2836-82-0

Basic information

• Product Name: 2-Fluorophenylacetone
• Synonyms: 2-FLUOROPHENYLACETONE;2-FLUOROPHENYLACETONE 99% (GC);2-Fluorophenylacetone 99%;2-Fluorophenylacetone99%;o-Fluorophenylacetone;1-(2-Fluorophenyl)acetone;1-(2-Fluorophenyl)-2-propanone;1-(2-Oxopropyl)-2-fluorobenzene
• CAS NO: 2836-82-0
• Molecular Formula: C₉H₉FO
• Molecular Weight: 152.17
• EINECS: 220-627-5
• Product Categories: Aromatic Ketones (substituted);C9;Carbonyl Compounds;Ketones
• Mol File: 2836-82-0.mol

Chemical Properties

• Boiling Point: 47 °C0.05 mm Hg(lit.)
• Flash Point: 185 °F
• Appearance: Pale yellow/Liquid
• Density: 1.077 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00877mmHg at 25°C
• Refractive Index: n20/D 1.4989(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-Fluorophenylacetone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluorophenylacetone(2836-82-0)
• EPA Substance Registry System: 2-Fluorophenylacetone(2836-82-0)

Safety Data

• Hazard Codes: F
• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 2836-82-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluorophenylacetone is used as a key intermediate in the synthesis of antimalarial drugs, contributing to the development of medications that combat malaria, a prevalent and life-threatening disease worldwide.
Used in Chemical Synthesis:
2-Fluorophenylacetone is used as a synthetic building block for the production of 6-methyluracils, which are important compounds in the field of organic chemistry and have potential applications in various chemical processes.
Used in Organic Chemistry:
Upon reaction with chlorosulfonyl isocyanate, 2-Fluorophenylacetone yields 5-(2-fluorophenyl)-6-methyl-1,3-oxazine-2,4-(3H)-dione, a compound with potential applications in the development of new pharmaceuticals and other chemical products.

InChI:InChI=1/C9H9FO/c1-7(11)6-8-4-2-3-5-9(8)10/h2-5H,6H2,1H3

Upstream product

• 103-79-7 1-phenyl-acetone 
• 79-24-3 Nitroethane 
• 446-52-6 2-Fluorobenzaldehyde 
• 108-22-5 Isopropenyl acetate 
• 446-46-8 2-fluorobenzenediazonium tetrafluoroborate 
• 348-52-7 1-Fluoro-2-iodobenzene 
• 123-54-6 acetylacetone 
• 348-54-9 2-Fluoroaniline 
• 56314-65-9 1-allyl-2-fluorobenzene 
• 1072-85-1 o-fluorobromobenzene 
• 67-64-1 acetone 
• 348-51-6 1-chloro-2-fluorobenzene 
• 917-54-4 methyllithium 
• 451-82-1 (2-fluorophenyl)acetic acid 

Downstream Products

• 21906-05-8 3-(2'-fluorophenyl)butan-2-one 
• 1215737-81-7 6-[2-(2-fluorobenzyl)-2-hydroxypropyl]-2,4-dimethoxy-5-phenylpyrimidine 
• 1188495-92-2 (R)-1-(2-fluorophenyl)propan-2-ol 
• 549529-09-1 1-(2-fluorophenyl)propan-2-ol 
• 256526-08-6 (S)-1-(2-fluorophenyl)propan-2-ol 
• 957798-38-8 5,5-Diethoxy-3-(2-fluorophenyl)pentan-2-one 
• 1450816-94-0 1-fluoro-2-(2-methoxypropyl)benzene 
• 1450816-80-4 (E)-ethyl 3-(3-fluoro-2-(2-methoxypropyl)phenyl)acrylate 
• 1456718-32-3 3-(2-fluorophenyl)-2-methyl-1H-indole 

Relevant articles and documents

Gold-Catalyzed [3+2]-Annulations of α-Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity

This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.

