Conditions | Yield |
---|---|
With Tris(3,6-dioxaheptyl)amine; sodium nitrite; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos In tert-butyl alcohol at 130℃; for 24h; Product distribution / selectivity; Inert atmosphere; | 97% |
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; tris(3,5-dioxaheptyl)amine; sodium nitrite In tert-butyl alcohol at 130℃; for 24h; regioselective reaction; | 97% |
quinolin-6-yl triflate
6-nitroquinoline
Conditions | Yield |
---|---|
With Tris(3,6-dioxaheptyl)amine; sodium nitrite; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos In tert-butyl alcohol at 130℃; for 24h; Product distribution / selectivity; Inert atmosphere; | 94% |
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; tris(3,5-dioxaheptyl)amine; sodium nitrite In tert-butyl alcohol at 130℃; for 24h; regioselective reaction; | 94% |
6-nitro-1,2,3,4-tetrahydroquinoline
6-nitroquinoline
Conditions | Yield |
---|---|
With perylene diimide covalent immobilized to SiO2 nanospheres; air In N,N-dimethyl acetamide at 20℃; UV-irradiation; | 91% |
With iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support In acetonitrile at 100℃; under 11251.1 Torr; for 24h; Autoclave; | 89% |
With hexagonal boron carbon nitride In water at 25℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; | 89% |
Conditions | Yield |
---|---|
With potassium nitrite; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 130℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction; | 82% |
With potassium nitrite; basolite C300 In dimethyl sulfoxide at 130℃; for 48h; Inert atmosphere; | 78% |
6-nitroquinoline-N-oxide
6-nitroquinoline
Conditions | Yield |
---|---|
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Irradiation; chemoselective reaction; | 73% |
4-nitro-N-2-propynylbenzenamine
6-nitroquinoline
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 70℃; for 72h; Sealed tube; | 57% |
Conditions | Yield |
---|---|
With arsenic(III) trioxide Skraup reaction; | 47% |
Conditions | Yield |
---|---|
With sulfuric acid; iodine at 160 - 170℃; for 2h; Cycloaddition; Aromatization; | 18.3% |
With sulfuric acid; nitrobenzene | |
With sulfuric acid; orthoarsenic acid | |
With sulfuric acid; vanadia; sodium 3-nitrobenzenesulfonate at 145℃; | |
With sulfuric acid In water at 36 - 200℃; for 0.25h; Microwave irradiation; Green chemistry; |
6-azidoquinoline
A
6-nitroquinoline
B
3-nitrosoindolizine-8-carbaldehyde
C
C18H12N4O4
Conditions | Yield |
---|---|
With oxygen In acetonitrile at 20℃; Irradiation; | A 14% B n/a C n/a |
With oxygen In acetonitrile at 19.84℃; Irradiation; | A 14% B n/a C n/a |
Conditions | Yield |
---|---|
With sulfuric acid; dihydrogen peroxide; acetic acid und Natriumnitrit; |
Conditions | Yield |
---|---|
With sulfuric acid; nitrobenzene |
Conditions | Yield |
---|---|
With arsenic(V) oxide; sulfuric acid |
6-nitroquinoline
Conditions | Yield |
---|---|
durch Sublimation; |
6-nitroquinoline
Conditions | Yield |
---|---|
With sulfuric acid; water; orthoarsenic acid |
quinoline
nitric acid
acetic anhydride
A
8-nitroquinoline
B
3-nitroquinoline
C
6-nitroquinoline
quinoline
acetic anhydride
A
8-nitroquinoline
B
3-nitroquinoline
C
6-nitroquinoline
sulfuric acid
nitrobenzene
4-nitro-aniline
glycerol
6-nitroquinoline
1-methanesulfonyl-6-nitro-1,2-dihydro-quinoline
6-nitroquinoline
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 80℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Et3N / methanol 2: 16 percent / TfOH / CH2Cl2 / 2 h / 0 °C 3: KOH / dimethylsulfoxide / 80 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine / CH2Cl2 / 20 °C 2: Et3N / methanol 3: 16 percent / TfOH / CH2Cl2 / 2 h / 0 °C 4: KOH / dimethylsulfoxide / 80 °C View Scheme |
N-(4-nitro-phenyl)-N-(3-oxo-propyl)-methanesulfonamide
