391-82-2

Basic information

• Product Name: 4-CHLORO-7-FLUOROQUINOLINE
• Synonyms: 4-CHLORO-7-FLUOROQUINOLINE
• CAS NO: 391-82-2
• Molecular Formula: C₉H₅ClFN
• Molecular Weight: 181.59
• Mol File: 391-82-2.mol

Chemical Properties

• Melting Point: 73.5-74 °C
• Boiling Point: 259.9°C at 760 mmHg
• Flash Point: 111°C
• Appearance: /
• Density: 1.366g/cm³
• Vapor Pressure: 0.0204mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 2.38±0.27(Predicted)
• CAS DataBase Reference: 4-CHLORO-7-FLUOROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-7-FLUOROQUINOLINE(391-82-2)
• EPA Substance Registry System: 4-CHLORO-7-FLUOROQUINOLINE(391-82-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• Hazardous Substances Data: 391-82-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-7-fluoroquinoline is used as a building block for the synthesis of various pharmaceuticals due to its antimicrobial and antibacterial properties. It plays a crucial role in the development of new drugs and treatments, particularly for infectious diseases caused by bacteria.
Used in Agrochemical Industry:
In the agrochemical sector, 4-chloro-7-fluoroquinoline is utilized as a component in the creation of pesticides and other agricultural chemicals. Its antimicrobial properties make it effective in controlling bacterial infections in crops, thereby enhancing agricultural productivity.
Used in Medicinal Chemistry Research and Development:
4-Chloro-7-fluoroquinoline is employed as a key compound in research and development activities within the field of medicinal chemistry. Its unique structure and reactivity allow for the exploration of new chemical reactions and the synthesis of novel organic compounds with potential therapeutic applications.
Overall, 4-chloro-7-fluoroquinoline's diverse applications across different industries underscore its importance as a versatile chemical compound with significant potential in the development of innovative solutions for various challenges in healthcare, agriculture, and chemical research.

InChI:InChI=1/C9H5ClFN/c10-8-3-4-12-9-5-6(11)1-2-7(8)9/h1-5H

Upstream product

• 26892-97-7 7-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid ethyl ester 
• 183057-56-9 7-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 63463-20-7 7-Fluoro-4-hydroxyquinoline-3-carboxylic acid 
• 26832-95-1 diethyl 2-(((3-fluorophenyl)amino)methylene)malonate 
• 372-19-0 meta-fluoroaniline 
• 86-98-6 4,7-dichloroquinoline 
• 391-83-3 7-fluoro-4-hydroxyquinoline 
• 391-83-3 7-fluoro-1,4-dihydroquinolin-4-one 
• 26892-97-7 ethyl 7-fluoro-4-hydroxy-3-quinolinecarboxylate 

Downstream Products

• 442-96-6 rac-N¹,N¹-diethyl-N⁴-(7-fluoroquinolin-4-yl)pentane-1,4-diamine 
• 1027957-62-5 N²-(7-Fluoro-quinolin-4-yl)-propane-1,2-diamine 

Relevant articles and documents

19F NMR spectroscopy of polyhalonaphthalenes. Part IV. Halex reactions of polychloroquinolines

Nucleophilic fluoride dechlorination of four starting materials (5,6,7,8-tetrachloro-, 3,5,6,7,8-pentachloro-, 4,7-dichloro-, 2,3,4,5,6,7,8-heptachloro-quinoline) led to the preparation of thirteen new polychloropolyfluoroquinolines via reaction with caesium fluoride in DMSO at 100°C. The product from the perchloroquinoline was an inseparable mixture of C9Cl7_nF.nN where n is 1-3. These products were studied in the NMR tube.

