85-81-4

Basic information

• Product Name: 6-METHOXY-8-NITROQUINOLINE
• Synonyms: 6-methoxy-8-nitro-quinolin;8-Nitro-6-methoxyquinoline;Quinoline, 6-methoxy-8-nitro-;6-METHOXY-8-NITROQUINOLINE;methyl 8-nitro-6-quinolyl ether;6-METOXY-8-NITROQUINOLINE,99%;6-methoxy-8-nitro-quinolin6-methoxy-8-nitroquinoline;6-Methoxy-8-nitroquinoline, GC 99%
• CAS NO: 85-81-4
• Molecular Formula: C10H8N2O3
• Molecular Weight: 204.18
• EINECS: 201-633-7
• Product Categories: Quinoline&Isoquinoline;Building Blocks;Heterocyclic Building Blocks;Quinolines;Intermediates
• Mol File: 85-81-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 158-160 °C(lit.)
• Boiling Point: 342.67°C (rough estimate)
• Flash Point: 179.4°C
• Appearance: Yellow/Crystalline Powder
• Density: 1.3244 (rough estimate)
• Vapor Pressure: 1.97E-05mmHg at 25°C
• Refractive Index: 1.5910 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.25±0.20(Predicted)
• CAS DataBase Reference: 6-METHOXY-8-NITROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-8-NITROQUINOLINE(85-81-4)
• EPA Substance Registry System: 6-METHOXY-8-NITROQUINOLINE(85-81-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-40
• Safety Statements: 26-27-36/37/39
• WGK Germany: 3
• RTECS: VC0365000
• Hazardous Substances Data: 85-81-4(Hazardous Substances Data)

Usage

Chemical Properties

YELLOW CRYSTALLINE POWDER

Uses

6-Methoxy-8-nitroquinoline is used in treating and preventing pancreatic cancer. Also, used in preparation of Quinoline derivatives as antiparasitic agents useful in the prophylaxis and treatment of malaria and parasitic diseases.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1569, 1946 DOI: 10.1021/ja01212a057Organic Syntheses, Coll. Vol. 3, p. 568, 1955

InChI:InChI=1/C10H8N2O3/c1-15-8-5-7-3-2-4-11-10(7)9(6-8)12(13)14/h2-6H,1H3

Upstream product

• 119-81-3 4-methoxy-2-nitroacetanilide 
• 56-81-5 glycerol 
• 96-96-8 4-methoxy-2-nitroaniline 
• 51-66-1 4-methoxyacetanilide 
• 104-94-9 4-methoxy-aniline 
• 4280-28-8 3,4-dinitroanisole 
• 2806-85-1 3-ethoxypropanal 
• 86119-84-8 phosphoric acid 
• 7778-39-4 orthoarsenic acid 
• 107-02-8 acrolein 

Downstream Products

• 90-52-8 6-methoxyquinolin-8-amine 
• 57742-99-1 6-methoxy-8-(hydroxyamino)quinoline 
• 63460-48-0 N⁴-(5-(4-fluorophenoxy)-6-methoxyquinolin-8-yl)pentane-1,4-diamine 
• 57514-26-8 N⁴-(6-methoxy-5-(4-chlorophenoxy)quinolin-8-yl)pentane-1,4-diamine 
• 63460-34-4 5-(4-fluoro-phenoxy)-6-methoxy-8-nitro-quinoline 

Relevant articles and documents

-

-

8-amino-6-methoxyquinoline—tetrazole hybrids: Impact of linkers on antiplasmodial activity

A new series of compounds was prepared from 6-methoxyquinolin-8-amine or its N-(2-aminoethyl) analogue via Ugi-azide reaction. Their linkers between the quinoline and the tert-butyltetrazole moieties differ in chain length, basicity and substitution. Compounds were tested for their antiplasmodial activity against Plasmodium falciparum NF54 as well as their cytotoxicity against L-6-cells. The activity and the cytotoxicity were strongly influenced by the linker and its substitution. The most active compounds showed good activity and promising selectivity.

Uncatalyzed, on water oxygenative cleavage of inert C-N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives

Oxygenative cleavage of an inert CAr-NH2 bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is reported in water at room temperature. The reaction is highly atom- and step-economical as both C- and N-containing fragments of the C-N bond cleavage are incorporated into the target molecule and is effected without the need for N-oxide. The reaction is scalable to gram level, and the products are useful as electrophilic partners for coupling reactions, ligands in catalysis and bioactive compounds.