133860-75-0

Basic information

• Product Name: 2-chloro-N-(2-methylpropyl)-3-nitroquinolin-4-amine
• Synonyms: 2-chloro-N-(2-methylpropyl)-3-nitroquinolin-4-amine;2-Chloro-N-(2-methylpropyl)-3-nitro-4-quinolinamine;Intermediate F of Imiquimod;2-chloro-N4-(2-methylpropyl)-3-nitroquinoline-4-amine
• CAS NO: 133860-75-0
• Molecular Formula: C₁₃H₁₄ClN₃O₂
• Molecular Weight: 279.72216
• Mol File: 133860-75-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 85-88 °C(Solv: propyl acetate (109-60-4))
• Boiling Point: 427.65°C at 760 mmHg
• Flash Point: 212.435°C
• Appearance: /
• Density: 1.333g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.656
• PKA: -0.47±0.50(Predicted)
• CAS DataBase Reference: 2-chloro-N-(2-methylpropyl)-3-nitroquinolin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-N-(2-methylpropyl)-3-nitroquinolin-4-amine(133860-75-0)
• EPA Substance Registry System: 2-chloro-N-(2-methylpropyl)-3-nitroquinolin-4-amine(133860-75-0)

Safety Data

• Hazardous Substances Data: 133860-75-0(Hazardous Substances Data)

Usage

Uses

2-Chloro-N-(2-methylpropyl)-3-nitroquinolin-4-amine is used in preparation of Amine compounds having anti-inflammatory, antifungal, antiparasitic and anticancer activity. Is also used in preparation of Imiquimod from Dihydroxyquinoline.

InChI:InChI=1/C13H14ClN3O2/c1-8(2)7-15-11-9-5-3-4-6-10(9)16-13(14)12(11)17(18)19/h3-6,8H,7H2,1-2H3,(H,15,16)

Upstream product

• 15151-57-2 4-hydroxy-3-nitro-1,2-dihydroquinolin-2-one 
• 78-81-9 isobutylamine 
• 15151-57-2 2,4-dihydroxy-3-nitroquinoline 
• 70254-44-3 2,4-dihydroxyquinoline 
• 132521-66-5 2,4-dichloro-3-nitroquinoline 

Downstream Products

• 133860-76-1 2-chloro-N⁴-(2-methylpropyl)quinoline-3,4-diamine 
• 1025814-34-9 N-(2-chloro-4-isobutylamino-quinolin-3-yl)-2-phenoxy-acetamide 
• 99011-02-6 imiqimod 
• 1508303-97-6 5-chloro-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-98-7 5-iodo-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-93-2 2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-94-3 3-bromo-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-95-4 5-bromo-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 
• 1508303-96-5 4-chloro-2-[(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]benzoic acid 

Relevant articles and documents

Synthesis of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as potent antiproliferative agents via a hybrid pharmacophore approach

Imiquimod (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine) is efficacious in topical therapy for certain types of skin cancers. Structurally similar EAPB0203 (N-methyl-1-(2-phenethyl)imidazo[1,2-a]quinoxalin-4-amine) has been shown higher in vitro potency than imiquimod. Besides, triazole, oxadiazole, and thiadiazole rings are privileged building blocks in drug design. A series of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole and [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-thiadiazole derivatives were therefore synthesized by incorporation of these rings into the structure of EAPB0203 and assessed their antiproliferative effects against various cancer cell lines. The 1,3,4-oxadiazole derivatives demonstrated the superior effectiveness compared to imiquimod and EAPB0203. Our findings highlight the excellent potential of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as anticancer agents.

AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC AND ANTICANCER ACTIVITY

Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.

3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines

A process for the preparation of 1-substituted, 4-substituted-1H-imidazo[4,5-c]quinolines, intermediates in the preparation of such compounds, and processes for the preparation of such intermediates.