Markovnikov Wacker-Tsuji Oxidation of Allyl(hetero)arenes and Application in a One-Pot Photo-Metal-Biocatalytic Approach to Enantioenriched Amines and Alcohols

The Wacker-Tsuji aerobic oxidation of various allyl(hetero)arenes under photocatalytic conditions to form the corresponding methyl ketones is presented. By using a palladium complex [PdCl2(MeCN)2] and the photosensitizer [Acr-Mes]ClO4 in aqueous medium and at room temperature, and by simple irradiation with blue led light, the desired carbonyl compounds were synthesized with high conversions (>80%) and excellent selectivities (>90%). The key process was the transient formation of Pd nanoparticles that can activate oxygen, thus recycling the Pd(II) species necessary in the Wacker oxidative reaction. While light irradiation was strictly mandatory, the addition of the photocatalyst improved the reaction selectivity, due to the formation of the starting allyl(hetero)arene from some of the obtained by-products, thus entering back in the Wacker-Tsuji catalytic cycle. Once optimized, the oxidation reaction was combined in a one-pot two-step sequential protocol with an enzymatic transformation. Depending on the biocatalyst employed, i. e. an amine transaminase or an alcohol dehydrogenase, the corresponding (R)- and (S)-1-arylpropan-2-amines or 1-arylpropan-2-ols, respectively, could be synthesized in most cases with high yields (>70%) and in enantiopure form. Finally, an application of this photo-metal-biocatalytic strategy has been demonstrated in order to get access in a straightforward manner to selegiline, an anti-Parkinson drug. (Figure presented.).

An Efficient Palladium-Catalyzed α-Arylation of Acetone below its Boiling Point

The monoarylation of acetone is a powerful transformation, but is typically performed at temperatures significantly in excess of its boiling point. Conditions described for performing the reaction at ambient temperatures led to significant dehalogenation when applied to a complex aryl halide. We describe our attempts to overcome both issues in the context of our drug-discovery program.

Porphyrins as Photoredox Catalysts in Csp2-H Arylations: Batch and Continuous Flow Approaches

We have investigated both batch and continuous flow photoarylations of enol-acetates to yield different α-arylated aldehyde and ketone building blocks by using diazonium salts as the aryl-radical source. Different porphyrins were used as SET photocatalysts, and photophysical as well as electrochemical studies were performed to rationalize the photoredox properties and suggest mechanistic insights. Notably, the most electron-deficient porphyrin (meso-tetra(pentafluorophenyl)porphyrin) shows the best photoactivity as an electron donor in the triplet excited state, which was rationalized by the redox potentials of excited states and the turnover of the porphyrins in the photocatalytic cycle. A two-step continuous protocol and multigram-scale reactions are also presented revealing a robust, cost-competitive, and easy methodology, highlighting the significant potential of porphyrins as SET photocatalysts.

PROCESS FOR THE PREPARATION OF LACTAMS FROM GLYOXYLIC ACID

A process for the synthesis of lactams suitable for use in antimicrobial, anti-biofilm bacteriostatic compositions.

Carbazolyl phosphorus ligand as well as preparation method and application thereof

The invention is suitable for the technical fields of organic compounds and synthesis, and provides a carbazolyl phosphorus ligand as well as a preparation method and application thereof. The carbazolyl phosphorus ligand is one of a compound 1, a compound 2 and a compound 3 with structures shown by a formula 1, a formula 2 and a formula 3 (shown in the description) respectively, wherein R1 is phenyl or alkyl, R2, R3, R4, R5, R6, R7, R8 and R9 independently are one of hydrogen, C5-C10 alkyl, methoxyl, oxymethyl, ethyoxyl, phenyl, fluorine group, and pyridyl; and R2, R3, R4, and R5 cannot be hydrogen at the same time.

Preparation of a highly congested carbazoyl-derived p,n-type phosphine ligand for acetone monoarylations

We report a newly developed carbazoyl-derived P,N-type phosphine ligand (L1) for the monoarylation of acetone with aryl chlorides. The proposed Pd(dba)2/L1 catalyst exhibited remarkable catalytic reactivity toward highly electron rich and sterically congested aryl chlorides, with catalyst loading as low as 0.1 mol % of Pd along with excellent chemoselectivity. A reaction rate study of the system using electronically diverse aryl chlorides determined the mechanisms regarding the rate-limiting steps in this reaction. The oxidative addition adduct of Pd-PhenCar-Phos with p-chlorotoluene showed the participation of N-Pd coordination in the metal complex. The isolated palladium complex C1 could be utilized as a precatalyst in the transformation and achieved performance comparable to that of the in situ generated palladium species.

Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides

The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts previous findings regarding the α-arylation of acetone with aryl halides.

ELECTRFLUORATION EN POSITION BENZYLIQUE DANS LE SULFOLANE

The use of sulfolane as a solvent instead of acetonitrile in the electrofluorination of benzylic derivatives 1, (R=H, Cl) gives greater yields of benzylic fluorides 2, since the formation of acetamide byproducts 4 is prevented.However, the parallel fluorination of the aromatic nucleus is not avoided under these conditions.