607-35-2

Basic information

• Product Name: 8-Nitroquinoline
• Synonyms: 8-nitro-quinolin;Quinoline, 8-nitro-;Quinoline,8-nitro-;AKOS 214-03;8-NITROQUINOLINE;8-Nitroqunioline;8-Nitroquinoline,98%;8-Nitrochinolin
• CAS NO: 607-35-2
• Molecular Formula: C₉H₆N₂O₂
• Molecular Weight: 174.16
• EINECS: 210-135-9
• Product Categories: Quinolines, Quinazolines and derivatives;Quinoline&Isoquinoline;Quinolines;Nitroquinolines;Building Blocks;Heterocyclic Building Blocks
• Mol File: 607-35-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 89-91 °C(lit.)
• Boiling Point: 305.12°C (rough estimate)
• Flash Point: 149.2 °C
• Appearance: white to light yellow crystal powder
• Density: 1.2190 (estimate)
• Vapor Pressure: 0.000505mmHg at 25°C
• Refractive Index: 1.6820 (rough estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.20±0.17(Predicted)
• Water Solubility: Soluble in ethanol, ethyl ether and benzene, slightly soluble in cold water.
• BRN: 135178
• CAS DataBase Reference: 8-Nitroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Nitroquinoline(607-35-2)
• EPA Substance Registry System: 8-Nitroquinoline(607-35-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-40-68
• Safety Statements: 26-27-36/37/39-36
• WGK Germany: 3
• RTECS: VC1925000
• TSCA: Yes
• Hazardous Substances Data: 607-35-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

8-Nitroquinoline was used to prepare furazano [3,4-h] quinoline. It was also used to synthesize corresponding 2-substituted phenoxy-6-methoxy-8-aminoquinoline.

Safety Profile

Poison by intraperitoneal route. Experimental reproductive effects. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C9H6N2O2/c12-11(13)8-5-1-3-7-4-2-6-10-9(7)8/h1-6H

Synthetic route

8-quinolinylboronic acid (86-58-8) → 8-nitroquinoline (607-35-2)

Conditions	Yield
With N-Bromosuccinimide; [bis(trifluoroacetoxy)iodo]benzene; sodium nitrite In acetonitrile at 20℃; for 3h; regioselective reaction;	84%

2-nitro-aniline (88-74-4) + glycerol (56-81-5) → 8-nitroquinoline (607-35-2)

Conditions	Yield
Stage #1: 2-nitro-aniline; glycerol With sodium iodide at 20℃; for 0.0833333h; Stage #2: With sulfuric acid for 0.166667h; Cooling with ice; Stage #3: at 140℃; for 2h;	81%
Stage #1: 2-nitro-aniline With sulfuric acid at 70 - 80℃; Stage #2: glycerol at 70 - 80℃; Temperature; Further stages;	79%
With sulfuric acid In water for 4h; Reflux;	72%

8-nitro-1,2,3,4-tetrahydroquinoline (39217-93-1) → 8-nitroquinoline (607-35-2)

Conditions	Yield
With iodine; oxygen In 1,2-dichloro-benzene; toluene at 160℃; for 30h;	77%

2-nitro-aniline (88-74-4) + sodium 3-nitrobenzenesulfonate (127-68-4) → 8-nitroquinoline (607-35-2)

Conditions	Yield
With sulfuric acid In water; glycerol Reflux;	44%

quinoline (91-22-5) → 8-nitroquinoline (607-35-2) + 5-nitroquinoline (607-34-1)

Conditions	Yield
Stage #1: quinoline With sulfuric acid; nitric acid at 20℃; for 1h; Stage #2: With sodium carbonate In water	A 34% B 38%
With sulfuric acid; nitric acid In water at 0 - 20℃; for 1h;	A 35% B n/a
With sulfuric acid; nitric acid

quinoline (91-22-5) → 8-nitroquinoline (607-35-2)

Conditions	Yield
durch Nitrieren;

2-methoxy-3-nitro-cinnamaldehyde → 8-nitroquinoline (607-35-2)

Conditions	Yield
With ammonia at 130 - 140℃; im Rohr;

