703-61-7

Basic information

• Product Name: 2,4-DICHLOROQUINOLINE
• Synonyms: 2,4-DICHLOROQUINOLINE;AURORA KA-3862;IFLAB-BB F1706-0118;2,4-Dichloroquinoline 98%;2,4-dichloroquinoline(SALTDATA: FREE);2-4-Dichloro-1-azanaphthalene;Quinoline,2,4-dichloro-
• CAS NO: 703-61-7
• Molecular Formula: C₉H₅Cl₂N
• Molecular Weight: 198.05
• EINECS: 1312995-182-4
• Product Categories: pharmacetical
• Mol File: 703-61-7.mol
• Article Data: 49

Chemical Properties

• Melting Point: 52-54
• Boiling Point: 282°C(lit.)
• Flash Point: 154.2 °C
• Appearance: /
• Density: 1.4178 (rough estimate)
• Vapor Pressure: 0.00623mmHg at 25°C
• Refractive Index: 1.6610 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• PKA: -1.10±0.50(Predicted)
• CAS DataBase Reference: 2,4-DICHLOROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DICHLOROQUINOLINE(703-61-7)
• EPA Substance Registry System: 2,4-DICHLOROQUINOLINE(703-61-7)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-41-37/38-25
• Safety Statements: 26-36-45-39
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 703-61-7(Hazardous Substances Data)

Usage

Description

2,4-Dichloroquinoline is an organic compound with the chemical formula C9H5Cl2N. It is a derivative of quinoline, which is a heterocyclic aromatic compound containing a nitrogen atom in a six-membered ring fused to a seven-membered ring. The presence of two chlorine atoms at the 2nd and 4th positions of the quinoline ring gives 2,4-dichlorquinoline its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
2,4-Dichloroquinoline is used as a key intermediate in the synthesis of tRNA synthetase inhibitors. These inhibitors exhibit antibacterial activity, particularly against gram-positive bacteria. The inhibition of tRNA synthetase disrupts protein synthesis in bacteria, leading to their growth inhibition and eventual death.
Used in Veterinary Medicine:
In the veterinary medicine industry, 2,4-dichlorquinoline is used in the preparation of arylquinolines, which display anthelmintic properties. These compounds are effective against various helminths, including intestinal worms and parasites, and are used to treat infections in animals.
Overall, 2,4-dichlorquinoline plays a significant role in the development of new drugs and therapeutic agents, particularly in the fields of antibacterial and anthelmintic treatments. Its unique chemical structure and reactivity make it a valuable compound for the synthesis of various pharmaceuticals and bioactive molecules.

Synthesis

The synthesis of 2,4-dichloroquinoline is as follows:A suspension of quinoline-2,4-diol (150 g, 931 mmol) in POCl3?(975 mL, 10.4 mol) was stirred at reflux for 6 hr and the reaction mixture was concentrated. The residue was diluted with CHCl3?(500 mL) and the solution was poured into ice water. The aqueous layer was extracted with CHCl3?(three times). The combined organic layer was dried over MgSO4, filtrated, concentrated, and purified by flash chromatography (silica gel, 20% EtOAc in hexane) to give 2,4-dichloroquinoline (177 g, 96%) as a pale brown solid.

InChI:InChI=1/C9H5Cl2N/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5H

Upstream product

• 10285-97-9 α-oxyquinoline 1-oxide 
• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 
• 56-57-5 4-nitroquinoline-N-oxide 
• 101273-92-1 1-benzyloxy-1H-quinolin-4-one 
• 70254-43-2 4-Hydroxy-2-quinolone 
• 141-82-2 malonic acid 
• 62-53-3 aniline 
• 151387-00-7 2,4-dichloroquinoline-3-carbaldehyde 
• 771555-21-6 2-chloroquinolin-4-ol 
• 1663-67-8 malonoyl dichloride 
• 621-10-3 N,N'-diphenylmalonamide 
• 1613-37-2 Quinoline N-oxide 
• 3039-74-5 4-quinolinol 1-oxide 
• 94298-60-9 4-benzyloxy-quinoline-1-oxide 

Downstream Products

• 4552-42-5 1-(4-chloroquinolin-2-yl)ethan-1-one 
• 870849-89-1 (2-chloro-quinolin-4-yl)-methyl-amine 
• 124466-63-3 (2E,4E) N-Isobutyl 12-(4-chloro-2-quinolinyloxy)-dodeca-2,4-dienamide 
• 341016-12-4 2-chloro-4-morpholin-4-yl-quinoline 
• 80947-25-7 2-chloroquinoline-4-amine 
• 1228173-81-6 2-[(2-benzoyl-4-chlorophenyl)amino]-4-chloroquinoline 
• 1198103-91-1 C₁₉H₁₄ClN 
• 1198103-93-3 C₁₄H₁₁Cl₂N 
• 1198103-88-6 4-chloro-2-(phenylethynyl)quinoline 
• 1198103-92-2 C₁₅H₁₄ClN 
• 1198103-90-0 C₁₈H₁₂ClN 
• 1229434-91-6 H,4ClQuin-BAM 
• 1257940-44-5 C₁₇H₁₃ClN₂O 
• 1257940-48-9 C₂₂H₁₅ClN₂O 

Relevant articles and documents

Coumarin derivative and analogue, preparation method and application thereof

The invention relates to a coumarin derivative and analogue, a preparation method and application thereof, belongs to the field of chemical medicines, and provides a compound shown as a formula I or apharmaceutically acceptable salt thereof, and a preparation method and application of the compound. According to the invention, biological experiments show that the compound has a strong in-vitro anti-fibrosis effect, can obviously reduce deposition of intercellular collagenous fibers on TGF-beta induced NRK-49F cells, and has inhibition on migration of HUVEC cells; and the compound with the structure has a certain curative effect on carbon tetrachloride induced hepatic fibrosis and bleomycin induced pulmonary fibrosis mouse models, is relatively low in toxicity, and provides a new choice forclinical treatment of tissue fibrosis diseases including hepatic fibrosis, pulmonary fibrosis and renal fibrosis.

An efficient click synthesis of chalcones derivatized with two 1-(2-quinolon-4-yl)-1,2,3-triazoles

Chalcones derivatized with 1-(2-quinolonyl)-1,2,3-triazoles were synthesized by reaction of 4-azido-2-quinolones with 1-phenyl-3-(4-propargyloxyphenyl)prop-2-en-1-one, or by aldol reaction of 4-{[1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-1,2,3-triazol-4-yl]methoxy}benzaldehydes with acetophenone. Whereas, chalcones bearing two 1-(2-quinolonyl)-1,2,3-triazoles were synthesized by reaction of 1,3-bis(4-propargyloxyphenyl)prop-2-en-1-one with 4-azido-2-quinolones, or by aldol condensation between 4-{4-[(4-acetylphenoxy)methyl]-1H-1,2,3-triazol-1-yl}quinolin-2(1H)-ones and 4-{[1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-1,2,3-triazol-4-yl]methoxy}benzaldehydes.

Optimization of Orally Bioavailable PI3KδInhibitors and Identification of Vps34 as a Key Selectivity Target

Optimization of a lead series of PI3Kδinhibitors based on a dihydroisobenzofuran core led to the identification of potent, orally bioavailable compound 19. Selectivity profiling of compound 19 showed similar potency for class III PI3K, Vps34, and PI3Kδ, and compound 19 was not well-tolerated in a 7-day rat toxicity study. Structure-based design led to an improvement in selectivity for PI3Kδover Vps34 and, a focus on oral phramacokinetics properties resulted in the discovery of compound 41, which showed improved toxicological outcomes at similar exposure levels to compound 19.