655-32-3

Basic information

• Product Name: 2,2,2,4'-TETRAFLUOROACETOPHENONE
• Synonyms: 2,2,2,4'-TETRAFLUOROACETOPHENONE;1-(4-FLUOROPHENYL)-2,2,2-TRIFLUOROETHANONE;ALPHA,ALPHA,ALPHA,4-TETRAFLUOROACETOPHENONE;4-FLUORO-ALPHA,ALPHA,ALPHA-TRIFLUOROACETOPHENONE;4-FLUORO-A,A,A-TRIFLUOROACETOPHENONE;2,2,2-trifluoro-1-(4-fluorophenyl)ethan-1-one;2,2,2-trifluoro-1-(4-fluorophenyl)-ethanon;2,2,2-Trifluoro-1-(4-fluoro-phenyl)-ethanone
• CAS NO: 655-32-3
• Molecular Formula: C₈H₄F₄O
• Molecular Weight: 192.11
• EINECS: 211-509-4
• Product Categories: Fluorine series
• Mol File: 655-32-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 24-27 °C(lit.)
• Boiling Point: 66-67 °C34 mm Hg(lit.)
• Flash Point: 90 °F
• Appearance: /
• Density: 1.37 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.448(lit.)
• Storage Temp.: 0-10°C
• BRN: 1872824
• CAS DataBase Reference: 2,2,2,4'-TETRAFLUOROACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2,4'-TETRAFLUOROACETOPHENONE(655-32-3)
• EPA Substance Registry System: 2,2,2,4'-TETRAFLUOROACETOPHENONE(655-32-3)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 655-32-3(Hazardous Substances Data)

Usage

Description

2,2,2,4'-TETRAFLUOROACETOPHENONE is an organic compound characterized by the presence of four fluorine atoms and an acetophenone group. It is known for its unique chemical properties and reactivity, making it a valuable intermediate in the synthesis of various pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
2,2,2,4'-TETRAFLUOROACETOPHENONE is used as a key intermediate in the stereoselective synthesis of trifluoromethyl-substituted 2H-furan-amines. These compounds are of significant interest due to their potential applications as pharmaceutical agents, particularly in the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
2,2,2,4'-TETRAFLUOROACETOPHENONE is also utilized as a building block in the synthesis of agrochemicals, such as insecticides and herbicides. The introduction of the trifluoromethyl group into these molecules can enhance their biological activity and selectivity, leading to more effective and environmentally friendly products.

Upstream product

• 352-13-6 4-flourophenylmagnesium bromide 
• 76-05-1 trifluoroacetic acid 
• 2923-17-3 lithium trifluoroacetate 
• 407-25-0 trifluoroacetic anhydride 
• 383-63-1 ethyl trifluoroacetate, 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 17556-41-1 2,2,2-trifluoro-1-(4-fluorophenyl)ethanol 
• 459-57-4 4-fluorobenzaldehyde 
• 352-34-1 4-fluoro-1-iodobenzene 
• 201230-82-2 carbon monoxide 
• 354-32-5 trifluoracetyl chloride 
• 462-06-6 fluorobenzene 

Downstream Products

• 1979-54-0 2-p-Fluorphenylpentafluorpropen 
• 65613-24-3 p-Diethylamino-α,α,α-trifluoracetophenon 
• 913832-52-7 4-((4-fluorophenyl)thio)phenyl trifluoromethyl ketone 
• 890085-08-2 (S)-4-fluoro-α,α,α-(trifluoromethyl)-benzenemethanol 
• 848926-12-5 (R)-2,2,2-trifluoro-1-(4'-fluorophenyl)ethanol 
• 849093-96-5 (R)-3-(pyridin-2-yl-methylsulfanyl)-2-[(RS)-2,2,2-trifluoro-1-(4-fluorophenyl)ethylamino]-propionic acid methyl ester 
• 573982-68-0 1-(4-cyclopentylamino-phenyl)-2,2,2-trifluoro-ethanone 
• 123685-50-7 N-[3,4-Dihydro-4-oxo-6-[[2-propynyl[4-(trifluoroacetyl)phenyl]amino]methyl]-2-quinazolinyl]-2,2-dimethylpropanamide 
• 123685-38-1 2-amino-6-[[2-propynyl[4-(trifluoroacetyl)phenyl]amino]methyl]-4(3H)-quinazolinone 
• 141508-99-8 1-(4-(N-methyl-N-(2,2,2-trifluoroethyl)amino)phenyl)-2,2,2-trifluoroethyl 3,5-dinitrobenzoate 
• 141508-98-7 1-(4-(N-methyl-N-(2,2,2-trifluoroethyl)amino)phenyl)-2,2,2-trifluoroethyl pentafluorobenzoate 
• 141508-96-5 1-(4-(N-methyl-N-(2,2,2-trifluoroethyl)amino)phenyl)-2,2,2-trifluoroethanol 
• 141508-97-6 1-(4-(N-(2,2,2-trifluoroethyl)amino)phenyl)-2,2,2-trifluoroethanol 
• 169387-17-1 1,1-Difluor-2-(4-fluorphenyl)-prop-1-en-3,3-bisphosphonsaeuretetraethylester 

Relevant articles and documents

Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction

A novel class of chiral spiro-fused bisoxazoline ligands possessing a deep chiral pocket was prepared. The developed ligands have been employed in the nickel-catalyzed highly enantioselective Michael-type Friedel-Crafts reaction, affording the products bearing a trifluoromethylated all-carbon quaternary stereocenter with moderate to excellent yields (up to 99%) and good to excellent enantioselectivies (up to > 99.9% ee). Moreover, a proposed model of chiral pocket revealed that the attack of indole from the Re-face of β-CF3-β-disubstituted nitroalkene was favorable.

Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

Tertiary alcohols bearing a trifluoromethyl group are of considerable medicinal interest. Using an umpolung strategy, we herein report the first intermolecular reductive cross-coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines with the aid of a Br?nsted acid catalyst upon visible-light irradiation. This metal-free reaction is operationally simple and performed at ambient temperature, allowing access to desired tertiary alcohols with tri-/difluoromethyl groups in moderate to excellent yields. The commercially available and easily handled Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.

Palladium-catalyzed carbonylative coupling of aryl iodides with an organocopper reagent: A straightforward procedure for the synthesis of aryl trifluoromethyl ketones

A palladium-catalyzed carbonylative coupling of aryl iodides with a (trifluoromethyl)copper reagent has been developed. A wide range of substrates have been transformed into their corresponding trifluoromethyl ketones in good to excellent yields under mild conditions with high efficiency and excellent functional-group compatibility. Preliminary mechanistic investigations suggest that the transmetallation of an acylpalladium intermediate with the (trifluoromethyl)copper reagent seems to be involved in the catalytic cycle. Notably, this report represents one of the few studies on carbonylative coupling with organocopper reagents.