1-methyl-8-nitro-quinolinium; iodide (51741-75-4) → 8-nitroquinoline (607-35-2) + methyl iodide (74-88-4)

2-nitro-aniline (88-74-4) + acrolein (107-02-8) → 8-nitroquinoline (607-35-2)

Conditions	Yield
With phosphoric acid; water; orthoarsenic acid
With hydrogenchloride; phosphoric acid In water at 80 - 95℃; for 7h;

8-quinolinesulfonic acid (85-48-3) → 8-nitroquinoline (607-35-2)

Conditions	Yield
With nitric acid at 160℃; im Rohr;

8-nitro-quinoline-carboxylic acid-(2) → 8-nitroquinoline (607-35-2)

Conditions	Yield
durch Erhitzen ueber den Schmelzpunkt;

nitric acid (7697-37-2) + 8-quinolinesulfonic acid (85-48-3) → 8-nitroquinoline (607-35-2)

Conditions	Yield
at 160℃;

quinoline (91-22-5) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2) → 8-nitroquinoline (607-35-2) + 5-nitroquinoline (607-34-1)

Conditions	Yield
unter Kuehlung;
at 0℃;

quinoline (91-22-5) + nitric acid (7697-37-2) + acetic anhydride (108-24-7) → 8-nitroquinoline (607-35-2) + 3-nitroquinoline (17576-53-3) + 6-nitroquinoline (613-50-3)

quinoline (91-22-5) + acetic anhydride (108-24-7) + lithium nitrate + copper (I)-nitrate → 8-nitroquinoline (607-35-2) + 3-nitroquinoline (17576-53-3) + 6-nitroquinoline (613-50-3)

quinoline (91-22-5) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2) → 8-nitroquinoline (607-35-2) + 5-nitroquinoline (607-34-1) + 6,8-dinitroquinoline (88609-20-5) + 5,7-dinitroquinoline (62163-05-7)

Conditions	Yield
in der Hitze;

quinoline (91-22-5) + sulfuric acid (7664-93-9) → 8-nitroquinoline (607-35-2) + 5-nitroquinoline (607-34-1) + x.x-dinitro-x-oxy-quinoline

Conditions	Yield
beim Eintragen des Chinolin-nitrats;

sulfuric acid (7664-93-9) + orthoarsenic acid (7778-39-4, 121471-47-4) + 2-nitro-aniline (88-74-4) + glycerol (56-81-5) → 8-nitroquinoline (607-35-2)

sulfuric acid (7664-93-9) + nitrobenzene (98-95-3) + 2-nitro-aniline (88-74-4) + glycerol (56-81-5) → 8-nitroquinoline (607-35-2)

2-methoxy-3-nitro-cinnamaldehyde + ammonia (7664-41-7) → 8-nitroquinoline (607-35-2)

Conditions	Yield
at 140℃; im geschlossenen Rohr;

acrylaldehyde diethyl acetal (3054-95-3) + 2-nitro-aniline (88-74-4) → 8-nitroquinoline (607-35-2)

Conditions	Yield
With Ni-modified Beta zeolite In neat (no solvent) for 0.0833333h; Microwave irradiation; Reflux; Green chemistry;	19.4 %Chromat.

8-nitroquinoline (607-35-2) → 8-amino quinoline (578-66-5)

Conditions	Yield
With graphitic carbon nitride; hydrazine hydrate In water at 70℃; for 24h; Irradiation; Sealed tube; Green chemistry; chemoselective reaction;	100%
With hydrogen In water at 60℃; under 760.051 Torr; for 3h; Green chemistry;	99%
With hydrogen In tetrahydrofuran; water at 120℃; under 22502.3 Torr; for 6h; Autoclave;	99%

8-nitroquinoline (607-35-2) → 8-nitro-3-bromoquinoline (5341-07-1)

Conditions	Yield
With N-Bromosuccinimide In acetic acid for 2h;	100%
With N-Bromosuccinimide In acetic acid at 110℃; for 3h;	81.4%
With N-Bromosuccinimide In acetic acid at 65 - 70℃; for 6h; Inert atmosphere;	75%

8-nitroquinoline (607-35-2) → N-(quinolin-8-yl)hydroxylamine (57743-06-3)