6-nitroquinoline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 16 percent / TfOH / CH2Cl2 / 2 h / 0 °C 2: KOH / dimethylsulfoxide / 80 °C View Scheme |
Conditions | Yield |
---|---|
With water In 1,4-dioxane; water Kinetics; byproducts: H2; hydrolysis of the amine-borane in an aq. dioxane soln. at 25°C; |
Conditions | Yield |
---|---|
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h; | 100% |
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol at 20℃; for 2h; | 100% |
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; Microwave irradiation; Green chemistry; | 99% |
6-nitroquinoline
6-nitroquinoline-borane
Conditions | Yield |
---|---|
In tetrahydrofuran stirring a mixt. of 4-chloroquinoline and BF3*THF in dry THF at 0°C under N2; isolation of the amine-borane from the reaction mixt. by removal of thesolvent; | 100% |
6-nitroquinoline
5-amino-6-nitroquinoline
Conditions | Yield |
---|---|
With N,N-tetramethylene-thiocarbamoyl-sulphenamide | 98% |
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide at 20℃; for 1h; | 95% |
With hydroxylamine hydrochloride | 94% |
Conditions | Yield |
---|---|
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 4h; Inert atmosphere; chemoselective reaction; | 96% |
With cobalt nanoparticles coated by N,P-codoped carbon shell pyrolyzed at 800°C In tetrahydrofuran at 120℃; for 12h; Schlenk technique; Inert atmosphere; | 78% |
Conditions | Yield |
---|---|
Stage #1: tris-iso-propylsilyl acetylene With isopropylmagnesium bromide In tetrahydrofuran; 2-methyltetrahydrofuran for 1h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #3: 6-nitroquinoline; Allyl chloroformate Further stages; | 96% |
6-nitroquinoline
2-Diazo-3-oxo-butyric acid methyl ester
benzyl chloroformate
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate; triethylamine In dichloromethane at 5 - 8℃; for 1h; | 95% |
6-nitroquinoline
6-nitro-1,2,3,4-tetrahydroquinoline
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; water In water; isopropyl alcohol for 17h; Heating; | 94% |
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; C38H52N4Se2(2+)*2CF3O3S(1-) In chloroform-d1 at 20℃; for 12h; Sealed tube; | 92% |
With formic acid; sulfuric acid In water at 80℃; for 24h; pH=2.5; Schlenk technique; Inert atmosphere; | 91% |
6-nitroquinoline
6-nitroquinoline-N-oxide
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In chloroform | 93% |
With dihydrogen peroxide In water for 0.333333h; Sonication; | 88% |
With fluorosulfonyl fluoride; dihydrogen peroxide; potassium carbonate In methanol at 23 - 32℃; Sealed tube; | 84.9% |
6-nitroquinoline
1-chloro-N,N-dimethylmethane sulfonamide
5-(Dimethylaminosulfonylmethyl)-6-nitroquinoline
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -30 - -25℃; for 0.25h; | 92% |
Conditions | Yield |
---|---|
With silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 83℃; for 4h; | 92% |
6-nitroquinoline
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; iodine In water; acetonitrile at 80℃; for 17h; regioselective reaction; | 91% |
With tert.-butylhydroperoxide; iodine In 1,2-dichloro-ethane at 120℃; for 24h; regioselective reaction; | 69% |
Conditions | Yield |
---|---|
With formic acid for 12h; Autoclave; Inert atmosphere; Green chemistry; | A 8.3% B 90.6% |
6-nitroquinoline
1-Phenyl-2-(trimethylsilyl)acetylene
phenyl chloroformate
Conditions | Yield |
---|---|
With silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 83℃; for 4h; | 90% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 5℃; for 2h; | 90% |
6-nitroquinoline
6-nitro-1,2-dihydroquinolin-2-one
Conditions | Yield |
---|---|
With water; chloroacetic acid ethyl ester In ethyl acetate for 0.5h; Microwave irradiation; | 89% |
