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

• 2923-17-3 lithium trifluoroacetate 
• 352-13-6 4-flourophenylmagnesium bromide 
• 360-92-9 N,N-diethyl-2,2,2-trifluoroacetamide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 383-63-1 ethyl trifluoroacetate, 
• 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 
• 340-07-8 N-(trifluoroacetyl)piperidine 

Downstream Products

• 1079392-77-0 (R)-1,1,1-trifluoro-2-(4-fluorophenyl)-3-nitropropan-2-ol 
• 1096375-83-5 (R)-2,2,2-trifluoro-1-(4-fluorophenyl)-1-(1H-pyrrol-2-yl)ethanol 
• 1254939-31-5 1,1,1-trifluoro-2-(4-fluorophenyl)pent-4-en-2-ol 
• 1248342-81-5 C₂₀H₁₄F₄ 
• 1255766-46-1 N,N'-{[2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene]di-4,1-phenylene}bis[2-(1-pyrrolidinyl)acetamide] 
• 1255768-08-1 N,N'-{[2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene]di-4,1-phenylene}bis(2-bromoacetamide) 
• 1255768-05-8 4,4'-[2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene]dianiline 
• 1558010-32-4 (S)-2,2,2-trifluoro-1-(4-fluorophenyl)-1-(m-tolyl)ethan-1-ol 
• 916347-78-9 (2S,4R)-4-[(benzylthio)methyl]-2-(4-fluorophenyl)-2-(trifluoromethyl)-1,3-oxazolidine 

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.

Copper-Mediated Trifluoroacetylation of Arenediazonium Salts with Ethyl Trifluoropyruvate

A copper-mediated trifluoroacetylation of various arenediazonium salts with ethyl trifluoropyruvate is reported. The reaction proceeded smoothly under mild conditions at room temperature giving trifluoromethyl aryl ketones in moderate to good yields. A variety of functional groups, including methoxy, hydroxy, ester, ketone, trifluoromethyl, and halide groups, were well tolerated. A possible reaction mechanism involving an aryl radical intermediate was proposed and supported by experimental evidence. This reaction provides a new route to trifluoromethyl aryl ketones, notable synthetic targets, from the corresponding anilines.