50561-99-4

Basic information

• Product Name: 1-FLUORO-4-(2,2,2-TRIFLUOROETHYL)BENZENE
• Synonyms: 1-FLUORO-4-(2,2,2-TRIFLUOROETHYL)BENZENE
• CAS NO: 50561-99-4
• Molecular Formula: C₈H₆F₄
• Molecular Weight: 178.1268528
• Mol File: 50561-99-4.mol

Chemical Properties

• Boiling Point: 129.4°C at 760 mmHg
• Flash Point: 18°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 12.5mmHg at 25°C
• Refractive Index: 1.421
• CAS DataBase Reference: 1-FLUORO-4-(2,2,2-TRIFLUOROETHYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-FLUORO-4-(2,2,2-TRIFLUOROETHYL)BENZENE(50561-99-4)
• EPA Substance Registry System: 1-FLUORO-4-(2,2,2-TRIFLUOROETHYL)BENZENE(50561-99-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 50561-99-4(Hazardous Substances Data)

Usage

General Description

1-fluoro-4-(2,2,2-trifluoroethyl)benzene, also known as 1-fluoro-4-(2,2,2-trifluoroethyl)benzene, is a chemical compound with the molecular formula C8H6F4. It is a colorless liquid with a strong, sweet odor. This chemical is primarily used in the production of various industrial and pharmaceutical compounds, including agrochemicals, pesticides, and pharmaceuticals. It is also used as a solvent in organic synthesis and as a reagent in chemical reactions. Additionally, 1-fluoro-4-(2,2,2-trifluoroethyl)benzene is also used in research and development as a versatile building block for the synthesis of a wide range of organic compounds. However, it is important to handle this chemical with caution, as it is considered to be harmful if swallowed, and can cause severe skin and eye irritation.

InChI:InChI=1/C8H6F4/c9-7-3-1-6(2-4-7)5-8(10,11)12/h1-4H,5H2

Upstream product

• 50562-20-4 Toluene-4-sulfonic acid 2,2,2-trifluoro-1-(4-fluoro-phenyl)-ethyl ester 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 352-13-6 4-flourophenylmagnesium bromide 
• 75-88-7 1,1,1-trifluoro-2-chloroethane 
• 459-46-1 4-Fluorobenzyl bromide 
• 223761-28-2 (4-fluorobenzyl)zinc(II) bromide 
• 1895006-01-5 dimesityl(trifluoromethyl)sulfonium trifluoromethanesulfonate 
• 352-32-9 p-fluorotoluene 
• 1680206-12-5 Grushin’s reagent 
• 887144-97-0 Togni's reagent 
• 405-50-5 p-Fluorophenylacetic acid 
• 459-56-3 4-fluorobenzylic alcohol 
• 129946-88-9 Umemoto's reagent 
• 81290-20-2 (trifluoromethyl)trimethylsilane 

Downstream Products

• 81577-13-1 1-(1-Chloro-2,2,2-trifluoro-ethyl)-4-fluoro-benzene 
• 81577-15-3 1-(1-Bromo-2,2,2-trifluoroethyl)-4-fluorobenzene 
• 1743-00-6 4-fluoro-β,β-difluorostyrene 

Relevant articles and documents

Csp3-Csp3 Bond-Forming Reductive Elimination from Well-Defined Copper(III) Complexes

Carbon-carbon bond-forming reductive elimination from elusive organocopper(III) complexes has been considered the key step in many copper-catalyzed and organocuprate reactions. However, organocopper(III) complexes with well-defined structures that can undergo reductive elimination are extremely rare, especially for the formation of Csp3-Csp3 bonds. We report herein a general method for the synthesis of a series of [alkyl-CuIII-(CF3)3]- complexes, the structures of which have been unequivocally characterized by NMR spectroscopy, mass spectrometry, and X-ray crystal diffraction. At elevated temperature, these complexes undergo reductive elimination following first-order kinetics, forming alkyl-CF3 products with good yields (up to 91%). Both kinetic studies and DFT calculations indicate that the reductive elimination to form Csp3-CF3 bonds proceeds through a concerted transition state, with a ΔH? = 20 kcal/mol barrier.

Copper-Catalyzed Trifluoromethylation of Alkyl Bromides

Copper oxidative addition into organohalides is a challenging two-electron process. In contrast, formal oxidative addition of copper to C sp2 carbon-bromine bonds can be accomplished by employing latent silyl radicals under photoredox conditions. This novel paradigm for copper oxidative addition has now been applied to a Cu-catalyzed cross-coupling of C sp3-bromides. Specifically, a copper/photoredox dual catalytic system for the coupling of alkyl bromides with trifluoromethyl groups is presented. This operationally simple and robust protocol successfully converts a variety of alkyl, allyl, benzyl, and heterobenzyl bromides into the corresponding alkyl trifluoromethanes.

