14510-06-6

Usage

Uses

Used in Chemical Synthesis:
8-Hydroxyquinoline-2-carboxaldehyde is used as a key intermediate in the synthesis of various organic compounds for different applications. It serves as a building block for the creation of complex molecules with specific properties and functions.
Used in Pharmaceutical Industry:
8-Hydroxyquinoline-2-carboxaldehyde is used as a starting material for the development of new pharmaceutical compounds. Its unique chemical structure allows for the formation of various derivatives with potential therapeutic applications.
Used in Material Science:
In the field of material science, 8-Hydroxyquinoline-2-carboxaldehyde is used as a component in the development of advanced materials with specific properties, such as optical, electronic, or magnetic characteristics.
Used in Analytical Chemistry:
8-Hydroxyquinoline-2-carboxaldehyde is employed as a reagent in analytical chemistry for the detection and quantification of various metal ions, particularly due to its ability to form stable complexes with these ions.
Used in the Preparation of Schiff Bases:
8-Hydroxyquinoline-2-carboxaldehyde is used as a reactant in the preparation of Schiff bases, which are important in the synthesis of various organic compounds and have applications in coordination chemistry and medicinal chemistry.
Used in the Synthesis of 8-Hydroxy-2-Quinoline-1-Aminopyrene:
8-Hydroxyquinoline-2-carboxaldehyde is used as a reactant in the synthesis of 8-hydroxy-2-quinoline-1-aminopyrene through a Schiff-base reaction with 1-aminopyrene. 8-Hydroxyquinoline-2-carboxaldehyde may have potential applications in various fields, such as pharmaceuticals or materials science.
Used in the Synthesis of (E)-2-((2-(Pyridin-2-yl)hydrazono)methyl)quinolin-8-ol:
8-Hydroxyquinoline-2-carboxaldehyde is used as a starting material in the synthesis of (E)-2-((2-(pyridin-2-yl)hydrazono)methyl)quinolin-8-ol by coupling with 2-hydrazinopyridine. 8-Hydroxyquinoline-2-carboxaldehyde may have potential applications in various fields, such as pharmaceuticals or materials science.
Used in the Synthesis of 8-Hydroxyquinoline-2-Carbaldehyde Oxime:
8-Hydroxyquinoline-2-carboxaldehyde is used as a reactant in the synthesis of 8-hydroxyquinoline-2-carbaldehyde oxime. This derivative may have potential applications in various fields, such as pharmaceuticals or materials science.
Used in the Synthesis of 2-[(8-Hydroxyquinoline)-2-methylaminoethyl]-β-D-glucopyranoside:
8-Hydroxyquinoline-2-carboxaldehyde is used as a starting material in the synthesis of 2-[(8-hydroxyquinoline)-2-methylaminoethyl]-β-D-glucopyranoside. 8-Hydroxyquinoline-2-carboxaldehyde may have potential applications in the pharmaceutical industry, particularly in the development of new drugs with specific therapeutic properties.

InChI:InChI=1/C10H7NO2/c12-6-8-5-4-7-2-1-3-9(13)10(7)11-8/h1-6,13H

Upstream product

• 826-81-3 2-methyl-8-quinolinol 
• 148-24-3 8-quinolinol 
• 93315-49-2 2-methyl-8-(benzyloxy)quinoline 
• 88238-73-7 8-benzyloxyquinolin-2-yl-carboxaldehyde 
• 27037-61-2 2‐methyl‐8‐acetoxyquinoline 
• 1070896-53-5 2-quinolinecarboxaldehyde, 8-[[(1,1-dimethylethyl)dimethylsilyl]oxy] 
• 171735-72-1 8-tert-butyldimethylsilyloxy-2-methyl-quinoline 
• 123-91-1 1,4-dioxane 

