5470-96-2

Basic information

• Product Name: 2-Quinolinecarboxaldehyde
• Synonyms: QUINOLINE-2-CARBALDEHYDE;QUINOLINE-2-CARBOXALDEHYDE;TIMTEC-BB SBB004007;2-FORMYLQUINOLINE;2-QUINOLINECARBALDEHYDE;2-QUINOLINECARBOXALDEHYDE;Quinaldehyde;Quinoline-2-carboxaldehyde,98%
• CAS NO: 5470-96-2
• Molecular Formula: C10H7NO
• Molecular Weight: 157.17
• EINECS: 226-804-3
• Product Categories: Quinoline&Isoquinoline;Quinoline Derivertives;Quinolinecarboxylic Acids, etc.;Quinolines;Quinoline;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 5470-96-2.mol

Chemical Properties

• Melting Point: 70-72 °C(lit.)
• Boiling Point: 314.3 °C at 760 mmHg
• Flash Point: 151.9 °C
• Appearance: Orange to brown/Crystals or Crystalline Powder
• Density: 1.223 g/cm³
• Vapor Pressure: 0.00047mmHg at 25°C
• Refractive Index: 1.687
• Storage Temp.: Refrigerator (+4°C)
• PKA: 3.74±0.40(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 113061
• CAS DataBase Reference: 2-Quinolinecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Quinolinecarboxaldehyde(5470-96-2)
• EPA Substance Registry System: 2-Quinolinecarboxaldehyde(5470-96-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 5470-96-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Quinolinecarboxaldehyde is used as a key intermediate in the synthesis of various organic compounds. It is particularly useful in the preparation of 3-(2-quinolyl)-1-phenyl-2-propenone through rapid, tandem aldol-Michael reactions with the lithium, sodium, and potassium enolates of acetophenone. This application is significant in the development of new chemical compounds and materials.
Used in Coordination Chemistry:
In coordination chemistry, 2-Quinolinecarboxaldehyde is used to synthesize imine-type ligands. These ligands are essential in the formation of metal complexes, which have a wide range of applications, including catalysis, sensing, and pharmaceuticals.
Used in Environmental Science:
2-Quinolinecarboxaldehyde is also used in the development of sugar-quinoline fluorescent sensors for the detection of Hg2+ ions in natural water. This application is crucial for environmental monitoring and ensuring the safety of water resources.

Purification Methods

Distil it in steam and recrystallise it from H2O. Protect it from light. The semicarbazone has m 254o (from aqueous EtOH), and the picrate has m 197-199o. [Beilstein 21 H 322, 21 III/IV 4034, 21/8 V 442.]

InChI:InChI=1/C10H7NO/c12-7-9-6-5-8-3-1-2-4-10(8)11-9/h1-7H

Upstream product

• 81124-50-7 (E)-3-(2-quinolinyl)-2-propenoic acid 
• 110-88-3 1,3,5-Trioxan 
• 91-22-5 quinoline 
• 4377-41-7 2-Chloromethylquinoline 
• 79-46-9 2-nitropropane 
• 53867-81-5 2-(dibromomethyl)quinoline 
• 67-56-1 methanol 
• 5662-03-3 2-(1H-quinolin-2-ylidene)-indan-1,3-dione 
• 91-63-4 2-methylquinoline 
• 1335204-96-0 quinolin-2-yl(butylamino)methyldiphenylphosphine oxide 
• 607-67-0 4-hydroxy-2-methylquinoline 
• 50488-44-3 4-Bromo-2-methylquinoline 
• 2005-43-8 2-bromoquinoline 
• 113726-29-7 tert-butyl(quinolin-2-ylmethylene)amine 

Downstream Products

• 14148-37-9 Chinolin-2-aldehyd-2,4-dinitrophenylhydrazon 
• 95705-00-3 2-(1,3-diphenyl-imidazolidin-2-yl)-quinoline 
• 4401-04-1 (E)-1-(4-methoxyphenyl)-3-(quinolin-2-yl)prop-2-en-1-one 
• 3678-74-8 2-(Diphenylmethyl)quinoline 
• 18831-34-0 4,4'-(quinolin-2-yl-methanediyl)-bis-phenol 
• 1780-17-2 quinolin-2-ylmethanol 
• 93-10-7 quinoline-2-carboxylic acid 
• 7463-70-9 2-quinolinecarboxaldehyde hydrazone 
• 3561-22-6 1,2-di(quinolyl-2)-1,2-ethanedione 
• 5749-82-6 2-hydroxy-1,2-di-quinolin-2-yl-ethanone 
• 51265-25-9 4-phenyl-2,2′-biquinoline 
• 66155-11-1 1-(5-bromo-2-hydroxy-phenyl)-3-quinolin-2-yl-propenone 
• 220854-77-3 (Z)-2-Benzyloxycarbonylamino-3-quinolin-2-yl-acrylic acid methyl ester 

Relevant articles and documents

STIMULI - OR BIO- RESPONSIVE COPOLYMERS, THE POLYMERSOMES COMPRISING THE SAME AND THEIR USE IN DRUG DELIVERY

The present invention concerns amphiphilic copolymers that may be photo- or redox-cleavable and that may assemble into polymersomes. It also concerns their process of preparation and their use as drug carriers.

