21597-61-5

Usage

Uses

Used in Organic Synthesis:
3-Fluoro-naphthalene-2-carboxaldehyde is used as a reagent for the catalytic nucleophilic addition to aromatic carbonyl compounds. Its electron-withdrawing fluorine atom activates the aromatic ring, facilitating the addition of nucleophiles to the carbonyl group. This property makes it a valuable intermediate in the synthesis of various complex organic molecules and pharmaceuticals.
Used in the Production of Fluorinated Compounds:
Due to the presence of the fluorine atom, 3-Fluoro-naphthalene-2-carboxaldehyde can be used as a starting material for the synthesis of other fluorinated naphthalene derivatives. Fluorinated compounds often exhibit unique chemical and physical properties, such as increased lipophilicity and metabolic stability, which can be advantageous in various applications, including drug development and materials science.
Used in the Synthesis of Heterocyclic Compounds:
The reactivity of the aldehyde group in 3-Fluoro-naphthalene-2-carboxaldehyde allows it to participate in various condensation and cyclization reactions, leading to the formation of heterocyclic compounds. These heterocyclic compounds can have diverse applications, such as in pharmaceuticals, agrochemicals, and as functional materials.
Used in the Development of Catalysts and Ligands:
The combination of the fluorine atom and the aldehyde group in 3-Fluoro-naphthalene-2-carboxaldehyde can be exploited in the design of catalysts and ligands for asymmetric synthesis and other enantioselective reactions. The electron-withdrawing effect of the fluorine atom can influence the reactivity and selectivity of the catalyst or ligand, leading to improved synthetic methods and processes.

Upstream product

• 1718-17-8 2-carbomethoxy-3-fluoronaphthalene 
• 323-09-1 2-fluoronaphthalene 
• 68-12-2 N,N-dimethyl-formamide 
• 21597-54-6 Methyl 3-amino-2-naphthoate 
• 5959-52-4 2-Amino-3-naphthoic acid 
• 66-99-9 β-naphthaldehyde 

Downstream Products

• 34280-38-1 trans-1-(2-Fluor-3-naphthyl)-2-phenylaethylen 
• 1373121-92-6 N-(4-chlorophenyl)-3-fluoro-N'-hydroxy-2-naphthimidamide 
• 1373121-85-7 N-(4-chlorophenyl)naphtho[2,3-d]isoxazol-3-amine 

Relevant academic research and scientific papers

Intermolecular Dearomatization of Naphthalene Derivatives by Photoredox-Catalyzed 1,2-Hydroalkylation

An intermolecular hydroalkylative dearomatization of naphthalenes with commercially available α-amino acids is achieved via visible-light photoredox catalysis. With an organic photocatalyst, a series of multi-substituted 1,2-dihydronaphthalenes are obtained in good-to-excellent yields. Intriguingly, by tuning the substituents at the C2 position of naphthalenes, formal dearomative [3+2] cycloadditions occur exclusively via a hydroalkylative dearomatization–cyclization sequence. This overall redox-neutral method features mild reaction conditions, good tolerance of functionalities, and operational simplicity. Diverse downstream elaborations of the products are demonstrated. Preliminary mechanistic studies suggest the involvement of a radical–radical coupling pathway.

Design, synthesis, and biological evaluation of conformationally constrained analogues of naphthol AS-E as inhibitors of CREB-mediated gene transcription

Cyclic AMP response element binding protein (CREB) is often dysregulated in cancer cells and is an attractive cancer drug target. Previously, we described naphthol AS-E (1) as a small molecule inhibitor of CREB-mediated gene transcription. To understand its bioactive conformation, a series of conformationally constrained analogues of 1 were designed and synthesized. Biological evaluation of these analogues suggests that the global energy minimum of 1 is the likely bioactive conformation.

1H and 13C NMR assignments of all three isomeric o-fluoronaphthaldehydes and three o-fluorophenanthrene aldehydes

Three isomeric o-fluoronaphthaldehydes, 9-fluorophenanthrene, and three previously unreported o-fluorophenanthrene aldehydes were analyzed in detail by multiple NMR techniques to provide unambiguous assignment of structures and resonances. The six aldehyd

SYNTHESIS OF MONOFLUOROBENZOPHENANTHRENES

Synthesis of 1-, 2-, 3- and 4-fluorobenzophenanthrenes by photocyclization of appropriate β-naphth-1-yl fluorostyrene is described.An improved synthesis of 6-fluorobenzophenanthrene was developed.Partial photochemical debromination occured upon cycl