450-95-3

Usage

Uses

Used in Pharmaceutical Industry:
2'-FLUOROACETOPHENONE is used as a synthetic intermediate for the production of -Fluorinated Ketones. These fluorinated compounds are valuable in the development of pharmaceuticals, as they can exhibit improved pharmacokinetic properties, such as increased lipophilicity and metabolic stability, compared to their non-fluorinated counterparts.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2'-FLUOROACETOPHENONE serves as a key building block for the preparation of various organic molecules, including fluorinated derivatives with potential applications in materials science, agrochemistry, and other specialized fields. The unique reactivity of the fluorinated group in 2'-FLUOROACETOPHENONE allows for the development of novel synthetic routes and the creation of new molecular structures with tailored properties.
Used in Method for Synthesizing -Fluorinated Ketone:
2'-FLUOROACETOPHENONE is used as a starting material in the hydrazonation of fatty chain monoketone, a method for synthesizing -Fluorinated Ketones. This process involves the formation of a hydrazone intermediate, which can then be converted to the desired fluorinated ketone product. The use of 2'-FLUOROACETOPHENONE in this method highlights its utility in the synthesis of complex molecular structures with potential applications in various industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 4137, 1954 DOI: 10.1021/ja01645a025Tetrahedron Letters, 28, p. 4733, 1987 DOI: 10.1016/S0040-4039(00)96612-7

InChI:InChI=1/C8H7FO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 3282-32-4 2-diazo-acetophenone 
• 359-06-8 monofluoroacetyl chloride 
• 71-43-2 benzene 
• 530-48-3 1,1-Diphenylethylene 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 
• 459-72-3 ethyl 2-fluoroacetate 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 29114-66-7 1-phenyl-2-fluoropentan-1-one 
• 89263-98-9 difluoro-1,2 phenyl-2 trimethylsilyl ethylene-(Z) 
• 135774-34-4 o-bromo-α-fluoroacetophenone 
• 532-27-4 1-chloroacetophenone 
• 6907-74-0 N-(1-phenylethylidene)-1-propanamine 

Downstream Products

• 337-72-4 2-fluoro-1,1-diphenylethan-1-ol 
• 447-15-4 α-chloro-α-fluoroacetophenone 
• 321-75-5 α-bromo-α-fluorophenylethanone 
• 450-94-2 2-fluoro-1-phenylethanol 
• 403-12-3 2-fluoro-1-(3-nitrophenyl)ethanone 
• 395-17-5 1-fluoro-2-oxo-2-phenyl-ethanesulfonic acid 
• 37032-50-1 Acetic acid (Z)-2-fluoro-3-oxo-3-phenyl-propenyl ester 
• 37032-36-3 2-Fluoro-3-oxo-3-phenyl-propionaldehyde 
• 137586-50-6 4-Fluoro-3-(4-fluoro-phenyl)-2-isobutyryl-5-oxo-5-phenyl-pentanoic acid ethyl ester 
• 124382-14-5 1,1,2-trifluoroethyl phenyl ether 
• 82255-41-2 (R)-(-)-2-fluoro-1-phenylethanol 
• 75600-46-3 1-phenyl-1,1,2-trifluoroethane 
• 98-86-2 acetophenone 
• 450-94-2 (+)-2-fluoro-1-phenylethanol 

Relevant academic research and scientific papers

Monofluoromethylation of tetrahydroisoquinolines by visible-light induced direct C(sp3)-H bond activation

A visible-light photoredox-catalyzed reaction of tetrahydroisoquinolines with β-fluorinated gem-diols results in the formation of C1-monofluoromethylated tetrahydroisoquinolines via C(sp3)-H bond activation. This protocol provides a new method to introduce a CF group with stable, easily-prepared monofluorinated gem-diol as CF source. A mechanistic investigation is presented based on control experiments.

Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles

An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to be a good solvent for this reaction.

Alpha-fluorochalcone derivative and application thereof

The invention provides an alpha-fluorochalcone derivative and application thereof. The derivative comprises pharmaceutically acceptable salt of the derivative. The invention also provides an application of the derivative and the pharmaceutically acceptable salt thereof in preparation of drugs for treating PPAR receptor related diseases. The derivative provided by the invention has the characteristics of good in-vivo absorption, high bioavailability and strong drug effect, thereby having huge clinical application value.

