21120-36-5

Basic information

• Product Name: 2'-FLUOROPROPIOPHENONE
• Synonyms: (R,S)-2-Fluoro-1-phenyl-propan-1-one;R,S-2-Fluoro-1-phenyl-propan-1-one;1-(2-FLUOROPHENYL)PROPAN-1-ONE;ETHYL 2-FLUOROPHENYL KETONE;1-Propanone, 2-fluoro-1-phenyl- (9CI);2-Fluoro-1-phenyl-1-propanone;α-Fluoropropiophenone;Einecs 244-220-7
• CAS NO: 21120-36-5
• Molecular Formula: C₉H₉FO
• Molecular Weight: 152.17
• EINECS: 244-220-7
• Product Categories: ACETYLHALIDE
• Mol File: 21120-36-5.mol

Chemical Properties

• Boiling Point: 95-99 °C19 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: /
• Density: 1.102 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5043(lit.)
• CAS DataBase Reference: 2'-FLUOROPROPIOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-FLUOROPROPIOPHENONE(21120-36-5)
• EPA Substance Registry System: 2'-FLUOROPROPIOPHENONE(21120-36-5)

Safety Data

• Statements: R36/38:
• Safety Statements: S 22;R36:
• WGK Germany: 3
• Hazardous Substances Data: 21120-36-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 2257, 1980 DOI: 10.1016/0040-4039(80)80018-9

Upstream product

• 349-43-9 ethyl 2-fluoropropionate 
• 6084-17-9 2-chloro-1-phenylpropan-1-one 
• 88208-13-3 2-fluoro-1-phenyl-1-propanol 
• 673-32-5 1-Phenylprop-1-yne 
• 67-56-1 methanol 
• 6202-57-9 2-Chlor-3-methyl-2-phenyloxiran 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 5650-40-8 2-hydroxypropiophenone 
• 39623-95-5 1-phenylprop-1-enyl acetate 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 6202-57-9 chloro-2-phenyl-2-methyl-3-oxiranne (Z) 
• 134414-80-5 N-Fluoro-o-benzenedisulfonimide 
• 93-55-0 1-phenyl-propan-1-one 
• 16205-14-4 2-Methyl-3-phenyl-2H-azirine 

Downstream Products

• 63801-22-9 2-phenylpentan-3-one 
• 63017-06-1 2-bromo-2-fluoropropiophenone 
• 88208-13-3 2-fluoro-1-phenyl-1-propanol 
• 63017-20-9 2-chloro-2-fluoro-1-phenylpropane-1-one 
• 81182-34-5 [2-Fluoro-1-phenyl-prop-(E)-ylidene]-isopropyl-amine 
• 73611-94-6 2-fluoro-1,1-dimethoxy-1-phenylpropane 
• 765271-39-4 methyl 2-fluoro-2-methyl-3-oxo-3-phenylpropionate 
• 121059-34-5 [5-Chloro-2-fluoro-2-methyl-1-phenyl-pent-(E)-ylidene]-isopropyl-amine 
• 1047683-33-9 (Z)-allyl-2-fluoro-1-phenylprop-1-enyl carbonate 
• 1204136-25-3 2-fluoro-1,2-diphenyl-1-propanone 
• 1221794-72-4 n-butyldimethyl[[2-fluoro-(1E)-1-phenyl-1-propenyl]oxy]silane 
• 1221794-73-5 tri-n-propyl[[2-fluoro-(1E)-1-phenyl-1-propenyl]oxy]silane 
• 1221794-74-6 tri-n-butyl[[2-fluoro-(1E)-1-phenyl-1-propenyl]oxy]silane 
• 1221794-76-8 triisobutyl[[2-fluoro-(1E)-1-phenyl-1-propenyl]oxy]silane 

Relevant articles and documents

Rh-Catalyzed arylation of fluorinated ketones with arylboronic acids

The Rh-catalyzed arylation of fluorinated ketones with boronic acids is reported. This efficient process allows access to fluorinated alcohols in high yields under mild conditions. Competition experiments suggest that difluoromethyl ketones are more reactive than trifluoromethyl ketones in this process, despite their decreased electronic activation, an effect we postulate to be steric in origin.