Design, synthesis and biological evaluation of new quinoline derivatives as potential antitumor agents

A series of new quinoline derivatives was designed, synthesized and evaluated for their antiproliferative activity. The results demonstrated that compounds 11p, 11s, 11v, 11x and 11y exhibited potent antiproliferative activity with IC50 value of lower than 10 μM against seven human tumor cell lines, and N-(3-methoxyphenyl)-7- (3-phenylpropoxy)quinolin-4-amine 11x was found to be the most potent antiproliferative agent against HCT-116, RKO, A2780 and Hela cell lines with an IC50 value of 2.56, 3.67, 3.46 and 2.71 μM, respectively. The antitumor efficacy of the representative compound 11x in mice was also evaluated, and the results showed that compound 11x effectively inhibited tumor growth and decreased tumor weight in animal models. Further investigation on mechanism of action indicated that compound 11x could inhibit colorectal cancer growth through ATG5-depenent autophagy pathway. Therefore, these quinoline derivatives are a new class of molecules that have the potential to be developed as new antitumor drugs.

PHOSPHONATE-CHLOROQUINE CONJUGATES AND METHODS USING SAME

The present invention provides compositions and methods for providing controllable local delivery of a conjugate of chloroquine (CQ) and a bisphosphonate to treat diseases characterized by abnormal bone metabolism. In certain embodiments, the invention is used as a treatment for a subject with diseases and disorders characterized by bone loss.

Synthesis and anti-tumor activities of 4-anilinoquinoline derivatives

Twenty-two 7-fluoro (or 8-methoxy)-4-anilinoquinolines compounds were designed and synthesized as potentially potent and selective antitumor inhibitors. All the prepared compounds were evaluated for their in vitro antiproliferative activities against the HeLa and BGC823 cell lines. Ten compounds (1a-g; 2c; 2e and 2i) exhibited excellent antitumor activity superior to that of gefitinib. Among the ten compounds; seven (1a-c; 1e-1g and 2i) displayed excellent selectivity for BGC823 cells. In particular; 1f and 2i exhibited potent cytotoxic activities against HeLa cells and BGC823 cells with better IC50 values than gefitinib.

QUINOLINE DERIVATIVES

The invention concerns quinoline derivatives of Formula (I): or a pharmaceutically-acceptable salt thereof, wherein each of X1, p, R1, q, R2, R3, R4, R5, Ring A, r and R6 has any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the treatment of cell proliferative disorders.

QUINOLINE DERIVATIVES FOR TREATING CANCER

The invention concerns quinoline derivatives of Formula (I) or a pharmaceutically-acceptable salt thereof, wherein each of X1, p, R1, q, R2, R3, R4, R5, Ring A, r and R6 has any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the treatment of cell proliferative disorders.

Structure-activity relationships for antiplasmodial activity among 7- substituted 4-aminoquinolines

Aminoquinolines (AQs) with diaminoalkane side chains (-HNRNEt2) shorter or longer than the isopentyl side chain [-HNCHMe(CH2)3NEt2] of chloroquine are active against both chloroquine-susceptible and -resistant Plasmodium falciparum. (De, D.; et al. Am. J. Trop. Med. Hyg. 1996, 55, 579-583). In the studies reported here, we examined structure-activity relationships (SARs) among AQs with different N,N-diethyldiaminoalkane side chains and different substituents at the 7-position occupied by Cl in chloroquine. 7-Iodo- and 7- bromo-AQs with diaminoalkane side chains [-HN(CH2)2NEt2, -HN(CH2)3NEt2, or -HNCHMeCH2NEt2] were as active as the corresponding 7-chloro-AQs against both chloroquine-susceptible and -resistant P. falciparum (IC50s of 3-12 nM). In contrast, with one exception, 7-fluoro-AQs and 7-trifluoromethyl-AQs were less active against chloroquine-susceptible P. falciparum (IC50s of 15-50 nM) and substantially less active against chloroquine-resistant P. falciparum (IC50s of 18-500 nM). Furthermore, most 7-OMe-AQs were inactive against both chloroquine-susceptible (IC50s of 17-150 nM) and -resistant P. falciparum (IC50s of 90-3000 nM).