260430-93-1

Basic information

• Product Name: 6-FLUOROQUINOLINE-2-CARBOXALDEHYDE
• Synonyms: 6-FLUOROQUINOLINE-2-CARBOXALDEHYDE;6-FLUOROQUINOLINE-2-CARBALDEHYDE;6-fluoroquinoline-2-carbaldehyde(SALTDATA: FREE);6-Fluoro-2-quinolinecarboxaldehyde
• CAS NO: 260430-93-1
• Molecular Formula: C₁₀H₆FNO
• Molecular Weight: 175.16
• Mol File: 260430-93-1.mol

Chemical Properties

• Melting Point: 113-120℃
• Boiling Point: 318 °C at 760 mmHg
• Flash Point: 146.1 °C
• Appearance: /Solid
• Density: 1.32 g/cm³
• Vapor Pressure: 0.000372mmHg at 25°C
• Refractive Index: 1.659
• Storage Temp.: 2-8°C
• PKA: 2.98±0.43(Predicted)
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 6-FLUOROQUINOLINE-2-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-FLUOROQUINOLINE-2-CARBOXALDEHYDE(260430-93-1)
• EPA Substance Registry System: 6-FLUOROQUINOLINE-2-CARBOXALDEHYDE(260430-93-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 260430-93-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Fluoroquinoline-2-carboxaldehyde is used as an intermediate in the synthesis of various pharmaceuticals for its important applications in medicinal chemistry. It contributes to the development of new drugs for the treatment of bacterial infections, enhancing the therapeutic options available to combat resistant strains.
Used in Agrochemical Industry:
6-Fluoroquinoline-2-carboxaldehyde is also utilized as an intermediate in the synthesis of agrochemicals, playing a role in the development of new compounds for agricultural applications, such as pesticides or herbicides, to improve crop protection and yield.
Used in Organic Synthesis:
As a versatile building block, 6-Fluoroquinoline-2-carboxaldehyde is used in organic synthesis for the creation of other organic compounds, expanding its applications beyond the pharmaceutical and agrochemical industries into various chemical research areas.

InChI:InChI=1/C10H6FNO/c11-8-2-4-10-7(5-8)1-3-9(6-13)12-10/h1-6H

Upstream product

• 1128-61-6 6-fluoro-2-methyl-quinoline 
• 371-40-4 4-fluoroaniline 
• 15912-68-2 6-fluoro-2-methylquinolin-4-ol 

Downstream Products

• 890840-37-6 C₁₇H₁₅FN₂ 
• 1344654-47-2 tert-butyl {4-[(6-fluoroquinolin-2-yl)methoxyl]phenyl}carbamate 
• 1344654-49-4 4-(6-fluoro-quinolin-2-ylmethoxy)-phenyl amine 
• 1344654-42-7 [4-(6-fluoro-quinolin-2-ylmethoxy)-phenyl]-pyridin-3-ylmethylamine 

Relevant articles and documents

Synthesis and characterization of iron(II) quinaldate complexes

Treatment of iron(II) chloride or iron(II) bromide with 2 equiv of sodium quinaldate (qn=quinaldate or C10H6NO2 -) yields the coordinatively unsaturated mononuclear iron(II) quinaldate complexes Na[FeII(qn)2Cl]-DMF and Na[Fe II(qn)2Br] · DMF (DMF=N,N-dimethylformamide), respectively. When a similar synthesis is carried out using iron(II) triflate, a solvent-derived linear triiron(II) complex, [FeII 3(qn)6(DNF)2], with two five-coordinate iron(II) centers and a single six-coordinate iron(II) center Is obtained. Each of these species has been characterized using X-ray diffraction. The vibrational features of these complexes are consistent with the observed solid-state structures. Each of these compounds exhibits an iron(II)-to-quinaldate (π*) charge-transfer band between 520 and 550 nm. These metalto-ligand charge-transfer bands are sensitive to substitution of the quinaldates as well as alteration of the first coordination sphere ligands. However, the 1H NMR spectra of these paramagnetic high-spin iron(II) complexes are not consistent with retention of the solid-state structures in a DMF solution. The chemical shifts, longitudinal relaxation times (T 1), relative integrations, and substitution of the quinaldate ligands provide a means to fully assign the 1H NMR spectra of the paramagnetic materials. These spectra are consistent with coordination equilibria between five- and sixcoordinate species in a DMF solution. Electrochemical studies are reported to place these oxygen-sensitive compounds in a broader context with other iron(II) compounds. Iron complexes of bidentate quinoline-2-carboxylate-derived ligands are germane to metabolic pathways, environmental remediation, and catalytic applications.