A Metal- and Azide-free Oxidative Coupling Reaction for the Synthesis of [1,2,3]Triazolo[1,5-a]quinolines and their Application to Construct C?C and C-P Bonds, 2-Cyclopropylquinolines and Imidazo[1,5-a]quinolines

An iodine-promoted one-pot cascade oxidative annulation reaction has been developed for the synthesis of [1,2,3]triazolo[1,5-a]quinolines from methyl azaarenes and N-tosylhydrazines. The reaction has a broad substrate scope and can be easily scaled up to gram-scale. 1,2,3-Triazoles are an important skeletal structure for the construction of C?C and C?P bonds, 2-cyclopropylquinolines and imidazo[1,5-a]quinolines, for which different synthetic applications were explored. (Figure presented.).

Iodine-Catalyzed Construction of Dihydrooxepines via 3-Methyl-5-Pyrazolones C?H Oxidation/Functionalization of Quinolines Cascade

An efficient iodine-catalyzed [3+3+1] annulation for the construction of dihydrooxepine scaffolds with quinoline units was developed. This strategy involves a seven-membered dihydrooxepine with a broad substrate scope through a formal three-component tandem reaction. Further derivation of the target product produced a trioxabicycle scaffold, which formed the basic core of natural products and pharmaceutical molecules.

Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls

An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.

Design, synthesis and biological evaluation of novel thiohydantoin derivatives as potent androgen receptor antagonists for the treatment of prostate cancer

Prostate cancer (PC) is the most common malignancy in men worldwide. Here, two series of novel thiohydantoin derivatives of enzalutamide as potent androgen receptor (AR) antagonists were designed and synthesized. Among them, compound 31c was identified as an AR antagonist which is 2.3–fold more potent than enzalutamide. Molecular docking studies were performed to explain the improved potency of 31c at AR. In cell proliferation assays, 31c exhibited similar anti-proliferative activities with enzalutamide against hormone sensitive LNCaP cells and AR-overexpressing LNCaP/AR cells. These data indicate that 31c can be a good lead compound for further structure optimization for the treatment of prostate cancer.

Rh-Catalyzed Formal [3+2] Cyclization for the Synthesis of 5-Aryl-2-(quinolin-2-yl)oxazoles and Its Applications in Metal Ions Probes

A facile and efficient strategy for the synthesis of 5-aryl-2-(quinolin-2-yl)oxazoles via rhodium-catalyzed formal [3+2] cyclization of 4-aryl-1-tosyl-1H-1,2,3-triazoles with quinoline-2-carbaldehydes has been described. The protocol employs mild conditions and offers good yields of diverse 2,5-aryloxazole derivatives with a broad reaction scope. It is amenable to gram-scale synthesis and easily transformation. Moreover, this 5-aryl-2-(quinolin-2-yl)oxazole skeleton is indeed a new fluorophore and its applications in metal ions probes are also investigated and showed fluorescent responses to mercury ion.

Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.

Iodine-Promoted Synthesis of Dipyrazolo/Diuracil-Fused Pyridines and o-Amino Diheteroaryl ketones via Oxidative Domino Annulation of 2/4-Methylazaarenes

The iodine-promoted oxidative domino annulation and carbonylation process has been developed for the synthesis of biologically important azaarene-substituted bis-pyrazolo[3,4-b:4′,3′-e]pyridines (BPPs), diuracilpyridines and o-amino diheteroaryl ketones. The domino procedure proceeded with easily available methyl azaarenes, 5-aminouracils and substituted 5-aminopyrazoles. This protocol is a simple and metal-free approach which exhibits high functional group compatibility and broad substrates scope. Moreover, this transformation can be applied for the preparation of dipyrazolo/diuracil-fused pyridines on a gram scale. (Figure presented.).

Methanol as a formylating agent in nitrogen heterocycles

A radical mediated C-H direct formylation of N-heteroarenes with methanol is reported. The reaction features a novel iron-catalyzed Minisci oxidative coupling process using commercially available methanol as a formylating reagent. It effectively solved the long-standing problems associated with using methanol as a formylating reagent in these types of reactions. Compared to the traditional Minisci C-H formylation methods, this protocol is highly atom-economical, simple to operate, and environmentally friendly and shows good functional group tolerance. This Minisci formylation strategy is a straightforward approach for the late-stage functionalization of N-heteroarenes. This journal is

Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics

Nicotinamide N-methyltransferase (NNMT) methylates nicotinamide (vitamin B3) to generate 1-methylnicotinamide (MNA). NNMT overexpression has been linked to a variety of diseases, most prominently human cancers, indicating its potential as a therapeutic target. The development of small-molecule NNMT inhibitors has gained interest in recent years, with the most potent inhibitors sharing structural features based on elements of the nicotinamide substrate and the S-adenosyl-l-methionine (SAM) cofactor. We here report the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary analytical techniques, modeling studies, and cell-based assays provide insights into the binding mode, affinity, and selectivity of these inhibitors.