With xanthine oxidase from bovine milk; oxygen In aq. phosphate buffer; N,N-dimethyl-formamide at 40℃; for 72h; pH=7.4; Concentration; Reagent/catalyst; Enzymatic reaction; | 2% |
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / 20 °C 2: water; potassium carbonate; p-toluenesulfonyl chloride / chloroform / 20 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: 6-nitroquinoline With [2,2]bipyridinyl; [MoO2Cl2(dmf)2] In toluene for 0.0333333h; Stage #2: phenylboronic acid With triphenylphosphine In toluene at 100℃; for 14h; | 87% |
6-nitroquinoline
6-nitro-quinolin-5-ol
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; potassium tert-butylate In ammonia at -33℃; | 86% |
6-nitroquinoline
Conditions | Yield |
---|---|
With sulfuric acid; fluorine at 5℃; | 86% |
With FlutecTM PP11; sulfuric acid; fluorine at 15℃; |
6-nitroquinoline
3,4-(methylenedioxy)-benzeneboronic acid
Conditions | Yield |
---|---|
With sodium metabisulfite; lithium phosphate; choline chloride In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere; | 85% |
With sodium metabisulfite; lithium phosphate; choline chloride; water In N,N-dimethyl-formamide at 130℃; for 10h; Schlenk technique; Inert atmosphere; | 85% |
6-nitroquinoline
chloromethyl phenyl sulfone
6-Nitro-5-(phenylsulfonylmethyl)quinoline
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 0.5h; | 83% |
6-nitroquinoline
2-chloro-propionic acid methyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 5℃; for 2h; | 83% |
Conditions | Yield |
---|---|
In water at 20℃; for 5h; | 81% |
With zinc(II) acetate dihydrate; acetic acid; zinc In water at 20℃; for 5h; | 51% |
6-nitroquinoline
(4-chlorophenoxy)acetonitrile
(6-Nitro-5-quinolinyl)acetonitrile
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -10℃; for 0.416667h; | 80% |
6-nitroquinoline
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere; | 80% |
6-nitroquinoline
5-styryl-4-nitro-3-methylisoxazole
Conditions | Yield |
---|---|
In water at 120℃; for 15h; Inert atmosphere; Green chemistry; | 80% |
Conditions | Yield |
---|---|
In benzene for 0.5h; Reflux; | 80% |
IUPAC Name: 6-Nitroquinoline
Synonyms: 6-Nitroquinoline ; 6-Nitro-quinolin ; Quinoline,6-nitro- ; 6-Nitroquinoline98% ; 6-Nitrochinolin ; 6-Nitro Quinoline - 50g
Product Categories: Nitroquinolines;Quinolines;Building Blocks;Heterocyclic Building Blocks
Molecular Structure of 6-Nitroquinoline (CAS NO.613-50-3) :
Molecular Formula of 6-Nitroquinoline (CAS NO.613-50-3) : C9H6N2O2
Molecular Weight of 6-Nitroquinoline (CAS NO.613-50-3) : 174.16
CAS NO: 613-50-3
EINECS: 210-346-6
BRN : 136138
Index of Refraction: 1.682
Surface Tension: 61.8 dyne/cm
Density: 1.354 g/cm3
Flash Point: 156.7 °C
Enthalpy of Vaporization: 55.56 kJ/mol
Boiling Point: 335.4 °C at 760 mmHg
Vapour Pressure: 0.000233 mmHg at 25°C
Melting point 151-153 ºC
Appearance:beige to light brown powder
6-Nitroquinoline (CAS NO.613-50-3) is used in organic synthesis.
With P-Nitroaniline as raw materials, condensation with Acrolein, after cyclization,obtainedof 6-Nitroquinoline (CAS NO.613-50-3), or cyclization with the glycerol,obtained of 6-Nitroquinoline (CAS NO.613-50-3).
1. | mma-sat 100 µmol/plate | MUREAV Mutation Research. 58 (1978),11. | ||
2. | mmo-esc 5700 nmol/L | ENMUDM Environmental Mutagenesis. 3 (1981),11. |
Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also 2-NITROQUINOLINE; 5-NITROQUINOLINE; 8-NITROQUINOLINE; 4-NITROQUINOLINE-N-OXIDE.
Hazard Codes Xn
Risk Statements 20/21/22-40
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R40:Limited evidence of a carcinogenic effect.
Safety Statements 7-22-36-45
S7:Keep container tightly closed.
S22:Do not breathe dust.
S36:Wear suitable protective clothing.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany 3
RTECS VC1900000
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