hexane; toluene at 0℃;	74%

: 85-02-9
benzo[f]quinoline

: 4-[4-(2-bromoacetyl)phenyl]-3-hydroxy-2H-chromen-2-one

: 1-{2-[4-(3-hydroxy-2-oxo-2H-chromen-4-yl)phenyl]-2-oxoethyl}benzo[f]quinolinium bromide

Conditions

Conditions	Yield
In toluene Reflux;	74%

Benzo[f]quinoline Chemical Properties

IUPAC Name: Benzo[f]quinoline
Synonyms: beta-Naphthoquinoline ; Benzo[f]quinoline ; b-Naphthoquinoline ; Naphthopyridine ; 1-Azaphenanthrene ; 5,6-Benzo(f)quinoline ; 5,6-benzoquinoline
CAS NO: 85-02-9
Molecular Formula of Benzo[f]quinoline (CAS NO.85-02-9) : C₁₃H₉N
Molecular Weight of Benzo[f]quinoline (CAS NO.85-02-9) : 179.22
Molecular Structure of Benzo[f]quinoline (CAS NO.85-02-9) :
EINECS: 201-582-0
Mol File: 85-02-9.mol
Merck : 1105
Index of Refraction: 1.726
Surface Tension: 54 dyne/cm
Density: 1.187 g/cm3
Flash Point: 155.9 °C
Enthalpy of Vaporization: 57.15 kJ/mol
Boiling Point: 350.4 °C at 760 mmHg
Vapour Pressure: 8.89E-05 mmHg at 25°C
Melting point: 89-91 °C
Appearance:Yellow crystals or white powder

Benzo[f]quinoline Uses

Benzo[f]quinoline (CAS NO.85-02-9) is use as raw materials of organic synthesis .

Benzo[f]quinoline Toxicity Data With Reference

1.		mma-sat 50 µg/plate		50NNAZ Polynuclear Aromatic Hydrocarbons: Mechanisms, Methods and Metabolism, Papers of the 8th International Symposium, Columbus, OH, 1983. 7 (1983),73.
2.		pic-esc 7500 ng/well		MUREAV Mutation Research. 260 (1991),349.

Benzo[f]quinoline Consensus Reports

EPA Genetic Toxicology Program.

Benzo[f]quinoline Safety Profile

Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes Harmful Xn
Risk Statements 40-36/37/38
S40:To clean the floor and all objects contaminated by this material, use .... (there follows suitable cleaning material).
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 45-36/37/39-26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RTECS DK1428000

Benzo[f]quinoline Specification

1.General Description :Yellow crystals or white powder. Characteristic irritating odor.
2.Air & Water Reactions: Sensitive to prolonged exposure to air. Insoluble in water.
Reactivity Profile : 5,6-Benzoquinoline neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.
3.Fire Hazard : 5,6-Benzoquinoline is combustible.

Product Name

5,6-BENZOQUINOLINE

Synthetic route

Benzo[f]quinoline Chemical Properties

Benzo[f]quinoline Uses

Benzo[f]quinoline Toxicity Data With Reference

Benzo[f]quinoline Consensus Reports

Benzo[f]quinoline Safety Profile

Benzo[f]quinoline Specification

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