23834-14-2

Basic information

• Product Name: 7-CHLORO-4-HYDRAZINOQUINOLINE
• Synonyms: LABOTEST-BB LT00452674;BUTTPARK 45\09-14;1-(7-CHLORO-4-QUINOLYL)HYDRAZINE;7-CHLORO-4-HYDRAZINOQUINOLINE;TIMTEC-BB SBB000320;7-chloro-4-hydrazino-quinolin;7-chloro-4-quinolylhydrazine;(7-Chloroquinoline-4-yl)hydrazine
• CAS NO: 23834-14-2
• Molecular Formula: C₉H₈ClN₃
• Molecular Weight: 193.63
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinolines;QuinolinesHeterocyclic Building Blocks
• Mol File: 23834-14-2.mol
• Article Data: 24

Chemical Properties

• Melting Point: 219-225 °C (dec.)(lit.)
• Boiling Point: 413.5°Cat760mmHg
• Flash Point: 203.8°C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 4.8E-07mmHg at 25°C
• Refractive Index: 1.758
• PKA: 6.70±0.50(Predicted)
• CAS DataBase Reference: 7-CHLORO-4-HYDRAZINOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-CHLORO-4-HYDRAZINOQUINOLINE(23834-14-2)
• EPA Substance Registry System: 7-CHLORO-4-HYDRAZINOQUINOLINE(23834-14-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: VB2900000
• Hazardous Substances Data: 23834-14-2(Hazardous Substances Data)

Usage

Uses

7-Chloro-4-hydrazinoquinoline was used in the preparation of new Schiff base hydrazone ligand via reaction with o-hydroxybenzaldehyde. It was also used in the preparation of N′-(E)-heteroaromatic-isonicotinohydrazide derivatives and the heteroaromatic 7-chloro-4-quinolinylhydrazone derivatives.

Synthesis

7-chloro-4-hydrazinoquinoline is prepared byhydrazine monohydrate and 4,7-dichloroquinoline in absolute ethanol.Hydrazine monohydrate (2022 mg, 40.0 mmol) and 4,7-dichloroquinoline (800 mg, 4.00 mmol) were dissolved in absolute ethanol (50 ml). The reaction mixture was left under reflux until the reaction has gone to completion and then allowed to cool in the ice bath for crystallization to occur.(676 mg, 87%): mp: 220 – 225 ℃ (Lit.: 223 – 225 ℃); vmax/cm-1 3320 w (N-H), 3050 w (aro. C-H), 1607 m (C=N), 1448 (m, aro. C=C); δH (300 MHz; DMSO-d6) 11.09 (br. s., NH), 8.56-8.40 (2H, m, C(5)H and C(2)H), 7.97 (1H, d, J 1.9, C(8)H), 7.70 (1H, dd, J 9.0, 1.9, C(6)H), 7.10 (1H, d, J 7.2, C(3)H), 5.31 (br. s., NH); δC (75 MHz; DMSO-d6) 155.7 (Ar-C), 142.4 (C(2)H), 138.7 (Ar-C), 137.6 (Ar-C), 126.4 (C(6)H), 125.3 (C(5)H), 119.1 (C(8)H), 113.6 (Ar-C), 98.1 (C(3)H); m/z (-ES) 194 (100%, [M+H]- with 35Cl), 196 (27%, [M+H]- with 37Cl); found by +ES 194.0475, C9H9ClN3 ([M+H]+ with 35Cl), requires 194.0480, error 2.6 ppm.

