346-55-4

Basic information

• Product Name: 4-Chloro-7-(trifluoromethyl)quinoline
• Synonyms: BUTTPARK 15\09-27;4-CHLORO-7-(TRIFLUOROMETHYL)QUINOLINE;Quinoline, 4-chloro-7-(trifluoromethyl)-;4-CHLORO-7-(TRIFLUOROMETHYL)QUINOLINE, 9 8%;4-Chloro-7-(trifluoromethyl)quinoline 98%;4-Chloro-7-(trifluoroMethyl)quin
• CAS NO: 346-55-4
• Molecular Formula: C₁₀H₅ClF₃N
• Molecular Weight: 231.6
• EINECS: 206-471-0
• Product Categories: Quinoline&Isoquinoline;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinolines;QuinolinesHeterocyclic Building Blocks
• Mol File: 346-55-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 69-71 °C(lit.)
• Boiling Point: 265.51 °C at 760 mmHg
• Flash Point: 114.377 °C
• Appearance: white to light yellow crystal powder
• Density: 1.4120 (estimate)
• Vapor Pressure: 7.2E-08mmHg at 25°C
• Refractive Index: 1.487
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: chloroform: soluble25mg/mL, clear, colorless
• PKA: 1.18±0.27(Predicted)
• CAS DataBase Reference: 4-Chloro-7-(trifluoromethyl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-7-(trifluoromethyl)quinoline(346-55-4)
• EPA Substance Registry System: 4-Chloro-7-(trifluoromethyl)quinoline(346-55-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 346-55-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

4-Chloro-7-(trifluoromethyl)quinoline is a reagent in the preparation of piperazinylquinolines as breast cancer inhibitors.

InChI:InChI=1/C15H18F3NO4/c1-14(2,3)23-13(22)19-11(12(20)21)8-9-6-4-5-7-10(9)15(16,17)18/h4-7,11H,8H2,1-3H3,(H,19,22)(H,20,21)

Upstream product

• 98-16-8 3-trifluoromethylaniline 
• 128403-22-5 2-nitro-4-trifluoromethyl-acetophenone 
• 37885-07-7 1-(2-amino-4-(trifluoromethyl)phenyl)ethanone 
• 370-35-4 diethyl 2-({[3-(trifluoromethyl)phenyl]amino}methylidene)propanedioate 
• 391-02-6 4-hydroxy-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester 
• 574-92-5 4-hydroxy-7-(trifluoromethyl)-3-quinolinecarboxylic acid 
• 25063-55-2 2,2-dimethyl-5-{[(3-trifluoromethylphenyl)amino]methylene}-1,3-dioxane-4,6-dione 
• 3724-43-4 Vilsmeier reagent 
• 128403-24-7 N'-(2-Acetyl-5-trifluoromethyl-phenyl)-N,N-dimethyl-formamidine; hydrochloride 
• 128403-23-6 N-(2-Acetyl-5-trifluoromethyl-phenyl)-formamide 
• 322-97-4 7-trifluoromethyl-quinolin-4-ol 

Downstream Products

• 71916-56-8 4-(3-methylphenyl)-4-hydroxy-1-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperidine 
• 71916-53-5 4-phenyl-1-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]-benzoyl]piperidine 
• 71916-51-3 4-(3-methylphenyl)-1,2,5,6-tetrahydro-1-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]pyridine 
• 71916-59-1 4-(4-methoxyphenyl)-1,2,5,6-tetrahydro-1-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]pyridine 
• 71916-54-6 4-(4-chlorophenyl)-1-<4-<<7-(trifluoromethyl)-4-quinolinyl>amino>benzoyl>piperidinol 
• 71916-55-7 4-(4-methoxyphenyl)-4-hydroxy-1-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperidine 
• 95257-88-8 4-<3,5-bis<(N-pyrrolidinyl)methyl>-4-hydroxyanilino>-7-(trifluoromethyl)quinoline 
• 71916-50-2 Imidazol-1-yl-[4-(7-trifluoromethyl-quinolin-4-ylamino)-phenyl]-methanone 
• 98859-10-0 1-phenyl-4-amino>benzoyl>piperazine 
• 98874-76-1 [4-(4-Methoxy-phenyl)-piperazin-1-yl]-[4-(7-trifluoromethyl-quinolin-4-ylamino)-phenyl]-methanone 
• 243666-11-7 7-trifluoromethyl-quinolin-4-ylamine 
• 49713-58-8 4‐chloroquinoline‐7‐carboxylic acid 
• 222734-72-7 7-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline hydrochloride 
• 95257-90-2 2,6-bis(morpholin-1-ylmethyl)-4-(7'-trifluoromethylquinolin-4'-ylamino)phenol 

Relevant articles and documents

Design, synthesis and biological evaluation of 4-aminoquinoline-guanylthiourea derivatives as antimalarial agents

Guanylthiourea (GTU) has been identified as an important antifolate antimalarial pharmacophore unit, whereas, 4-amino quinolones are already known for antimalarial activity. In the present work molecules carrying 4-aminoquinoline and GTU moiety have been designed using molecular docking analysis with PfDHFR enzyme and heme unit. The docking results indicated that the necessary interactions (Asp54 and Ile14) and docking score (?9.63 to ?7.36 kcal/mmol) were comparable to WR99210 (?9.89 kcal/mol). From these results nine molecules were selected for synthesis. In vitro analysis of these synthesized compounds reveal that out of the nine molecules, eight show antimalarial activity in the range of 0.61–7.55 μM for PfD6 strain and 0.43–8.04 μM for PfW2 strain. Further, molecular dynamics simulations were performed on the most active molecule to establish comparative binding interactions of these compounds and reference ligand with Plasmodium falciparum dihydrofolate reductase (PfDHFR).

Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities

A simple two-step synthesis method was used to make 51 B-ring-substituted 4-hydroxyquinolines allowing analysis of the effect of ring substitutions on inhibition of growth of chloroquine sensitive and resistant strains of Plasmodium falciparum, the dominant cause of malaria morbidity. Substituted quinoline rings other than the 7-chloroquinoline ring found in chloroquine were found to have significant activity against the drug-resistant strain of P. falciparum W2.

NOVEL QUINOLINE DERIVATIVES

The invention relates to compounds represented by Formula (I): and to pharmaceutically acceptable salts or solvates of said compounds, wherein each of A, R3-8, X3, X5, m, and n are defined herein. The invention also relates to pharmaceutical compositions containing the compounds of Formula (I) and to methods of treating hyperproliferative disorders in a mammal by administering compounds of Formula (I).