723281-72-9

Basic information

• Product Name: 6-BROMO-4-CHLORO-3-NITROQUINOLINE
• Synonyms: 6-BROMO-4-CHLORO-3-NITROQUINOLINE;Quinoline, 6-broMo-4-chloro-3-nitro-
• CAS NO: 723281-72-9
• Molecular Formula: C₉H₄BrClN₂O₂
• Molecular Weight: 287.5
• Mol File: 723281-72-9.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 387.626 °C at 760 mmHg
• Flash Point: 188.23 °C
• Appearance: /
• Density: 1.834
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.711
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: -1.08±0.27(Predicted)
• CAS DataBase Reference: 6-BROMO-4-CHLORO-3-NITROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-4-CHLORO-3-NITROQUINOLINE(723281-72-9)
• EPA Substance Registry System: 6-BROMO-4-CHLORO-3-NITROQUINOLINE(723281-72-9)

Safety Data

• Hazardous Substances Data: 723281-72-9(Hazardous Substances Data)

Usage

General Description

6-Bromo-4-Chloro-3-Nitroquinoline is a chemical compound with a complex structure. It contains specific elements including bromine, chlorine, nitrogen, and oxygen attached to a quinoline structure. 6-BROMO-4-CHLORO-3-NITROQUINOLINE is known for its specific color and crystalline structure. Usually, it's synthesized under controlled conditions in the laboratory due to its specific arrangement of atoms. There's scarce data available on its potential uses, toxicity, or safety, and therefore should be handled with caution, in a professional and controlled environment. However, various compounds with similar quinoline structures are often used in the production of dyes, pharmaceuticals, and other valuable scientific applications.

InChI:InChI=1/C9H4BrClN2O2/c10-5-1-2-7-6(3-5)9(11)8(4-12-7)13(14)15/h1-4H

Synthetic route

6-bromo-3-nitroquinolin-4-ol (853908-50-6) → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
With trichlorophosphate for 0.75h; Reflux;	100%
With trichlorophosphate at 100℃; for 4h;	95%
With trichlorophosphate at 100℃; for 3h;	95%

C10H6BrNO3 → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
With trichlorophosphate at 120℃; for 1h;	53%

(E)-5-bromo-2-((2-nitrovinyl)amino)benzoic acid (1201643-75-5) → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium acetate / acetic anhydride / 3 h / 120 °C 2: trichlorophosphate / 0.75 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: potassium acetate; acetic anhydride / 2 h / 120 °C 2: trichlorophosphate; N,N-dimethyl-formamide / 4 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: acetic anhydride; potassium acetate / 2 h / 120 °C 2: trichlorophosphate / 4 h / 100 °C View Scheme

5-bromo-2-((2-nitroethenyl)amino)benzoic acid (853908-49-3) → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride; potassium acetate / 3 h / 120 °C 2: trichlorophosphate / 0.75 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: acetic anhydride; sodium acetate / 2 h / 120 °C 2: trichlorophosphate / 0.75 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium acetate; acetic anhydride / 1.5 h / 120 °C 2: trichlorophosphate / 0.75 h / 120 °C View Scheme

5-Bromo-2-aminobenzoic acid (5794-88-7) → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 24 h / 20 °C 2: 24 h / 20 °C 3: acetic anhydride; sodium acetate / 2 h / 120 °C 4: trichlorophosphate / 0.75 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 24 h / 20 °C 2: 24 h / 20 °C 3: acetic anhydride; potassium acetate / 2 h / 120 °C 4: trichlorophosphate / 0.75 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 24 h / 20 °C 2: 24 h / 20 °C 3: potassium acetate; acetic anhydride / 2 h / 120 °C 4: trichlorophosphate / 0.75 h / Reflux View Scheme

