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5323-58-0 Usage

Description

6-methoxy-8-nitroquinolin-5(1H)-one is a chemical compound with the molecular formula C10H8N2O4. It is a derivative of quinolinone, characterized by the presence of a methoxy group at the 6 position and a nitro group at the 8 position of the quinoline ring. 6-methoxy-8-nitroquinolin-5(1H)-one is used in organic synthesis and medicinal chemistry, and has been studied for its potential pharmacological activities, including antimicrobial and antitumor properties. Its structure and properties make 6-methoxy-8-nitroquinolin-5(1H)-one a promising candidate for further pharmaceutical research and development.

Uses

Used in Organic Synthesis:
6-methoxy-8-nitroquinolin-5(1H)-one is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique functional groups allow for versatile chemical reactions, making it a valuable intermediate in the synthesis of pharmaceuticals and other organic compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-methoxy-8-nitroquinolin-5(1H)-one is used as a lead compound for the development of new drugs. Its pharmacological properties, such as antimicrobial and antitumor activities, make it a promising candidate for the treatment of various diseases.
Used in Antimicrobial Applications:
6-methoxy-8-nitroquinolin-5(1H)-one is used as an antimicrobial agent, exhibiting activity against a range of bacteria and other microorganisms. Its ability to disrupt essential cellular processes in these organisms makes it a potential candidate for the development of new antimicrobial drugs.
Used in Antitumor Applications:
6-methoxy-8-nitroquinolin-5(1H)-one is used as an antitumor agent, showing potential in the treatment of various types of cancer. Its ability to inhibit the growth and proliferation of tumor cells makes it a promising candidate for further research and development in oncology.
Used in Pharmaceutical Research and Development:
6-methoxy-8-nitroquinolin-5(1H)-one is used as a research tool in the pharmaceutical industry for the discovery and development of new drugs. Its unique structure and properties provide a foundation for the design and synthesis of novel therapeutic agents with improved efficacy and selectivity.

Check Digit Verification of cas no

The CAS Registry Mumber 5323-58-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,2 and 3 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5323-58:
(6*5)+(5*3)+(4*2)+(3*3)+(2*5)+(1*8)=80
80 % 10 = 0
So 5323-58-0 is a valid CAS Registry Number.

5323-58-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-methoxy-8-nitro-1H-quinolin-5-one

1.2 Other means of identification

Product number -
Other names 5-Hydroxy-6-methoxy-8-nitro-chinolin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5323-58-0 SDS

5323-58-0Synthetic route

5,6-dimethoxy-8-nitroquinoline
5333-02-8

5,6-dimethoxy-8-nitroquinoline

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water90%
With potassium hydroxide
With hydrogenchloride
With hydrogenchloride
N-(6-methoxy-8-nitro-[5]quinolyl)-acetamide

N-(6-methoxy-8-nitro-[5]quinolyl)-acetamide

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

Conditions
ConditionsYield
With sodium hydroxide
5-fluoro-4-methoxy-2-nitroaniline
446-20-8

5-fluoro-4-methoxy-2-nitroaniline

glycerol
56-81-5

glycerol

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

Conditions
ConditionsYield
With arsenic(V) oxide; sulfuric acid at 130 - 140℃;
N-(5-fluoro-4-methoxy-2-nitrophenyl)acetamide
448-26-0

N-(5-fluoro-4-methoxy-2-nitrophenyl)acetamide

glycerol
56-81-5

glycerol

A

5-fluoro-6-methoxy-8-nitroquinoline
316-77-8

5-fluoro-6-methoxy-8-nitroquinoline

B

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

Conditions
ConditionsYield
With arsenic(V) oxide; sulfuric acid
1-fluoro-2-methoxybenzene
321-28-8

1-fluoro-2-methoxybenzene

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid anhydride; glacial acetic acid; HNO3 / -10 - 0 °C
2: platinum / Hydrogenation
3: concentrated sulfuric acid; water; nitric acid
4: arsenic (v)-oxide; sulfuric acid
View Scheme
2-fluoro-1-methoxy-4-nitrobenzene
455-93-6