Flow electrochemistry: a safe tool for fluorine chemistry

The heightened activity of compounds containing fluorine, especially in the field of pharmaceuticals, provides major impetus for the development of new fluorination procedures. A scalable, versatile, and safe electrochemical fluorination protocol is conferred. The strategy proceeds through a transient (difluoroiodo)arene, generated by anodic oxidation of an iodoarene mediator. Even the isolation of iodine(iii) difluorides was facile since electrolysis was performed in the absence of other reagents. A broad range of hypervalent iodine mediated reactions were achieved in high yields by coupling the electrolysis step with downstream reactions in flow, surpassing limitations of batch chemistry. (Difluoroiodo)arenes are toxic and suffer from chemical instability, so the uninterrupted generation and immediate use in flow is highly advantageous. High flow rates facilitated productivities of up to 834?mg h?1with vastly reduced reaction times. Integration into a fully automated machine and in-line quenching was key in reducing the hazards surrounding the use of hydrofluoric acid.

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.

Bench-Stable Electrophilic Fluorinating Reagents for Highly Selective Mono- and Difluorination of Silyl Enol Ethers

Efficient methods for the synthesis of fluorinated compounds have been intensively studied, recently. Development of practical fluorinating reagents is indispensable for this purpose. Herein, bench-stable electrophilic fluorinating reagents were synthesized as N-fluorobenzenesulfonimide (NFSI) substitutes. Reagents obtained by replacing one of the NFSI sulfonyl groups with an acyl group led to the highly selective monofluorination of silyl enol ethers with suppression of undesired overreaction, that is, difluorination. On the other hand, reagents bearing electron-withdrawing substituents at NFSI benzenesulfonyl groups efficiently facilitated the difluorination of silyl enol ethers under base-free conditions. Thus, both mono- and difluorinated target materials were prepared from the same substrate.

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.

Formal Fluorinative Ring Opening of 2-Benzoylpyrrolidines Utilizing [1,2]-Phospha-Brook Rearrangement for Synthesis of 2-Aryl-3-fluoropiperidines

A ring expansion of 2-benzoylpyrrolidines, which involves the formal fluorinative ring opening utilizing the [1,2]-phospha-Brook rearrangement under Br?nsted base catalysis and a subsequent intramolecular reductive amination, was developed. The operationally simple three-step protocol provides an efficient access to 2-aryl-3-fluoropiperidines. The methodology was further applied to the syntheses of azepanes and tetrahydroquinolines.

Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy

The discrimination of a fluorine atom from a hydrogen atom has been challenging in asymmetric catalysis. We herein report iridium-catalyzed hydrogenation of α-fluoro ketones using a strategy of dynamic kinetic resolution. Both enantiomeric and diastereomeric selectivities were satisfactory in the preparation of β-fluoro alcohols. The DFT calculation revealed a C-F···Na charge-dipole interaction in the transition state of hydride transfer. This noncovalent interaction would be responsible for the diastereomeric control.

Visible-Light-Assisted Gold-Catalyzed Fluoroarylation of Allenoates

A strategically novel synthetic method for the fluoroarylation of allenic ester was developed that enables the expedient construction of a host of β-fluoroalkyl-containing cinnamate derivatives. The reaction proceeds through visible-light-promoted gold redox catalysis, occurs smoothly under very mild reaction conditions, accommodates a large variety of functional groups, and more importantly allows the incorporation of fluorine and aryl groups with excellent regio- and stereoselectivity. The concomitant activation mode for both the allene motif and the hydrogen fluoride is key for the success of the reaction.

α,α-Alkylation-Halogenation and Dihalogenation of Sulfoxonium Ylides. A Direct Preparation of Geminal Difunctionalized Ketones

A one-pot alkylation–halogenation of ketosulfoxonium ylides in the presence of alkyl halides is described. The method furnishes several gem-difunctionalized haloketones (an alkyl and F, Cl, Br, or I) in good yields. Replacing alkyl halides with a mixture of electrophilic halogen species and various halide anions led to gem-dihalogenated ketones containing a combination of the same or two different halogens. Kinetic isotopic effects as well as reaction kinetic experiments give insight to the mechanism of these reactions.

Decarboxylative fluorination of β-Ketoacids with N-fluorobenzenesulfonimide (NFSI) for the synthesis of α-fluoroketones: Substrate scope and mechanistic investigation

Cesium carbonate (Cs2CO3)-mediated decarboxylative fluorination of β-ketoacids using NFSI in the MeCN/H2O mixed solvent system affords α-fluoroketones with a broad scope. Both electron-rich and electron-deficient α-non-substituted β-ketoacids are amenable to this protocol. The mechanistic study indicates that the reaction proceeds through electrophilic fluorination followed by decarboxylation, which is different from the decarboxylative fluorination of normal carboxylic acids.