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147531-11-1

147531-11-1

Identification

  • Product Name:Diphenyl(trifluoromethyl)sulfonium trifluoromethanesulfonate

  • CAS Number: 147531-11-1

  • EINECS:

  • Molecular Weight:404.354

  • Molecular Formula: CF3O3S*C13H10F3S

  • HS Code:29339900

  • Mol File:147531-11-1.mol

Synonyms:diphenyl-(trifluoromethyl)-sulfonium trifluoromethanesulfonate;

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Diphenyl(trifluoromethyl)sulfoniumtrifluoromethanesulfonate
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Relevant articles and documentsAll total 12 Articles be found

New Electrophilic Trifluoromethylating Agents

Yang, Jing-Jing,Kirchmeier, Robert L.,Shreeve, Jean'ne M.

, p. 2656 - 2660 (1998)

Synthetic routes to S-(trifluoromethyl)phenyl-4-fluorophenylsulfonium triflate (8), S-(trifluoromethyl)phenyl-2,4-difluorophenylsulfonium triflate (9), S-(trifluoromethyl)phenyl-3-nitrophenylsulfonium triflate (10), and S-(trifluoromethyl)-4-fluorophenyl-3-nitrophenylsulfonium triflate (11) are described. They are stable molecules and conveniently prepared by treating phenyl trifluoromethyl sulfoxide with benzene and its derivatives. These novel electrophilic trifluoromethylating agents react under mild conditions with a variety of aromatic rings (p-hydroquinone, pyrrole, and aniline) to give trifluoromethylated compounds (2-trifluoromethyl-p-hydroquinone, 2-trifluoromethylpyrrole, 2-trifluoromethylaniline, and 4-trifluoromethylaniline) in moderate to high yields. The electrophilic trifluoromethylating potential can be altered by placing electron-withdrawing substituents on the benzene rings.

Straightforward one-pot synthesis of trifluoromethyl sulfonium salts

Magnier, Emmanuel,Blazejewski, Jean-Claude,Tordeux, Marc,Wakselman, Claude

, p. 1279 - 1282 (2006)

(Chemical Equation Presented) Mix and wait: Trifluoromethyl sulfonium salts that are able to react as reagents in the trifluoromethylation of various nucleophiles are formed in a multicomponent reaction. The desired electrophilic reagents are prepared fro

Visible-Light Photocatalytic Tri- A nd Difluoroalkylation Cyclizations: Access to a Series of Indole[2,1- A[isoquinoline Derivatives in Continuous Flow

Yuan, Xin,Duan, Xiu,Cui, Yu-Sheng,Sun, Qi,Qin, Long-Zhou,Zhang, Xin-Peng,Liu, Jie,Wu, Meng-Yu,Qiu, Jiang-Kai,Guo, Kai

supporting information, p. 1950 - 1954 (2021/04/05)

A process for achieving photocatalyzed tri- A nd difluoromethylation/cyclizations for constructing a series of tri-or difluoromethylated indole[2,1-a]isoquinoline derivatives is described. This protocol utilized an inexpensive organic photoredox catalyst and provided good yields. Moreover, the combination of continuous flow and photochemistry, designed to provide researchers with a unique green process, was also shown to be key to allowing the reaction to proceed (product yield of 83% in flow vs 0% in batch).

Cu-Mediated Trifluoromethylation of Aromatic α-Diazo Esters with the Yagupolskii–Umemoto Reagent

Hu, Xiao-Qian,Han, Jia-Bin,Zhang, Cheng-Pan

supporting information, p. 324 - 331 (2017/01/24)

Reductive trifluoromethylation of aromatic α-diazo esters at room temperature with the Yagupolskii–Umemoto reagent {[Ph2SCF3][OTf]; (2a)} in DMF in the presence of excess CuCl gave a variety of α-trifluoromethyl arylacetates in up to

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

Wang, Shi-Meng,Wang, Xiao-Yan,Qin, Hua-Li,Zhang, Cheng-Pan

supporting information, p. 6542 - 6546 (2016/05/02)

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.