2-fluoro-1-methoxy-4-nitrobenzene

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: platinum / Hydrogenation
2: concentrated sulfuric acid; water; nitric acid
3: arsenic (v)-oxide; sulfuric acid
View Scheme
N-(3-fluoro-4-methoxyphenyl)acetamide
452-15-3

N-(3-fluoro-4-methoxyphenyl)acetamide

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated sulfuric acid; water; nitric acid
2: arsenic (v)-oxide; sulfuric acid
View Scheme
4-Acetylamino-1,2-dimethoxy-5-nitrobenzene
99069-17-7

4-Acetylamino-1,2-dimethoxy-5-nitrobenzene

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: arsenic (V)-oxide; concentrated sulfuric acid
2: aq.-ethanolic hydrochloric acid
View Scheme
1-bromo-octane
111-83-1

1-bromo-octane

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

6-Methoxy-8-nitro-5-(n-octoxy)quinoline
81359-03-7

6-Methoxy-8-nitro-5-(n-octoxy)quinoline

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; triethylamine; methyloxirane at 140 - 150℃; for 2.5h;75%
With triethylamine; methyloxirane In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether
amyl iodide
628-17-1

amyl iodide

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

6-Methoxy-8-nitro-5-pentyloxy-quinoline
108190-29-0

6-Methoxy-8-nitro-5-pentyloxy-quinoline

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; triethylamine; methyloxirane at 140 - 150℃; for 2.5h;73%
1-bromo-butane
109-65-9

1-bromo-butane

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

5-(n-Butoxy)-6-methoxy-8-nitroquinoline
81358-76-1

5-(n-Butoxy)-6-methoxy-8-nitroquinoline

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; triethylamine; methyloxirane at 140 - 150℃; for 2.5h;70%
With triethylamine In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water
1-bromo-hexane
111-25-1

1-bromo-hexane

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

5-(n-Hexoxy)-6-methoxy-8-nitroquinoline
81358-87-4

5-(n-Hexoxy)-6-methoxy-8-nitroquinoline

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; triethylamine; methyloxirane at 140 - 150℃; for 2.5h;65%
With triethylamine; methyloxirane In N,N,N,N,N,N-hexamethylphosphoric triamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

propyl bromide
106-94-5

propyl bromide

6-methoxy-8-nitro-5-(n-propoxy)quinoline
81358-71-6

6-methoxy-8-nitro-5-(n-propoxy)quinoline

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; triethylamine; methyloxirane at 140 - 150℃; for 2.5h;62%
With triethylamine; methyloxirane In N,N,N,N,N,N-hexamethylphosphoric triamide; water11.1 grams (62%)
Iododecane
2050-77-3

Iododecane

6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

5-decoxy-6-methoxy-8-nitroquinoline
81359-08-2

5-decoxy-6-methoxy-8-nitroquinoline

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; triethylamine; methyloxirane at 140 - 150℃; for 2.5h;56%
With triethylamine; methyloxirane In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

acetic anhydride
108-24-7

acetic anhydride

5-acetoxy-8-acetylamino-6-methoxy-quinoline

5-acetoxy-8-acetylamino-6-methoxy-quinoline

Conditions
ConditionsYield
With acetic acid; zinc
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

5-chloro-6-methoxy-8-nitro-quinoline
64992-86-5

5-chloro-6-methoxy-8-nitro-quinoline

Conditions
ConditionsYield
With trichlorophosphate
With trichlorophosphate43 g (97%)
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

8-Amino-5-(n-hexoxy)-6-methoxyquinoline
81358-88-5

8-Amino-5-(n-hexoxy)-6-methoxyquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

8-amino-6-methoxy-5-(n-octoxy)quinoline
81359-04-8

8-amino-6-methoxy-5-(n-octoxy)quinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 89 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

8-Amino-5-(n-decoxy)-6-methoxyquinoline
81359-09-3

8-Amino-5-(n-decoxy)-6-methoxyquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 56 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 54 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

6-methoxy-8-(1-methyl-4-phthalimidobutylamino)-5-(n-propoxy)quinoline
81358-73-8

6-methoxy-8-(1-methyl-4-phthalimidobutylamino)-5-(n-propoxy)quinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 62 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 72 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

