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

Uses

2,2,2,4''-Tetrafluoroacetophenone is used in the stereoselective synthesis of trifluoromethyl-substituted 2H-furan-amines.

General Description

2,2,2,4′-Tetrafluoroacetophenone (α,α,α,4-Tetrafluoroacetophenone, 2,2,2-trifluoro-1-(4-fluorophenyl)ethanone) is a fluorinated building block. Its enthalpy of vaporization at boiling point has been reported.

Upstream product

• 352-13-6 4-flourophenylmagnesium bromide 
• 76-05-1 trifluoroacetic acid 
• 352-34-1 4-fluoro-1-iodobenzene 
• 122499-13-2 1-iodo-2,5-dioxa-1,3,3,4,6,6,7,7,8,8,8-undecafluoro-1,4-bis(trifluoromethyl)octane 
• 2923-17-3 lithium trifluoroacetate 
• 360-92-9 N,N-diethyl-2,2,2-trifluoroacetamide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 462-06-6 fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 17556-41-1 2,2,2-trifluoro-1-(4-fluorophenyl)ethanol 
• 383-63-1 ethyl trifluoroacetate, 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 711-23-9 (±)-1,1,1-trifluoro-2-(4-fluorophenyl)propan-2-ol 
• 350040-14-1 4-trifluoroacetylphenylhydrazine 
• 1979-54-0 2-p-Fluorphenylpentafluorpropen 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 70783-32-3 2,2,2-trifluoro-1-(4-phenoxyphenyl)-ethanone 
• 916347-78-9 (2S,4R)-4-[(benzylthio)methyl]-2-(4-fluorophenyl)-2-(trifluoromethyl)-1,3-oxazolidine 
• 916347-56-3 (2R,4R)-4-[(benzylthio)methyl]-2-(4-fluorophenyl)-2-(trifluoromethyl)-1,3-oxazolidine 
• 573717-52-9 N-methyl-N-(4-trifluoroacetyl-phenyl)-benzenesulfonamide 
• 655-29-8 1-fluoro-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene 
• 1142905-56-3 2,2,2-trifluoro-1-(4-fluoro-phenyl)-1-[4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-3,5-dimethyl-phenyl]-ethanol 

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.

Asymmetric Construction of Pyrrolidines Bearing a Trifluoromethylated Quaternary Stereogenic Center via CuI-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-CF3-β,β-Disubstituted Nitroalkenes

A direct and convenient method has been developed for the synthesis of optically active pyrrolidines bearing a quaternary stereogenic center containing a CF3 group at the C-3 position of the pyrrolidine ring. The synthesis system, CuI/Si-FOXAP-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides with β-CF3-β,β-disubstituted nitroalkenes, provides pyrrolidines with high diastereoselectivities (up to >98:2 d.r.) and excellent enantioselectivities (up to >99.9 ee) and performs well for a broad scope of substrates under mild conditions.