Downstream Products

• 91575-51-8 2-vinyl-8-quinolinol 
• 343372-33-8 7,13-bis(8-hydroxyquinolin-2-ylmethyl)-7,13-diaza-4,10,16-trithia-1-oxacyclooctadecane 
• 5548-72-1 N-(8-hydroxyl-2-quinolylmethylene)-o-aminophenol 
• 442555-76-2 2-[2-(4-nitrophenyl)ethenyl]quinolin-8-ol 
• 1289642-90-5 2-((2,6-difluorophenylimino)methyl)quinolin-8-ol 

Relevant academic research and scientific papers

A novel cysteine fluorescent probe based on benzothiazole and quinoline with a large stokes shift and application in living cell and mice

A novel fluorescent probe based on hydroxyquinoline conjugated with benzothiazolyl unit dye Doc-Ac was prepared. The results of fluorescent and absorption spectroscopic responses towards amino acids showed that the probe had a capability of rapidly and selectively detecting cysteine over other amino acids with a large stokes shift in aqueous solution. The sensing mechanism was proved by the proton NMR and high resolution mass spectrometry analysis. The fluorescence images indicated that this probe could discriminate the exogenous/endogenous cysteine in living cells and mice.

Cu2+-selective colorimetric signaling by sequential hydrolysis and oxidative coupling of a Schiff base

A new Cu2+-selective probe was developed based on the Cu2+-induced sequential hydrolysis and oxidative coupling reactions of 4-aminoantipyrine-appended 8-hydroxyquinoline derivative 1. Cu2+-assisted hydrolysis of the enamine moiety of Schiff base 1 afforded its constituents, 4-aminoantipyrine and 8-hydroxyquinoline-2-carboxaldehyde. The Cu2+-induced oxidative coupling between these in situ generated compounds afforded a quinoneimine dye. Prominent naked-eye-detectable selective signaling of Cu2+ions, assisted by EDTA, was realized through a color change from faint yellow to pink with a detection limit of 1.81 × 10?6M.

Rhombus-shaped tetranuclear [Ln4] complexes [Ln = Dy(III) and Ho(III)]: Synthesis, structure, and SMM behavior

The reaction of a new hexadentate Schiff base hydrazide ligand (LH 3) with rare earth(III) chloride salts in the presence of triethylamine as the base afforded two planar tetranuclear neutral complexes: [{(LH)2Dy4}(μ2

Synthesis and characterization of quinoline-carbaldehyde derivatives as novel inhibitors for leishmanial methionine aminopeptidase 1

Methionine aminopeptidase 1 of Leishmania donovani (LdMetAP1) is a novel antileishmanial target for its role in vital N-terminal methionine processing. After LdMetAP1 expression and purification, we employed a series of biochemical assays to determine opt

Novel lavendamycin analogues as antitumor agents: Synthesis, in vitro cytotoxicity, structure-metabolism, and computational molecular modeling studies with NAD(P)H:quinone oxidoreductase 1

Novel lavendamycin analogues with various substituents were synthesized and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor agents. Pictet-Spengler condensation of quinoline- or quninoline-5,8-dione aldehydes with tryptamin

Base- and Metal-Dependent Self-Assembly of Lathanide-Organic Coordination Polymers or Macrocycles with Tetradentate Acylhydrazone-based Ditopic Ligands

Herein, we report a comprehensive study on the lanthanide-directed coordination self-assembly with two bis-tetradentate acylhydrazone ligands H4L1 and H4L2. Multifarious outcomes, which are base- and metal-dependent, were revealed by NMR, ESI-TOF-MS and X-ray crystallography. In the absence of base, bent H4L1 was assembled into dinuclear double-strand helicate Ln2(H2L1)2 by partially-deprotonated assembly with La, Sm or Eu, while trinuclear Ln3(H2L1)3 with Yb or Lu. For linear H4L2, infinite 1D zig-zag metal-organic polymeric chain (Ln2H2L2)n was obtained. However, complete deprotonated L1 and L2 assembled into discrete trinuclear Ln3(L1/2)3 and tetranuclear Ln4(L1/2)4 macrocyclic structures under the basic condition. For these, there are multiple possible isomers coexisting in the solution which were enumerated and simulated with molecular mechanic modeling. Visible-light sensitized NIR emissions on the Yb complexes have been observed, endowing them potential application in photofunctional materials.