Conditions	Yield
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;	99%
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; Inert atmosphere;	99%
With ethyl acetate; platinum Hydrogenation;

8-nitroquinoline (607-35-2) → 3,6-dibromo-8-nitroquinoline (158117-55-6)

Conditions	Yield
With N-Bromosuccinimide In acetic acid for 336h; Ambient temperature;	99%

8-nitroquinoline (607-35-2) → 3-iodo-8-nitroquinoline (497084-46-5)

Conditions	Yield
With N-iodo-succinimide; acetic acid at 100℃; for 3h;	99%
With N-iodo-succinimide; acetic acid at 62℃; for 22h;	97%
With N-iodo-succinimide In acetic acid at 62℃; for 22.1667h;	97%

8-nitroquinoline (607-35-2) → 3-chloro-8-nitroquinoline (73868-16-3)

Conditions	Yield
With N-chloro-succinimide In acetic acid for 2h;	96%
With N-chloro-succinimide; acetic acid for 3.5h; Heating;	34%
With N-chloro-succinimide; acetic acid at 110℃; for 1h; Inert atmosphere;	30%
With sulfur dichloride

8-nitroquinoline (607-35-2) + methyl trifluoromethanesulfonate (333-27-7) → 1-methyl-8-nitroquinolin-1-ium trifluoromethanesulfonate

Conditions	Yield
In benzene for 5h; Reflux;	95%
In dichloromethane at 0 - 35℃; Inert atmosphere;	69%

8-nitroquinoline (607-35-2) + 1-chloro-N,N-dimethylmethane sulfonamide (35427-68-0) → N,N-dimethyl-(8-nitro-7-quinolyl)methanesulfonamide (105199-32-4)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 0.5h;	92%

8-nitroquinoline (607-35-2) + 4-Phenylbenzaldehyde (3218-36-8) → C22H18N2

Conditions	Yield
With formic acid; triethylamine In water; tert-butyl alcohol at 100℃; for 24h;	91%

8-nitroquinoline (607-35-2) + benzene (71-43-2) → 4-phenyl-8-nitroquinoline (25771-65-7)

Conditions	Yield
Stage #1: 8-nitroquinoline With sulfuric acid at 35℃; for 0.416667h; Stage #2: benzene at 65℃; for 0.616667h; Temperature;	90%

8-nitroquinoline (607-35-2) + 2-Trifluoromethylbenzaldehyde (447-61-0) → N-(2-(trifluoromethyl)benzyl)quinolin-8-amine

Conditions	Yield
With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 80℃; for 24h;	90%
With tetrahydroxydiboron; copper diacetate In acetonitrile at 80℃; for 24h; Schlenk technique; chemoselective reaction;	68%

8-nitroquinoline (607-35-2) + diphenyliodonium tetrafluoroborate → 8-nitro-3-phenylquinoline (190137-72-5)

Conditions	Yield
With palladium; copper diacetate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; regioselective reaction;	89%

8-nitroquinoline (607-35-2) + p-methoxyphenyl(phenyl)iodonium tetrafluoroborate (733-53-9) → 3-(4-methoxyphenyl)-8-nitroquinoline

Conditions	Yield
With palladium; copper diacetate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; regioselective reaction;	89%

8-nitroquinoline (607-35-2) + 1-chloro-N,N-dimethylmethane sulfonamide (35427-68-0) → 5-(Dimethylaminosulfonylmethyl)-8-nitroquinoline (105199-33-5) + N,N-dimethyl-(8-nitro-7-quinolyl)methanesulfonamide (105199-32-4)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -30 - -25℃; for 0.25h;	A 4% B 88%

4-Trifluoromethylbenzaldehyde (455-19-6) + 8-nitroquinoline (607-35-2) → N-(4-(trifluoromethyl)benzyl)quinolin-8-amine

Conditions	Yield
With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 80℃; for 24h;	88%
With tetrahydroxydiboron; copper diacetate In acetonitrile at 80℃; for 24h; Schlenk technique; chemoselective reaction;	70%

8-nitroquinoline (607-35-2) → 5-amino-8-nitroquinoline (42606-39-3)