InChI:InChI=1/C9H8ClN3/c10-6-1-2-7-8(13-11)3-4-12-9(7)5-6/h1-5H,11H2,(H,12,13)

Upstream product

• 86-98-6 4,7-dichloroquinoline 

Downstream Products

• 1251469-31-4 ethyl 1-[(7-chloroquinolin-4-yl)amino]-2-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylate 
• 1251469-33-6 ethyl 1-[(7-chloroquinolin-4-yl)amino]-2-methyl-5-(4-nitrophenyl)-1H-pyrrole-3-carboxylate 
• 1251469-32-5 ethyl 1-[(7-chloroquinolin-4-yl)amino]-2-methyl-5-p-tolyl-1H-pyrrole-3-carboxylate 
• 1251469-30-3 ethyl 1-[(7-chloroquinolin-4-yl)amino]-2-methyl-5-(4-fluorophenyl)-1H-pyrrole-3-carboxylate 

Relevant articles and documents

In silico/in vitro screening and hit evaluation identified new phenothiazine anti-prion derivatives

Prion diseases or transmissible spongiform encephalopathies (TSEs) are a group of rare neurodegenerative disorders. TSEs are characterized by the accumulation of prions (PrPSc) that represent pathological isoforms of the physiological cellular prion protein PrPC. Although the conversion of PrPC to PrPSc is still not completely understood, blocking this process may lead to develop new therapies. Here, we have generated a pharmacophore model, based on anti-prion molecules reported in literature to be effective in phenotypic assay. The model was used to conduct a virtual screen of commercial compound databases that selected a small library of ten compounds. These molecules were then screened in mouse neuroblastoma cell line chronically infected with prions (ScN2a) after excluding neurotoxicity. 1 has been identified as the therapeutic hit on the basis of the following evidence: chronic treatments of ScN2a cells using 1 eliminate PrPSc loaded in both Western blotting analysis and Real-Time Quaking-Induced Conversion (RT-QuIC) assay. We also proposed the mechanism of action of 1 by which it has the ability to bind PrPC and consequentially blocks prion conversion. Herein we describe the results of these efforts.

Antimicrobial activity and spectral, magnetic and thermal studies of some transition metal complexes of a Schiff base hydrazone containing a quinoline moiety

A series of new copper(II), cobalt(II), nickel(II), manganese(II), iron(III), and uranyl(VI) complexes of the Schiff base hydrazone 7-chloro-4-(benzylidenehydrazo) quinoline (HL) were prepared and characterized. The Schiff base behaves as a monobasic bide

4-aminosalicylic acid-based hybrid compounds: Synthesis and in vitro antiplasmodial evaluation

Background: Malaria is a deadly and infectious disease responsible for millions of death worldwide, mostly in the African region. The malaria parasite has developed resistance to the currently used antimalarial drugs, and it has urged researchers to devel

Design, synthesis, antimalarial activity and docking study of 7-chloro-4-(2-(substituted benzylidene)hydrazineyl)quinolines

Background: Malaria is a growing infectious disease burden due to the increasing emergence of resistant strains of Plasmodium falciparum. Because of the limited therapeutic effi-cacy of available antimalarial drugs, the development of potent antimalarial drug agents is there-fore an urgent requirement to fight against resistant malaria. Objective: The objective of this work was to develop novel quinoline-baed antimalarial agents that would be active against resistant P. falciparum malaria. Methods: Some 7-chloro-4-(2-(substituted benzylidene)hydrazineyl)quinolines were synthesized for the evaluation of their potential as possible antimalarial agents, particularly against resistant malaria. The antimalarial activity of synthesized compounds was evaluated in vitro against blood-stage parasites of P. falciparum. Further, molecular docking and drug-likeness including ADMET (Absorption, Distribution, Metabolism, Elimination and Toxicity) studies were also carried out using in silico tools. Results: Results reveal the in vitro antimalarial activity of synthesized 7-chloro-4-(2-(substituted benzylidene)hydrazineyl)quinolines against P. falciparum. The docking study investigates the an-timalarial effectiveness of synthesized quinolines as novel plasmepsin 2 inhibitors. Drug-likeness prediction exhibits acceptable drug-likeness and ADMET properties. Conclusion: Based upon our findings, it is concluded that the molecular scaffold of 7-chloro-4-(2-(substituted benzylidene)hydrazineyl)quinolines may be used as a lead structure for further modi-fications in the search of more potent antimalarial drug molecules.