Direct Trifluoromethoxylation without OCF3-Carrier through In Situ Generation of Fluorophosgene

Owing to the high interest in the OCF3 group for pharmaceutical and agrochemical applications, trifluoromethoxylation received great attention in the last years with several new methods for this approach towards OCF3-comprising compounds. Yet, it most often requires the beforehand preparation of specific F3CO? transfer reagents, which can be toxic, expensive, unstable, and/or generate undesired side-products upon consumption. To circumvent this, the in-situ generation of gaseous fluorophosgene from triphosgene, its conversion by fluoride into the OCF3 anion, and the direct use of the latter in nucleophilic substitutions is an appealing strategy, which, although recently approached, has not been fully exploited. We disclose herein our efforts towards this aim.

Synthesis method of alpha or beta-substituted aromatic ketone

The invention discloses a synthesis method of alpha-or beta-substituted aromatic ketone. The method comprises the following steps: under the condition of inert gas, reacting alpha-oxo-aryl ethanone compounds, B2pin2, PDI-CoCl2 and MBHEt3 in an organic solvent at room temperature, then adding a compound 2, and continuously reacting to obtain a compound 3, wherein in the MBHEt3, M is an alkali metal; the compound 2 is selected from the group consisting of deuterated methanol, Selectfluoro, a TogniII reagent or R2CHO; R2 is an aromatic substituent or alkyl; the organic solvent is an aprotic organic solvent. According to the method, the alpha-oxo aryl ethanone is used as a raw material, a cheap and stable boron reagent and an efficient cobalt catalyst which is cheap and easy to obtain are used, an activating reagent MBHEt3 is added to generate an enol boron ether intermediate, then the enol boron ether intermediate and different electrophilic reagents are synthesized into alpha-or beta-substituted aromatic ketone, the reaction is carried out at normal temperature, and the operation is convenient.

Unbalanced-Ion-Pair-Catalyzed Nucleophilic Fluorination Using Potassium Fluoride

An unbalanced ion pair promoter (e.g., tetrabutylammonium sulfate), consisting of a bulky and charge-delocalized cation and a small and charge-localized anion, greatly accelerates nucleophilic fluorinations using easy handling KF. We also successfully converted an inexpensive and commercially available ion-exchange resin to the polymer-supported ion pair promoter (A26–SO42–), which could be reused after filtration. Moreover, A26–SO42– can be used in continuous flow conditions. In our conditions, water is well-tolerated.

Steric-Free Bioorthogonal Labeling of Acetylation Substrates Based on a Fluorine-Thiol Displacement Reaction

We have developed a novel bioorthogonal reaction that can selectively displace fluorine substitutions alpha to amide bonds. This fluorine-thiol displacement reaction (FTDR) allows for fluorinated cofactors or precursors to be utilized as chemical reporters, hijacking acetyltransferase-mediated acetylation both in vitro and in live cells, which cannot be achieved with azide- or alkyne-based chemical reporters. The fluoroacetamide labels can be further converted to biotin or fluorophore tags using FTDR, enabling the general detection and imaging of acetyl substrates. This strategy may lead to a steric-free labeling platform for substrate proteins, expanding our chemical toolbox for functional annotation of post-translational modifications in a systematic manner.

LINKING AMINO ACID SEQUENCES, MANUFACTURING METHOD THEREOF, AND USE THEREOF

This invention provides compositions comprising linked amino acid sequences, pharmaceutical compositions comprising linked amino acid sequences, and methods of making thereof. This invention also provides methods of delivering said compositions to subjects and methods of treating various disorders and diseases using the said compositions.

Method for synthesizing alpha-fluorinated ketone through hydrazone aliphatic chain monoketone

The invention belongs to the technical field of organic synthesis, and provides a method for synthesizing alpha-ketone fluoride through hydrazone aliphatic chain monoketone, which comprises the following steps of: reacting aliphatic chain monoketone with hydrazine hydrate to obtain hydrazone, and reacting hydrazone with a compound represented by formula 2 under a heating condition to complete hydrazone defluorination. The fluorinated product is widely applied to medicines, the reaction conditions are mild, and the process is simple.

Double Enzyme-Catalyzed One-Pot Synthesis of Enantiocomplementary Vicinal Fluoro Alcohols

A double-enzyme-catalyzed strategy for the synthesis of enantiocomplementary vicinal fluoro alcohols through a one-pot, three-step process including lipase-catalyzed hydrolysis, spontaneous decarboxylative fluorination, and subsequent ketoreductase-catalyzed reduction was developed. With this approach, β-ketonic esters were converted to the corresponding vicinal fluoro alcohols with high isolated yields (up to 92percent) and stereoselectivities (up to 99percent). This new cascade process addresses some issues in comparison with traditional methods such as environmentally hazardous reaction conditions and low stereoselectivity outcome.