81577-09-5

Usage

General Description

2-(3-Chlorophenyl)-1,1,1-trifluoroethane, also known as chlorotrifluoroethane, is a halogenated organic compound with the chemical formula C8H5ClF3. It is a colorless, volatile liquid that is used as a refrigerant and as a propellant in aerosol products. It is classified as a hydrochlorofluorocarbon (HCFC) and has been used as a replacement for the ozone-depleting chlorofluorocarbons (CFCs). However, like other HCFCs, chlorotrifluoroethane is considered a greenhouse gas and contributes to global warming. Its use has been regulated and restricted under the Montreal Protocol and other international agreements aimed at protecting the ozone layer and mitigating climate change.

Upstream product

• 81577-14-2 1-Chloro-3-(1-chloro-2,2,2-trifluoro-ethyl)-benzene 
• 84750-91-4 1-chloro-3-(2,2-difluorovinyl)benzene 
• 873-63-2 m-chlorobenzyl alcohol 
• 129946-88-9 Umemoto's reagent 

Downstream Products

• 309-12-6 1-chloro-3-(1,1-dichloro-2,2,2-trifluoro-ethyl)-benzene 
• 81577-14-2 1-Chloro-3-(1-chloro-2,2,2-trifluoro-ethyl)-benzene 

Relevant academic research and scientific papers

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

Study on the addition of hydrogen fluoride to 2',2'-difluorostyrenes

2,2,2-Trifluoroethylarenes were obtained in good yield from the addition of KF to 2',2'-difluorostyrenes in the presence of crown ether. A linear regression line obtained from correlation between log(reaction rate) and Hammett constants with slope of +4.28 suggested that this addition process is very sensitive to the substituents on the phenyl ring.

Novel Synthesis of 2,2,2-Trifluoroethyl Compounds from Homoallylic Alcohols: A Copper(I) Iodide-initiated Trifluoromethyl-Dehydroxylation Process

Benzyl, prop-2-enyl and allyl chlorodifluoroacetates 3a, bromodifluoroacetates 3b or fluorosulfonyldifluoroacetates 3c, when decomposed in the presence of 1 equivalent of copper(I) iodide at an appropriate temperature in dimethylformamide, gave the corresponding trifluoromethyl derivatives in good to excellent yields.The products can also be obtained directly by ester exchange of XCF2CO2Et (X = FSO2, Cl, Br) 6 and the corresponding alcohols in the presence of KF and CuI.A trifluoromethylation-dehydroxylation mechanism, initiated by CuI, is proposed.

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.