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Usage

Uses

Used in Pharmaceutical Industry:
6-Fluoro-1-tetralone is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to enhance the properties of the final drug products. Its unique structure allows for the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
6-Fluoro-1-tetralone is used as a building block in the production of agrochemicals, such as pesticides and herbicides, to improve their performance and selectivity in controlling pests and weeds.
Used in Organic Synthesis:
6-Fluoro-1-tetralone is utilized as a valuable intermediate in organic synthesis for the preparation of a wide range of organic compounds, including fine chemicals, specialty chemicals, and advanced materials. Its presence in the molecule can influence the reactivity, stability, and properties of the synthesized compounds.

InChI:InChI=1/C10H9FO/c11-8-4-5-9-7(6-8)2-1-3-10(9)12/h4-6H,1-3H2

Upstream product

• 70631-88-8 4-(3-fluorophenyl)butanoic acid 
• 339365-53-6 1-(4-fluorophenyl)cyclobutan-1-ol 
• 589-06-0 4-(4-fluorophenyl)butanoic acid 
• 127404-66-4 4-(4-fluorophenyl)but-3-enoic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 456-48-4 3-Fluorobenzaldehyde 
• 149437-76-3 5-(4-fluorophenyl)-5-oxopentanoic acid 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 3470-46-0 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid 
• 455-36-7 1-(3-fluorophenyl)ethanone 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 3470-53-9 6-amino-1-tetralone 
• 3470-50-6 6-Hydroxy-1-tetralone 
• 62942-25-0 (3-fluorophenyl)tri-n-butyltin 

Downstream Products

• 53842-01-6 7-fluoro-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one 
• 149915-80-0 6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 782427-32-1 6-fluoro-tetrahydronaphthalen-2-amine 
• 1231765-07-3 6-(3-Fluoro-phenylsulfanyl)-3,4-dihydro-2H-naphthalen-1-one 
• 1350662-98-4 ethyl 6-fluoro-1-hydroxy-2-naphthoate 
• 1422684-05-6 (E)-6-fluoro-N-(4-fluorophenyl)-2-(((4-fluorophenyl)imino)methyl)-3,4-dihydronaphthalen-1-amine 
• 1422684-07-8 (E)-6-fluoro-N-(4-methoxyphenyl)-2-(((4-methoxyphenyl)imino)methyl)-3,4-dihydronaphthalen-1-amine 
• 1422684-08-9 (E)-6-fluoro-N-(4-nitrophenyl)-2-(((4-nitrophenyl)imino)methyl)-3,4-dihydronaphthalen-1-amine 
• 885269-59-0 6-fluoro-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid 

Relevant academic research and scientific papers

Radical Decarboxylative Carbometalation of Benzoic Acids: A Solution to Aromatic Decarboxylative Fluorination

Abundant aromatic carboxylic acids exist in great structural diversity from nature and synthesis. To date, the synthetically valuable decarboxylative functionalization of benzoic acids is realized mainly by transition-metal-catalyzed decarboxylative cross couplings. However, the high activation barrier for thermal decarboxylative carbometalation that often requires 140 °C reaction temperature limits both the substrate scope as well as the scope of suitable reactions that can sustain such conditions. Numerous reactions, for example, decarboxylative fluorination that is well developed for aliphatic carboxylic acids, are out of reach for the aromatic counterparts with current reaction chemistry. Here, we report a conceptually different approach through a low-barrier photoinduced ligand to metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation strategy, which generates a putative high-valent arylcopper(III) complex, from which versatile facile reductive eliminations can occur. We demonstrate the suitability of our new approach to address previously unrealized general decarboxylative fluorination of benzoic acids.

Regioselective Electrochemical Cyclobutanol Ring Expansion to 1-Tetralones

A mild electrochemical method for the regioselective preparation of 1-tetralones under environmentally friendly conditions from readily available cyclobutanols was developed. A series of aromatic- and heteroaromatic-fused 1-tetralones was accessed through ring expansion of the functionalized cyclobutanols via electrochemical generation of alkoxy radicals and intramolecular cyclization.

Radical-Polar Crossover Annulation: A Platform for Accessing Polycyclic Cyclopropanes

Photoredox-mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are noto

Synthesis of Novel Pterocarpen Analogues via [3?+?2] Coupling-Elimination Cascade of α,α-Dicyanoolefins with Quinone Monoimines

By employing triethylamine as a catalyst, [3?+?2] coupling-elimination cascade of α,α-dicyanoolefins with quinone monoimines was realized. The reactions afforded various novel pterocarpen analogues with generally moderate yields (up to 75%). In addition, a plausible reaction mechanism was proposed.

Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light

An intramolecular arene alkylation reaction has been developed using the organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors. Reaction conditions were optimized via high-throughput experimentation, and electron-rich and electron-deficient arenes and heteroarenes are viable reaction substrates. This reaction enables access to a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.

Design, synthesis and evaluation of novel N-phenylbutanamide derivatives as KCNQ openers for the treatment of epilepsy

KCNQ (Kv7) has emerged as a validated target for the development of novel anti-epileptic drugs. In this paper, a series of novel N-phenylbutanamide derivatives were designed, synthesized and evaluated as KCNQ openers for the treatment of epilepsy. These compounds were evaluated for their KCNQ opening activity in vitro and in vivo. Several compounds were found to be potent KCNQ openers. Compound 1 with favorable in vitro activity was submitted to evaluation in vivo. Results showed that compound 1 owned significant anti-convulsant activity with no adverse effects. It was also found to posses favorable pharmacokinetic profiles in rat. This research may provide novel potent compounds for the discovery of KCNQ openers in treating epilepsy.

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion

A regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion is described. A variety of 1-tetralones are furnished under mild reaction conditions from tertiary cyclobutanols regardless of the electronic properties and steric hindrance of substituents, providing a new and practical method to access diverse 1-tetralone building blocks. Preliminary experimental and DFT studies revealed that a radical-mediated sequence of C-C bond cleavage/C-C bond formation is involved.

Design, synthesis, structure, and dehydrogenation reactivity of a water soluble o-iodoxybenzoic acid derivative bearing a trimethylammonium group

5-Trimethylammonio-1, 3-dioxo-1, 3-dihydro-1λ5-benzo[d][1, 2]iodoxol-1-ol anion (AIBX 1a), an o-iodoxybenzoic acid (IBX) derivative having the trimethylammonium moiety on its phenyl ring, possesses very good solubility in water and distinct oxidative properties from IBX, which is demonstrated in the oxidation of various β-keto esters to the corresponding dehydrogenated products using water as cosolvent. The regeneration of AIBX 1a can be easily realized from the reaction mixture due to its good water solubility.2011 American Chemical Society.