Conditions	Yield
With hydroxylamine hydrochloride; potassium hydroxide In ethanol at 40 - 60℃; for 2.5h;	87%
With potassium hydroxide; hydroxylamine hydrochloride In ethanol at 20℃; for 1h;	55%
With hydrogenchloride; potassium hydroxide; ethanol; hydroxylamine

8-nitroquinoline (607-35-2) + 2-Fluorobenzaldehyde (446-52-6) → N-(2-fluorobenzyl)quinolin-8-amine

Conditions	Yield
With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 80℃; for 24h;	87%
With tetrahydroxydiboron; copper diacetate In acetonitrile at 80℃; for 24h; Schlenk technique; chemoselective reaction;	66%

8-nitroquinoline (607-35-2) + benzaldehyde (100-52-7) → N-(quinolin-8-yl)benzylamine (37385-01-6)

Conditions	Yield
With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 80℃; for 24h;	86%
With tetrahydroxydiboron; copper diacetate In acetonitrile at 80℃; for 24h; Schlenk technique; chemoselective reaction;	82%
With hydrogen In tetrahydrofuran; water at 110℃; under 37503.8 Torr; for 24h; Autoclave;	79 %Chromat.

8-nitroquinoline (607-35-2) + (4-chlorophenyl)phenyliodonium tetrafluoroborate → 3-(4-chlorophenyl)-8-nitroquinoline

Conditions	Yield
With palladium; copper diacetate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere; regioselective reaction;	86%

8-nitroquinoline (607-35-2) + chloromethyl phenyl sulfone (7205-98-3) → 8-Nitro-7-(phenylsulfonylmethyl)quinoline (105199-29-9) + 8-Nitro-5-(phenylsulfonylmethyl)quinoline (105199-30-2)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 0.5h;	A 84% B 12%

8-nitroquinoline (607-35-2) → 8-nitro-1,2,3,4-tetrahydroquinoline (39217-93-1)

Conditions	Yield
With iodine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 20℃; Inert atmosphere;	84%
With iron(II) triflate; C13H21N3O2 In chloroform at 40℃; for 4h; Schlenk technique;	76%
With ammonia borane; C52H64N12Pd2S4(2+)*2F6P(1-) In dodecane; toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;	58 %Chromat.

8-nitroquinoline (607-35-2) + 4-nitrobenzamide (619-80-7) → 4-nitro-N-(8-nitroquinolin-5-yl)benzamide

Conditions	Yield
With sodium hydride; dimethyl sulfoxide; potassium hexacyanoferrate(III) In paraffin oil at 20℃; for 6h;	84%

8-nitroquinoline (607-35-2) + chloromethyl phenyl sulfone (7205-98-3) → 8-Nitro-7-(phenylsulfonylmethyl)quinoline (105199-29-9)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -30 - -25℃; for 0.25h;	83%

8-nitroquinoline (607-35-2) + dimethyl amine (124-40-3) + Dimethyl phosphite (868-85-9) → dimethyl (9-aza-1-(dimethylamino)-5H-2-benzazepin-3-yl)phosphonate (131214-36-3)

Conditions	Yield
With sodium methylate In methanol at 5 - 10℃;	81%

8-nitroquinoline (607-35-2) → 8-amino-1,2,3,4-tetrahydroquinoline (54012-92-9)

Conditions	Yield
With hexarhodium hexadecacarbonyl; carbon monoxide; water In 2-methoxy-ethanol at 150℃; under 41188.4 Torr; for 48h;	81%
With carbon monoxide; water In 2-methoxy-ethanol at 150℃; under 41188.4 Torr; for 48h;	81%
With hydrogen; acetic acid; platinum(IV) oxide at 20℃; under 1034.32 Torr; for 20h;	79%

8-nitroquinoline (607-35-2) + [2-(acetoxymethyl)prop-2-enyl]trimethylsilane (72047-94-0) → 8-methylene-9a-nitro-7,8,9,9a-tetrahydro-6aH-cyclopenta[h]quinoline

Conditions	Yield
Stage #1: 8-nitroquinoline With N,N-bis(-1-phenylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine; bis(dibenzylideneacetone)-palladium(0) In toluene at 25℃; for 0.0833333h; Inert atmosphere; Sealed tube; Stage #2: [2-(acetoxymethyl)prop-2-enyl]trimethylsilane In toluene at 25℃; for 15h; Inert atmosphere; Sealed tube;	81%

