80947-25-7

Basic information

• Product Name: 4-AMINO-2-CHLOROQUINOLINE
• Synonyms: 4-AMINO-2-CHLOROQUINOLINE;2-Chloroquinolin-4-amine;(2-Chloroquinolin-4-yl)amine;2-Chloro-4-quinolinamine;4-Quinolinamine,2-chloro-
• CAS NO: 80947-25-7
• Molecular Formula: C₉H₇ClN₂
• Molecular Weight: 178.61828
• Product Categories: API intermediates
• Mol File: 80947-25-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 250℃
• Boiling Point: 366℃
• Flash Point: 175℃
• Appearance: /
• Density: 1.363
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.712
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.24±0.50(Predicted)
• CAS DataBase Reference: 4-AMINO-2-CHLOROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-2-CHLOROQUINOLINE(80947-25-7)
• EPA Substance Registry System: 4-AMINO-2-CHLOROQUINOLINE(80947-25-7)

Safety Data

• Hazardous Substances Data: 80947-25-7(Hazardous Substances Data)

Usage

General Description

4-AMINO-2-CHLOROQUINOLINE is a chemical compound with the molecular formula C9H7ClN2. It is an aminoquinoline derivative and is commonly used in the synthesis of various pharmaceutical drugs, particularly antimalarial agents. The compound is known for its potent antimalarial activity and is used as a building block in the production of antimalarial drugs such as chloroquine and amodiaquine. 4-AMINO-2-CHLOROQUINOLINE can also be used in the synthesis of fluorescent dyes and as a precursor in organic chemistry reactions. Its chemical structure and properties make it an important intermediate in the pharmaceutical and chemical industries.

InChI:InChI=1/C9H7ClN2/c10-9-5-7(11)6-3-1-2-4-8(6)12-9/h1-5H,(H2,11,12)

Upstream product

• 157027-30-0 4-azido-2-chloro-quinoline 
• 4295-16-3 2-chloroquinoline-4-carboxamide 
• 2508-86-3 4-aminoquinoline 1-oxide 
• 703-61-7 2,4-dichloroquinoline 
• 2388-32-1 2-chloroquinoline-4-carbonyl chloride 
• 15733-89-8 2-hydroxyquinoline-4-carboxylic acid 
• 1010-61-3 N-(1-oxy-[4]quinolyl)-hydroxylamine; hydrochloride 

Downstream Products

• 1116652-03-9 N-(2-chloroquinolin-4-yl)benzamide 
• 1116652-02-8 N-(2-chloroquinolin-4-yl)cyclohexanecarboxamide 
• 1245211-31-7 C₂₀H₁₄ClN₅O 
• 1245211-33-9 C₂₁H₁₆ClN₅O₂ 
• 1245211-22-6 C₁₇H₁₃Cl₂N₃O₂ 

Relevant articles and documents

Efficient synthesis, fluorescence and DFT studies of different substituted 2-chloroquinoline-4-amines and benzo[g][1,8]naphthyridine derivatives

An efficient and single step strategy for synthesizing new functionalized benzo[b][1,8]naphthyridine derivatives is presented. Benzo[g][1,8]naphthyridines have been synthesized by the condensation of substituted 2-chloroquinoline-3-carbaldehydes with various 2-chloroquinoline-4-amines, 1H-Indazole-6-amine in basic medium. The electro luminescence and photophysical properties of a series of benzo[g][1,8]naphthyridines 5(a–d), 6(a–d) and 2-chloroquinoline-4-amines 3(a–f) are reported and investigated with the aim of arriving at good fluorescent materials. Moreover, the effect of electron donor-acceptor substituent on fluorescence properties of all molecules has been investigated along with their fluorescent quantum yields. Furthermore we analyzed for band gap energy associated with HOMO-LUMO, through density functional (DFT M06-HF) studies. The experimental observations are in close agreement with the theoretical calculation. All the synthesized compounds were identified on the basis of their NMR, Mass spectral data analyses.

A3 ADENOSINE RECEPTOR ALLOSTERIC MODULATORS

The present invention provides 2,4-disubstituted quinoline derivatives being an A3 adenosine receptor modulator (A3RM), for use in the treatment of a condition which is treatable by adenosine, an A3 adenosine receptor (A3AR) agonist or an A3 adenosine receptor antagonist. In one embodiment, the 2,4-disubstituted quinoline derivatives are for use in the treatment of a condition treatable by an adenosine or an A3AR agonist, treatment being achieved by enhancing activity of a protein (by binding of said 2,4 disubstituted quinoline derivative to the A3AR). Some conditions treatable by the 2,4 disubstituted quinoline derivative when used for enhancing activity include, malignancy, an immuno-compromised affliction, high intraocular pressure or a condition associated with high intraocular pressure. The invention also provides method for treatment of a subject having a condition treatable by adenosine, an A3AR agonist or an A3AR antagonist making use of the defined 2,4-disubstituted quinoline derivative (s), and pharmaceutical composition and comprising said derivative and a kit comprising the derivative and instructions for use thereof. One specific 2,4-disubstituted quinoline derivative comprises N-{2-[(3,4-dichlorophenyl)amino]quinolin-4-yl}cyclohexanecarboxamide In one embodiment, the 2,4-disubstituted quinoline derivatives in accordance with the invention are formulated in a form suitable for oral administration.

Polarization of heterocyclic rings with aromatic character. CXVIII. 4-Hydroxyaminoquinoline-N-oxide.

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