703-18-4

Usage

Uses

Used in Pharmaceutical Synthesis:
Phenyl trifluoromethyl sulphoxide is used as a reagent for the synthesis of pharmaceuticals due to its unique reactivity and high selectivity. It aids in the production of various organic compounds that are essential in the development of new drugs and medications.
Used in Organic Chemistry Research:
In the field of organic chemistry, Phenyl trifluoromethyl sulphoxide is utilized as a selective oxidizing agent for conducting various chemical reactions. Its efficiency and selectivity make it a preferred choice for researchers working on complex organic synthesis processes.
Used in Industrial Applications:
Phenyl trifluoromethyl sulphoxide is employed in industrial applications for its stability and relatively low toxicity. Its versatility as an oxidizing agent allows it to be used in the production of a wide range of organic compounds, making it a valuable asset in the chemical industry.

Upstream product

• 456-56-4 phenyl trifluoromethylsulfide 
• 708-67-8 4-aminophenyl trifluoromethylsulfoxide 
• 670-98-4 methyl benzenesulfinate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2926-29-6 Langlois reagent 
• 71-43-2 benzene 
• 394-60-5 1-nitro-4-[(R,S)-(trifluoromethyl)sulfinyl]benzene 
• 1493-13-6 trifluorormethanesulfonic acid 
• 2926-30-9 sodium triflate 
• 403-66-7 p-nitrophenyl trifluoromethyl sulfide 
• 4972-29-6 benzenesulphinyl chloride 

Downstream Products

• 147531-11-1 trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt 
• 95414-68-9 imino(phenyl)(trifluoromethyl)-λ⁶-sulfanone 
• 426-58-4 (trifluoromethylsulfonyl)benzene 
• 456-56-4 phenyl trifluoromethylsulfide 
• 1948-06-7 <3-Nitro-phenyl>-trifluormethyl-sulfoxid 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 120120-26-5 (trifluoromethyl)triethylsilane 
• 536975-47-0 (trifluoromethyl)(t-butyl)dimethylsilane 
• 1178899-29-0 N-butyryl-S-phenyl-S-(trifluoromethyl)sulfilimine 
• 1178899-31-4 N-(methoxyacetyl)-S-phenyl-S-(trifluoromethyl)sulfilimine 
• 1178899-35-8 N-(p-bromobenzoyl)-S-phenyl-S-(trifluoromethyl)sulfilimine 
• 1178899-36-9 N-(o-bromobenzoyl)-S-phenyl-S-(trifluoromethyl)sulfilimine 
• 1178899-32-5 N-(phenylacetyl)-S-phenyl-S-(trifluoromethyl)sulfilimine 
• 1178899-33-6 N-benzoyl-S-phenyl-S-(trifluoromethyl)sulfilimine 

Relevant academic research and scientific papers

Aryl Fluoroalkyl Sulfoxides: Optical Stability and pKa Measurement

The enantiomeric separation of aryl trifluoromethyl and difluoromethyl sulfoxides was realized via chiral chromatography. The configurational stability of each set of enantiomers was then studied by thermal enantiomerization. The ΔG≠ values obt

Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst

We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.

Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents

Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents have become popular reagents for the alkynylation of radicals and nucleophiles, but only offer limited possibilities for further structure and reactivity fine-tuning. Herein, the synthesis o

Optimization and Gram-Scale Preparation of S-Trifluoromethyl Sulfoximines and Sulfilimino Iminiums, Powerful Reagents for the Late Stage Introduction of the CF3 Group

S-Trifluoromethyl sulfoximines and S-trifluoromethyl sulfilimino iminiums are important reagents for the electrophilic or radical late-stage introduction of the CF3 group. We disclose in this article a reappraisal of our previous methodologies

One pot synthesis of trifluoromethyl aryl sulfoxides by trifluoromethylthiolation of arenes and subsequent oxidation with hydrogen peroxide

Hydrogen peroxide was used for oxidation of various aryl trifluoromethyl sulfides. Trifluoroacetic acid was used as an activating solvent that enables non-catalyzed oxidation and increases selectivity for sulfoxide formation. As shown by oxidation of thianthrene TFA enhances electrophilic character of the oxidant and further oxidation of sulfoxide group is blocked. We have joined trifluoromethylthiolation of arenes using a modified Billard reagent (p-ClPhNHSCF3) with oxidation of aryl trifluoromethyl sulfides using 1.2 equiv. of 30% aqueous hydrogen peroxide and this one-pot process has superior yields than would have been obtained in a two step process.

General, practical and selective oxidation protocol for CF3s into CF3S(O) group

A simple and efficient protocol for the oxidation of trifluoromethyl, mono- and difluoromethyl sulfides to the corresponding sulfoxides without over-oxidation to sulfones, using TFPAA prepared in situ from trifluoroacetic acid and 15% H2O2 aqueous solution was developed. The methodology is suitable for a wide range of aromatic and aliphatic substrates in milligram and multigram scales.

Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides

Metal- and additive-free oxidation of a series of sulfides/thioketones has been achieved using cyclic diacyl peroxides as mild oxygen sources. This protocol features simple manipulation, high chemo- and diastereoselectivity, and a broad substrate scope (up to 42 examples), tolerates many common functional groups, and is scalable and applicable to the late-stage sulfoxidation strategy. A preliminary mechanistic study by quantum mechanical calculations suggests that a single two-electron transfer process is energetically more favorable, and indicates the reactivity of cyclic diacyl peroxides distinct from conventional acyclic acyl peroxides.

Palladium-Catalyzed Arylation of Arylboronic Acids with Yagupolskii-Umemoto Reagents

A Pd-catalyzed Suzuki cross-coupling of arylboronic acids with Yagupolskii-Umemoto reagents was explored. In contrary to trifluoromethylations, the Pd-catalyzed reaction of R-B(OH)2 and [Ar2SCF3]+[OTf]- provided the arylation products (R-Ar) in good to high yields. The reaction confirms that the S-Ar bonds of [Ar2SCF3]+[OTf]- can be readily cleaved in the presence of Pd complexes. The relatively electron-poor aryl groups of asymmetric [Ar1Ar2SCF3]+[OTf]- salts are more favorably transferred compared to the electron-rich ones. This reaction represents the first report of utilization of [Ar2SCF3]+[OTf]- as arylation reagents in organic synthesis.

Br?nsted Acid-Mediated Hydrative Arylation of Unactivated Alkynes

The Br?nsted acid-mediated reaction of unactivated alkynes with aryl sulfoxides leads to simultaneous hydration and intermolecular C-C bond formation. This solvent- A nd metal-free transformation directly delivers α-arylated carbonyl compounds as the prod

Photoredox-Catalyzed Stereoselective Conversion of Alkynes into Tetrasubstituted Trifluoromethylated Alkenes

A regio- and stereoselective synthesis of trifluoromethylated alkenes bearing four different substituents has been developed. Stereocontrolled sulfonyloxytrifluoromethylation of unsymmetric internal alkynes with an electrophilic CF3 reagent, namely the triflate salt of the Yagupol'skii-Umemoto reagent, in the presence of an Ir photoredox catalyst under visible-light irradiation afforded trifluoromethylalkenyl triflates with well-predictable stereochemistry resulting from anti addition of the trifluoromethyl and triflate groups. Subsequent palladium-catalyzed cross-couplings led to tetrasubstituted trifluoromethylated alkenes in a highly stereoselective manner. The present method is the first example of a facile one-pot synthesis of tetrasubstituted trifluoromethylated alkenes from simple alkynes.