5-(n-Butoxy)-6-methoxy-8-(1-methyl-4-phthalimidobutylamino)quinoline
81358-78-3

5-(n-Butoxy)-6-methoxy-8-(1-methyl-4-phthalimidobutylamino)quinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 70 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 82 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

2-[4-(6-Methoxy-5-pentyloxy-quinolin-8-ylamino)-pentyl]-isoindole-1,3-dione
108190-69-8

2-[4-(6-Methoxy-5-pentyloxy-quinolin-8-ylamino)-pentyl]-isoindole-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 73 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 82 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

5-(n-Hexoxy)-6-methoxy-8-(1-methyl-4-phthalimidobutylamino)quinoline
81358-89-6

5-(n-Hexoxy)-6-methoxy-8-(1-methyl-4-phthalimidobutylamino)quinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 65 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

6-Methoxy-8-(1-methyl-4-phthalimidobutylamino)-5-(n-octoxy)quinoline
81359-05-9

6-Methoxy-8-(1-methyl-4-phthalimidobutylamino)-5-(n-octoxy)quinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 75 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 89 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

5-(n-Decoxy)-6-methoxy-8-(1-methyl-4-phthalimidobutylamino)quinoline
81359-10-6

5-(n-Decoxy)-6-methoxy-8-(1-methyl-4-phthalimidobutylamino)quinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 56 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 54 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

N4-(6-Methoxy-5-propoxy-quinolin-8-yl)-pentane-1,4-diamine
81358-74-9

N4-(6-Methoxy-5-propoxy-quinolin-8-yl)-pentane-1,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 62 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 72 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
4: 95percent aq. H2NNH2 / ethanol / 4.5 h / Heating
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

N4-(5-Butoxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine
81358-79-4

N4-(5-Butoxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 70 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 82 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
4: 95percent aq. H2NNH2 / ethanol / 4.5 h / Heating
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

N4-(6-Methoxy-5-pentyloxy-quinolin-8-yl)-pentane-1,4-diamine
108190-09-6

N4-(6-Methoxy-5-pentyloxy-quinolin-8-yl)-pentane-1,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 73 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 82 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
4: 95percent aq. H2NNH2 / ethanol / 4.5 h / Heating
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

N4-(5-Hexyloxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine
81358-90-9

N4-(5-Hexyloxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 65 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
4: 95percent aq. H2NNH2 / ethanol / 4.5 h / Heating
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

N4-(6-Methoxy-5-octyloxy-quinolin-8-yl)-pentane-1,4-diamine
81359-06-0

N4-(6-Methoxy-5-octyloxy-quinolin-8-yl)-pentane-1,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 75 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 89 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
4: 95percent aq. H2NNH2 / ethanol / 4.5 h / Heating
View Scheme
6-methoxy-8-nitro-quinolin-5-ol
5323-58-0

6-methoxy-8-nitro-quinolin-5-ol

N4-(5-Decyloxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine
81359-11-7

N4-(5-Decyloxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 56 percent / triethylamine, hexamethylphosphoric triamide, propylene oxide / 2.5 h / 140 - 150 °C
2: 54 percent / Fe, AcOH / H2O; dibutyl ether / 6 h / 100 °C
3: Et3N / 4.5 h / 140 - 150 °C
4: 95percent aq. H2NNH2 / ethanol / 4.5 h / Heating
View Scheme

5323-58-0Upstream product

5323-58-0Downstream Products

5323-58-0Relevant articles and documents

5-(Straight chain 3-12 carbon alkoxy)-8-quinolinamines and their use for treatment of malaria

-

, (2008/06/13)

Improved means for the chemotherapy of malaria have been achieved with 5-oxy-primaquine analogues having the formula: STR1 wherein R4 represents hydrogen or a methyl grouping, and R represents an alkyl group containing 3 to 12 carbon atoms and pharmaceutically acceptable salts thereof, wherein the salt-forming acid may be organic or inorganic in nature. These primaquine-related compounds afford improvement in the chemotherapy of malaria by exerting plasmodicidal action on malaria parasites which may be present in either the blood, formed tissues, or blood and formed tissues of the mammalian host. Such broad and practical spectrum of effectiveness distinguishes the said primaquine analogues, which may be administered parenterally or perorally to infected animals.

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