Copper-Mediated Trifluoromethylation of Benzylic Csp3?H Bonds

Trifluoromethyl-containing compounds play a significant role in medicinal chemistry, materials and fine chemistry. Although direct C?H trifluoromethylation has been achieved on Csp2?H bonds, direct conversion of Csp3?H bonds to Csp3?CF3 remains challenging. We report herein an efficient protocol for the selective trifluoromethylation of benzylic C?H bonds. This process is mediated by a combination CuIII?CF3 species and persulfate salts. A wide range of methylarenes can be selectively trifluoromethylated at the benzylic positions. A combination of experimental and theoretical mechanistic studies suggests that the reaction involves a radical intermediate and a CuIII?CF3 species as the CF3 transfer reagent.

Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, al

METHOD FOR PRODUCING (FLUOROALKYL) ARENE

PROBLEM TO BE SOLVED: To provide a method for efficiently producing fluoroalkyl arene, which is important as synthetic raw materials for medicines and functional materials. SOLUTION: A fluoroalkyl arene is produced by the reaction between an aryl metal species represented by formula (2) and a fluoroalkyl halide represented by formula (3) in the presence of a cobalt compound and an ethylenediamine derivative. In the formula (2) shown in the following figure, R11-R15 independently represent H, a C1-C4 alkyl group or the like. In the formula (3): Y-Rf, Y is Cl or the like; Rf is a C2-C3 fluoroalkyl group. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Cobalt/diamine-catalyzed 1,1-difluoroethylation and 2,2,2-trifluoroethylation of aryl Grignard reagents with corresponding fluoroalkyl halides

Cobalt/diamine-catalyzed 1,1-difluoroethylation and 2,2,2-trifluoroethylation of aryl Grignard reagents with 1,1-difluoroethyl and 2,2,2-trifluoroethyl halides were investigated. With regard to the 1,1-difluoroethylation, 1,2-bis(dimethylamino)-2-methylpropane, which has been rarely used in the cross-coupling reactions, gave the highest yield among the diamine ligands tested. In the 2,2,2-trifluoroethylation, trans-1,2-bis(dimethylamino)cyclohexane provided the desired products in satisfactory yields with not only 2,2,2-trifluoroethyl iodide but also chloride. This Co/diamine catalyst was also effective for the coupling with other partially fluorinated alkyl halides in the presence of appropriate diamine ligands.

Copper-mediated deoxygenative trifluoromethylation of benzylic xanthates: Generation of a C-CF3 bond from an O-based electrophile

The conversion of an alcohol-based functional group, into a trifluoromethyl analogue is a desirable transformation. However, few methods are capable of converting O-based electrophiles into trifluoromethanes. The copper-mediated trifluoromethylation of benzylic xanthates using Umemoto's reagent as the source of CF3 to form C-CF3 bonds is described. The method is compatible with an array of benzylic xanthates bearing useful functional groups. A preliminary mechanistic investigation suggests that the C-CF3 bond forms by reaction of the substrate with in situ generated CuCF3 and CuOTf. Further evidence suggests that the reaction could proceed via a radical cation intermediate. Highly compatible and useful: The copper-mediated trifluoromethylation of benzylic xanthates using Umemoto's reagent as the source of CF3 to form C-CF3 bonds is described (see scheme). The method is compatible with an array of benzylic xanthates bearing useful functional groups. A preliminary mechanistic investigation suggests that the C-CF3 bond forms by reaction of the substrate with in situ generated CuCF3 and CuOTf. Copyright

A simple, rapid procedure for nucleophilic radiosynthesis of aliphatic [18F]trifluoromethyl groups

A procedure for the radiosynthesis of aliphatic [18F] trifluoromethyl groups by reacting 1,1-difluorovinyl precursors with [ 18F]fluoride ions, resulting in the equivalent of direct nucleophilic addition of H[18F]F, has been developed. A variety of 18F-labelled model compounds were then obtained and two potential [18F]radiotracers were synthesised by a two step process starting from 1,1-difluorovin-2-yl 4-toluenesulfonate. The method is widely applicable for the synthesis of novel radiotracers in high radiochemical yields and good specific activity.

MECHANISMS OF FREE-RADICAL REACTIONS. XIII. MECHANISM AND SELECTIVITY OF THE FREE-RADICAL HALOGENATION OF ALKYL AROMATIC HYDROCARBONS WITH FLUOROALKYL SUBSTITUENTS

The free-radical chlorination and bromination of 1-fluoro-2-arylethanes and 1,1,1-trifluoro-2-arylethanes was studied by the method of competing reactions.In all cases a good correalation between log krel and the Brown ?+ constants was observed.The variation of the selectivity in the transition from one reaction series to the other indicates that two independent factors which determine the reactivity (the change in the dissociation energy of the C-H bond and the polar effect of the substituents) have a simultaneous effect.