2-amino-5-bromobenzoic acid hydrochloride (74189-16-5) → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 24 h / 20 °C 2: acetic anhydride; sodium acetate / 2 h / 120 °C 3: trichlorophosphate / 0.75 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: 24 h / 20 °C 2: acetic anhydride; potassium acetate / 2 h / 120 °C 3: trichlorophosphate / 0.75 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: 24 h / 20 °C 2: potassium acetate; acetic anhydride / 2 h / 120 °C 3: trichlorophosphate / 0.75 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: 24 h / 20 °C 2: potassium acetate; acetic anhydride / 2 h / 120 °C 3: trichlorophosphate / 0.75 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 2.17 h / 0 - 20 °C 1.2: 0 °C 1.3: 18 h / 20 °C 2.1: potassium acetate; acetic anhydride / 1.5 h / 120 °C 3.1: trichlorophosphate / 0.75 h / 120 °C View Scheme

4-bromo-aniline (106-40-1) → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ethanol / 0.17 h / 90 °C 1.2: 0.5 h 2.1: diphenylether / 0.08 h / 220 °C 3.1: nitric acid / propionic acid / 2 h / 125 °C 4.1: trichlorophosphate; triethylamine / 1.5 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: ethanol / 6 h / 105 °C 2: diphenylether / 0.25 h / 200 °C / Microwave irradiation 3: nitric acid / propionic acid / 2 h / 125 °C 4: trichlorophosphate / N,N-dimethyl-formamide / 3 h / 100 °C View Scheme

C13H12BrNO4 (1551219-53-4) → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: diphenylether / 0.08 h / 220 °C 2: nitric acid / propionic acid / 2 h / 125 °C 3: trichlorophosphate; triethylamine / 1.5 h / Reflux View Scheme

6-bromoquinolin-4-ol (145369-94-4) → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / propionic acid / 2 h / 125 °C 2: trichlorophosphate; triethylamine / 1.5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: nitric acid / propionic acid / 2 h / 125 °C 2: trichlorophosphate / N,N-dimethyl-formamide / 3 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: nitric acid / propionic acid / 2 h / 125 °C 2: N,N-dimethyl-formamide; trichlorophosphate / 2 h / 110 °C View Scheme
Multi-step reaction with 2 steps 1: nitric acid; propionic acid / 2 h 2: trichlorophosphate / N,N-dimethyl-formamide / 110 °C View Scheme

anthranilic acid (118-92-3) → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: ammonium bromide; dihydrogen peroxide; acetic acid / 16 h / 10 - 20 °C 2: ethanol / 18 h / 20 °C 3: potassium acetate; acetic anhydride / 2 h / 120 °C 4: trichlorophosphate; N,N-dimethyl-formamide / 4 h / Reflux View Scheme

5-(((4-bromophenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (187278-01-9) → 6-bromo-4-chloro-3-nitroquinoline (723281-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: diphenylether / 0.25 h / 200 °C / Microwave irradiation 2: nitric acid / propionic acid / 2 h / 125 °C 3: trichlorophosphate / N,N-dimethyl-formamide / 3 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: 0.17 h / 200 °C / 7757.43 Torr / Microwave irradiation 2: nitric acid / propionic acid / 2 h / 125 °C 3: N,N-dimethyl-formamide; trichlorophosphate / 2 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: diphenylether / 0.25 h / 190 °C 2: nitric acid; propionic acid / 2 h 3: trichlorophosphate / N,N-dimethyl-formamide / 110 °C View Scheme

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + rac-3-aminocyclopentanol hydrochloride (1184919-69-4) → 3-(6-bromo-3-nitroquinolin-4-yl)aminocyclopentanol

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2.5h;	100%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + (R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester (147081-49-0) → tert-butyl (S)-3-((6-bromo-3-nitroquinolin-4-yl)amino)pyrrolidine-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	99.7%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + methyl 1-aminocyclopropane-1-carboxylate (72784-43-1) → methyl 1-((6-bromo-3-nitroquinolin-4-yl)amino)cyclopropane-1-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 60℃; for 1h;	99%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + (R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester (147081-49-0) → tert-butyl (R)-3-((6-bromo-3-nitroquinolin-4-yl)amino)pyrrolidine-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	96.7%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + tert-butyl (3S)-3-aminopiperidine-1-carboxylate (625471-18-3) → tert-butyl (S)-3-((6-bromo-3-nitroquinolin-4-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6h;	96%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + trans-N-Boc-1,4-cyclohexanediamine (177906-48-8) → tert-butyl N-{4-[(6-bromo-3-nitroquinolin-4-yl)amino]cyclohexyl}carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 20℃; for 2h;	95%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + C21H22N2O2 → C30H25BrN4O4