Synthesis and biological evaluation of novel 8-substituted quinoline-2-carboxamides as carbonic anhydrase inhibitors

A series of novel 8-substituted-N-(4-sulfamoylphenyl)quinoline-2-carboxamides was synthesised by the reaction of 8-hydroxy-N-(4-sulfamoylphenyl) quinoline-2-carboxamide with alkyl and benzyl halides. The compounds were assayed for carbonic anhydrase (CA)

A rhodamine derivative for Hg2+-selective colorimetric and fluorescent sensing and its application to in vivo imaging

A rhodamine-based sensor has been developed for the detection of mercuric ions. The colorimetric and fluorescence responses, allowing naked-eye detections, are based on Hg2+-induced opening of the rhodamine spirocycle. Among all the testes ions, only Hg2+ generated a significant fluorescence enhancement of up to 300-fold, with a bright yellow-green emission. This sensor was a low toxic compound, and was successfully applied in the in vivo imaging of Hg2+ in Spill 2 cells and C. elegans. This approach provides a sensitive and accurate method for the estimation of Hg2+ in environmental, tobacco and biological applications.

Linear and nonlinear optical properties of Ln-Zn heteronuclear complexes from a Schiff base ligand containing 8-hydroxyquinoline moiety

Starting from a Schiff base ligand containing 8-hydroxyquinoline moiety, namely, 3,3′-(1E,1′E)-(propane-1,3-diylbis(azan-1-yl-1-ylidene)) bis(methan-1-yl-1-ylidene) diquinolin-8-ol (H2PBIQ), five heteronuclear Ln(III)-Zn(II) complexes (([Eu2Zn(PBIQ) 2(NO3)4]·CH2Cl2, 1), ([Tb2Zn(PBIQ)2(NO3)4] ·CH2Cl2, 2), ([Gd2Zn(PBIQ) 2(NO3)4]·CH2Cl2, 3), ([Nd2Zn(PBIQ)2(NO3)4] ·CH2Cl2, 4)), and ([Yb2Zn(PBIQ) 2(NO3)4]·CH2Cl2, 5) were obtained. Due to the low energy level resided in the excited state, the Schiff base ligand can sensitize near infrared emitting Ln(III) ions (Nd and Yb), while visible light emitting Eu and Tb ions cannot be excited. Instead, nonlinear optical properties were observed in Eu/Tb-Zn heteronuclear complexes.

A novel fluorescent chemosensor based on coumarin and quinolinyl-benzothiazole for sequential recognition of Cu2+ and PPi and its applicability in live cell imaging

In this study, a highly selective fluorescent sensor (E)-2-((2-(benzo[d]thiazol-2-yl)quinolin-8-yl)oxy)-N′-((7-(diethylamino)-2-oxo-2H-chromen-3-yl)methylene)acetohydrazide (TQC) was synthesized from 2-methylquinolin-8-ol and 4-(diethylamino)-2-hydroxybenzaldehyde and its structure was characterized by 1H NMR, 13C NMR, ESI-HR-MS and density functional theory (DFT) calculation. Sensor TQC showed an obvious “on-off-on” fluorescence response to Cu2+ and PPi in a DMSO/HEPES (3:2 v/v, pH = 7.4) buffer system. The detection limits of sensor TQC were 0.06 μM to Cu2+ and 0.01 μM to PPi. In addition, sensor TQC showed a 1:1 binding stoichiometry to Cu2+ and TQC-Cu2+ complex showed a 2:1 binding stoichiometry to PPi. The optimum pH range of sensor TQC and TQC-Cu2+ was 3–8. Further studies demonstrated that sensor TQC could be made into test paper strips for the qualitative of Cu2+ and PPi and showed sequentially “on-off-on” fluorescent bio-imaging of Cu2+ and PPi in HeLa cells.