Discovery of novel diarylpyrazolylquinoline derivatives as potent anti-dengue virus agents

A number of diarylpyrazolylquinoline derivatives were synthesized and evaluated for their anti-dengue virus (DENV) activity. Among them, 6-fluoro-2-(1-(4-fluorophenyl)-3- (4-methoxyphenyl)-1H-pyrazol-5-yl)quinoline (11c), 2-[1,3-bis(4-methoxyphenyl)-1H-pyrazol- 5-yl]-6-fluoroquinoline (12c), and 4-[5-(6-fluoroquinolin-2-yl)-3-(4-methoxyphenyl)-1H-pyrazol- 1-yl]benzenesulfonamide (13c) exhibited approximately 10-folds more active anti-DENV-2 activity (IC50 of 1.36, 1.09 and 0.81 μM, respectively) than that of ribavirin (IC50 = 12.61 μM). Compound 13c was also potent inhibited other sero-types of DENV. It reduced DENV replication in both viral protein and mRNA levels, and no significant cell cytotoxicity was detected, with greater than 50% viability of Huh-7-DV-Fluc cells at a concentration of 200 μM. Furthermore, compound 13c can effectively protect mice from DENV infection by reducing disease symptoms and mortality of DENV-infected mice. It represents a potential antiviral agent to block DENV replication in vitro and in vivo. Structural optimization of the initial lead compound, 13c, and the detailed molecular mechanism of action are ongoing.

Visible Light-Driven Decarboxylative Alkylation of Aldehydes via Electron Donor–Acceptor Complexes of Active Esters

There are some synthesis methods from widely available aldehydes to the corresponding ketones, however, they involved in multistep reactions with Grignard’s reagents or transition metal catalysts. In this paper, we have developed photocatalyst-free and visible light-driven decarboxylative alkylation of pyridinaldehydes. The photochemical reactions are initiated via photoinduced single electron transfer from triethylamine to N-hydroxyphthalimide esters in electron donor–acceptor complexes. This photochemical method can achieve to translate 15 pyridinaldehydes and 11 2-quinolinaldehydes to the corresponding ketones. Furthermore, this strategy can also achieve two other transformations, disulfanes to aryl sulfides and a styrene sulfone to the alkyl-substituted alkene.

Iodine-catalyzed oxidative annulation: Facile synthesis of pyrazolooxepinopyrazolones: Via methyl azaarene sp3C-H functionalization

An iodine-catalyzed methyl azaarene sp3 C-H functionalization has been developed for the synthesis of a seven-membered O-heterocyclic architecture containing three different heterocyclic aromatic hydrocarbons. This method can be applied to a wide range of substituted methyl azaarenes and diverse 2,4-dihydro-3H-pyrazol-3-ones, and brings about the efficient preparation of 2,9-dihydrooxepino[2,3-c:6,5-c′]dipyrazol-3(7H)-ones in high yields with the merits of low catalyst loading, good functional group tolerance and metal-free conditions.

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.

Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

An oxidative sp3 C–H bond of methyl-azaheteroarenes protocol was reported for the synthesis of 1,3,4-oxadiazoles via [4 + 1] annulation with hydrazides. This protocol enables 1,3,4-oxadiazole and quinoline linked diheterocycles via selective oxidation of sp3 C–H bond of methyl-azaheteroarenes in the presence of I2-DMSO. The reaction has a broad substrate scope and good functional group tolerance for methyl-azaheteroarenes and hydrazides.

Metal- and radical-free aerobic oxidation of heteroaromatic methanes: An efficient synthesis of heteroaromatic aldehydes

A metal-free and radical-free synthesis of heteroaromatic aldehydes was developed through aerobic oxidation of methyl groups in an I2/DMSO/O2 catalytic system. Under the reaction conditions, various functional groups such as methoxy, aldehyde, ester, nitro, amide, and halo (F, Cl, Br) groups were well tolerated. The bioactive compounds like chlorchinaldin derivative and papaverine were also oxidized to the corresponding aldehydes and ketones. This reaction provided an efficient method for preparing the valuable heteroaromatic aldehydes.

Consecutive Intermolecular Reductive Amination/Asymmetric Hydrogenation: Facile Access to Sterically Tunable Chiral Vicinal Diamines and N-Heterocyclic Carbenes

A highly enantioselective iridium- or ruthenium-catalyzed intermolecular reductive amination/asymmetric hydrogenation relay with 2-quinoline aldehydes and aromatic amines has been developed. A broad range of sterically tunable chiral N,N′-diaryl vicinal diamines were obtained in high yields (up to 95 %) with excellent enantioselectivity (up to >99 % ee). The resulting chiral diamines could be readily transformed into sterically hindered chiral N-heterocyclic carbene (NHC) precursors, which are otherwise difficult to access. The usefulness of this synthetic approach was further demonstrated by the successful application of one of the chiral vicinal diamines and chiral NHC ligands in a transition-metal-catalyzed asymmetric Suzuki–Miyaura cross-coupling reaction and asymmetric ring-opening cross-metathesis, respectively.

Copper-catalyzed three-component reaction of: N-heteroaryl aldehydes, nitriles, and water

An efficient and straightforward method for the synthesis of N-heteroaroyl imides has been successfully developed involving a copper-catalyzed radical-triggered three-component reaction of N-heteroaryl aldehydes, nitriles, and water. Mechanistic studies indicate that the reaction may undergo a radical-triggered Ritter-type reaction in which water serves as the oxygen source for the formation of the C-O bond. The reaction has advantages such as a broad substrate scope for the N-heteroaryl aldehydes, atom economy, and simple operation.