8-nitroquinoline (607-35-2) + (4-chlorophenoxy)acetonitrile (3598-13-8) → 2-(8-nitroquinolin-7-yl)acetonitrile (105214-06-0)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at -16 - 20℃; for 2h;	80%
With potassium tert-butylate In tetrahydrofuran at -10℃; for 0.416667h;	58%

8-nitroquinoline (607-35-2) + 2,5-hexanedione (110-13-4) → 8-(2,5-dimethyl-1H-pyrrol-1-yl)quinoline (32668-78-3)

Conditions	Yield
With indium; acetic acid In toluene at 80℃; for 24h; Inert atmosphere;	80%
With hydrogen In neat (no solvent) at 120℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; chemoselective reaction;	55%

Upstream product

• 88-74-4 2-nitro-aniline 
• 56-81-5 glycerol 
• 107-02-8 acrolein 
• 91-22-5 quinoline 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 7664-93-9 sulfuric acid 
• 7778-39-4 orthoarsenic acid 
• 98-95-3 nitrobenzene 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 39217-93-1 8-nitro-1,2,3,4-tetrahydroquinoline 
• 86-58-8 8-quinolinylboronic acid 
• 7664-41-7 ammonia 
• 85-48-3 8-quinolinesulfonic acid 

Downstream Products

• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 578-66-5 8-amino quinoline 
• 6338-98-3 7-chloro-[8]quinolylamine 
• 25369-31-7 7-nitroindoline-2-one 
• 716328-53-9 2-cyclohexyl-8-nitro-quinoline 
• 716328-57-3 2,4-dicyclohexyl-8-nitro-quinoline 
• 835898-99-2 5-hydroxy-6-p-tolylsulfonyl-8-p-tolylsulfonylaminoquinoline 
• 37385-01-6 N-(quinolin-8-yl)benzylamine 

Relevant articles and documents

Direct amination of nitroquinoline derivatives via nucleophilic displacement of aromatic hydrogen

The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one illustrate the nitro/nitroso conversion within VNS reaction. Additionally, 9-(8-isopropyl-2-((8-isopropyl-2-methyl5-nitroquinolin-6-yl)methyl)-5-nitrosoquinolin-6-yl)-9H-carbazole is presented as a double VNS product. It is postulated that the potassium counterion interacts with the oxygen on the nitro group, which could influence nucleophile attack in that way.

Iodine-catalyzed convergent aerobic dehydro-aromatization toward benzazoles and benzazines

An iodine-catalyzed aerobic dehydro-aromatization has been developed, providing straightforward and efficient access to various benzoazoles and benzoazines. The present transition-metal-free protocol enables the dehydro-aromatization of tetrahydrobenzazoles and tetrahydroquinolines with molecular oxygen as the green oxidant, along with some other N-heterocycles. Hence, a broad range of heteroaromatic compounds are generated in moderate to good yields under facile reaction conditions.

Synthetic method of 8-nitroquinoline

The invention provides a synthetic method of 8-nitroquinoline. The synthetic method comprises the following steps: taking ortho-nitroaniline and glycerinum as raw materials, carrying out dehydration in sulfuric acid, and taking iodine-potassium iodide as an oxidizing agent to cyclize 8-nitroquinoline. At the temperature of 60 to 120 DEG C, glycerinum is added dropwise, the dehydration reaction ofglycerinum and sulfuric acid is mild and controllable, and then the cyclization reaction with ortho-nitroaniline is mild and controllable quickly, so that heat release controllability of sharp reaction cannot be caused. An iodine-potassium iodide water solution is used for taking the place of diarsenic pentoxide as an oxidant, the synthetic method is safe and pollution-free, simple in operation and relatively high in yield. The iodine-potassium iodide catalyst is mild, when a back flow becomes clear from muddy, the reaction is basically finished, the phenomenon is obvious, the reaction endpoint is easy to control, gas phase tracking detection can be realized, the post-treatment is simple, little waste water is generated, and the production process is safe and environmentally-friendly.