Conditions	Yield
With acetic acid at 20℃; for 2h;	93.75%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) → 6-bromo-3-nitroquinolin-4-amine (1449518-65-3)

Conditions	Yield
With ammonia In water; acetonitrile at 20 - 50℃; for 1h;	93%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + methylamine (74-89-5) → 6-bromo-N-methyl-3-nitroquinoline-4-amine

Conditions	Yield
In diethyl ether at 20℃; for 0.5h;	93%
With triethylamine at 26℃; for 12h;	4.2 g
With triethylamine In ethanol at 20 - 60℃;

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + 1-(tert-butoxycarbonyl)-4-aminopiperidine (87120-72-7) → tert-butyl 4-((6-bromo-3-nitroquinolin-4-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6h;	93%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;	55.1%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + 3-trifluoromethylaniline (98-16-8) → 6-bromo-3-nitro-N-(3-(trifluoromethyl)phenyl)quinolin-4-amine

Conditions	Yield
In 1,4-dioxane at 20 - 150℃; for 2h;	92%
In 1,4-dioxane at 150℃; for 0.166667h; Microwave irradiation;
In 1,4-dioxane at 150℃;

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + 3-amino-1-(t-butoxycarbonyl)pyrrolidine (186550-13-0) → tert-butyl 3-((6-bromo-3-nitroquinolin-4-yl)amino)pyrrolidine-1-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6h;	92%
With triethylamine In dichloromethane at 20℃;	85%

3-aminoazetidine-1-carboxylic acid tert-butyl ester (193269-78-2) + 6-bromo-4-chloro-3-nitroquinoline (723281-72-9) → tert-butyl 3-((6-bromo-3-nitroquinolin-4-yl)amino)azetidine-1-formate

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	91.09%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + 4-trifluoromethylphenylamine (455-14-1) → 6-bromo-3-nitro-N-(4-(trifluoromethyl)phenyl)quinolin-4-amine

Conditions	Yield
With sodium acetate; acetic acid at 20℃; for 0.5h;	91%
In 1,4-dioxane at 150℃; for 0.166667h; Microwave irradiation;

methyl (1s,4s)-4-amino-cyclohexanecarboxylate + 6-bromo-4-chloro-3-nitroquinoline (723281-72-9) → methyl (1s,4s)-4-((6-bromo-3-nitroquinolin-4-yl)amino)cyclohexanecarboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	91%

morpholine (110-91-8) + 6-bromo-4-chloro-3-nitroquinoline (723281-72-9) → 6-bromo-4-(morpholin-4-yl)-3-nitroquinoline

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 20℃; for 1.5h;	91%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + 2-(4-aminophenyl)-2-methylpropionitrile (115279-57-7) → 2-(4-((6-bromo-3-nitroquinolin-4-yl)amino)phenyl)-2-methylpropanenitrile (915019-51-1)

Conditions	Yield
With acetic acid at 20℃; for 2h;	90%
In acetic acid at 25℃; for 0.5h;	89%
With sodium acetate; acetic acid at 20℃; for 0.5h;	86%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + methyl 1-(4-amino-2-(trifluoromethyl)phenyl)piperidine-4-carboxylate (1223003-56-2) → methyl 1-(4-(6-bromo-3-nitroquinolin-4-ylamino)-2-(trifluoromethyl)phenyl)piperidine-4-carboxylate (1223003-41-5)

Conditions	Yield
In 1,4-dioxane at 20 - 85℃; Inert atmosphere;	90%

benzyl 4-(4-aminophenyl)piperazine-1-carboxylate (947673-12-3) + 6-bromo-4-chloro-3-nitroquinoline (723281-72-9) → C28H27N5O4

Conditions	Yield
With acetic acid for 2h;	89%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 6-bromo-4-chloro-3-nitroquinoline (723281-72-9) → tert-butyl (R)-3-((6-bromo-3-nitroquinolin-4-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	88.6%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + tert‐butyl 3‐aminopiperidine‐1‐carboxylate (144243-24-3) → tert-butyl 3-((6-bromo-3-nitroquinolin-4-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	88.5%

tert-butyl 4-(4-amino-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate + 6-bromo-4-chloro-3-nitroquinoline (723281-72-9) → tert-butyl 4-(4-((6-bromo-3-nitroquinolin-4-yl)amino)-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate

Conditions	Yield
With sodium acetate; acetic acid at 20℃; for 0.5h;	88%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + 3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester (875798-79-1) → 3-(4-((6-bromo-3-nitroquinolin-4-yl)amino)phenyl)piperidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
With acetic acid at 20℃; for 3h;	87.17%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + 3,5-Dimethoxyaniline (10272-07-8) → 6-bromo-N-(3,5-dimethoxyphenyl)-3-nitroquinolin-4-amine

Conditions	Yield
With sodium acetate; acetic acid at 20℃; for 0.5h;	86%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + C19H22N2O2 → C28H25BrN4O4

Conditions	Yield
With acetic acid for 2h; Reflux;	83.6%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + 4-Aminobenzonitrile (873-74-5) → 4-((6-bromo-3-nitroquinolin-4-yl)amino)benzonitrile

Conditions	Yield
With sodium acetate; acetic acid at 20℃; for 0.5h;	83%
In 1,4-dioxane at 150℃; for 0.166667h; Microwave irradiation;

tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate (170011-57-1) + 6-bromo-4-chloro-3-nitroquinoline (723281-72-9) → 4-(4-((6-bromo-3-nitroquinolin-4-yl)amino)phenyl)piperidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
With acetic acid at 20℃; for 5h;	81.25%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + methyl t-butyl malonate (42726-73-8) → 1-(tert-butyl) 3-methyl 2-(6-bromo-3-nitroquinolin-4-yl)malonate

Conditions	Yield
Stage #1: methyl t-butyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: 6-bromo-4-chloro-3-nitroquinoline In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h; Inert atmosphere;	81%

6-bromo-4-chloro-3-nitroquinoline (723281-72-9) + C19H20N2O2 → C28H23BrN4O4

Conditions	Yield
With acetic acid at 20℃; for 2h;	80%

Upstream product

• 853908-50-6 6-bromo-3-nitroquinolin-4-ol 
• 853908-49-3 5-bromo-2-((2-nitroethenyl)amino)benzoic acid 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 187278-01-9 5-(((4-bromophenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 118-92-3 anthranilic acid 
• 145369-94-4 6-bromoquinolin-4-ol 
• 1551219-53-4 C₁₃H₁₂BrNO₄ 
• 106-40-1 4-bromo-aniline 
• 74189-16-5 2-amino-5-bromobenzoic acid hydrochloride 
• 1201643-75-5 (E)-5-bromo-2-((2-nitrovinyl)amino)benzoic acid 

Downstream Products

• 853908-51-7 {2-[4-(6-bromo-3-nitro-quinolin-4-ylamino)-phenyl]-ethyl}-carbamic acid tert-butyl ester 
• 1201643-76-6 2-(4-((6-bromo-3-nitroquinolin-4-yl)(phenylthio)methyl)phenyl)-2-methylpropanenitrile 
• 915019-52-2 2-[4-(3-amino-6-bromo-quinolin-4-ylamino)-phenyl]-2-methyl-propionitrile 
• 915019-53-3 2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-21-2 2-(4-(8-bromo-2-oxo-3-(4-(trifluoromethoxy)phenylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-25-6 2-(4-(8-bromo-2-oxo-3-(m-tolylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-27-8 2-(4-(8-bromo-3-(2-methyl-5-nitrophenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-30-3 2-(4-(8-bromo-3-(3-fluoro-4-methylphenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-32-5 2-(4-(8-bromo-3-(3,5-dimethylphenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-34-7 2-(4-(8-bromo-2-oxo-3-(phenylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-36-9 2-(4-(8-bromo-2-oxo-3-tosyl-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-38-1 2-(4-(8-bromo-2-oxo-3-(thiophen-2-ylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-40-5 2-(4-(8-bromo-3-(3-fluorophenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-42-7 2-(4-(8-bromo-2-oxo-3-(quinolin-8-ylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 

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