Photoredox-Catalyzed Stereoselective Conversion of Alkynes into Tetrasubstituted Trifluoromethylated Alkenes

Tomita, Ren,Koike, Takashi,Akita, Munetaka

, p. 12923 - 12927 (2015/11/02)

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.

PENTAFLUOROSULFANYL PHTHALOCYANINE DERIVATIVES AND INTERMEDIATES THEREOF

-

Paragraph 0102-0104, (2015/12/07)

Provided is a phthalocyanine derivative of the following general formula (1) which has superior solubility in organic solvents: General formula (1): (wherein M is a hydrogen atom, a metal element, a metalloid element, a metal oxide, a metalloid oxide, a m

Process route upstream and downstream products

Process route

phenyl trifluoromethyl sulfoxide
703-18-4

phenyl trifluoromethyl sulfoxide

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt
147531-11-1

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt

Conditions
Conditions Yield
With trifluoromethylsulfonic anhydride; In benzene;
40%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

potassium triflinate
41804-89-1

potassium triflinate

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt
147531-11-1

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt

Conditions
Conditions Yield
77%
In dichloromethane; at 20 ℃; for 16h;
60%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

phenyl trifluoromethyl sulfoxide
703-18-4

phenyl trifluoromethyl sulfoxide

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt
147531-11-1

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt

Conditions
Conditions Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane; benzene; for 96h; Ambient temperature;
59%
In benzene; at 0 - 20 ℃; for 24h; Inert atmosphere;
50%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Langlois reagent
2926-29-6

Langlois reagent

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt
147531-11-1

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt

Conditions
Conditions Yield
In dichloromethane; at 0 - 20 ℃; for 34h; Inert atmosphere;
38%
In dichloromethane; at 0 - 20 ℃; for 35.5h; Inert atmosphere;
38%
In dichloromethane; at 0 - 20 ℃; Inert atmosphere; Cooling with ice;
25%
In dichloromethane; at 0 - 20 ℃; for 35.5h; Inert atmosphere;
25%
In dichloromethane; at 0 - 20 ℃; for 35.5h; Inert atmosphere;
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

phenyl trifluoromethyl sulfoxide
703-18-4

phenyl trifluoromethyl sulfoxide

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt
147531-11-1

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt

Conditions
Conditions Yield
at 0 - 20 ℃; Mechanism; other benzene derivatives: fluorobenzene, 1,3-difluorobenzene;
85%
1.) 0 deg C, 1 h, 2.) room temperature, 24 h;
85%
at 0 ℃; for 1h; Inert atmosphere;
54%
phenyl trifluoromethylsulfide
456-56-4

phenyl trifluoromethylsulfide

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt
147531-11-1

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 10 h / 0 °C / Inert atmosphere
2: benzene / 24 h / 0 - 20 °C / Inert atmosphere
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; benzene;
9-phenanthrenylboronic acid
68572-87-2

9-phenanthrenylboronic acid

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt
147531-11-1

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt

2,2‐difluoro‐2‐(triphenylphosphonio)acetate

2,2‐difluoro‐2‐(triphenylphosphonio)acetate

9-(difluoro(phenyl)methyl)phenanthrene

9-(difluoro(phenyl)methyl)phenanthrene

Conditions
Conditions Yield
With tetrakis(triphenylphosphine) palladium(0); Bathocuproine; caesium carbonate; In para-xylene; at 65 ℃; for 6h; Inert atmosphere;
41%
trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt
147531-11-1

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt

4-ethoxyphenylacetylene
79887-14-2

4-ethoxyphenylacetylene

1-ethoxy-4-(3,3,3-trifluoroprop-1-yn-1-yl)benzene
1464776-39-3

1-ethoxy-4-(3,3,3-trifluoroprop-1-yn-1-yl)benzene

Conditions
Conditions Yield
With [2,2]bipyridinyl; copper(l) iodide; potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 6h;
83%
1-phenylbut-2-en-1-one
495-41-0

1-phenylbut-2-en-1-one

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt
147531-11-1

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt

4,4,4-trifluoro-3-methyl-1-phenylbutan-1-one
106352-39-0

4,4,4-trifluoro-3-methyl-1-phenylbutan-1-one

Conditions
Conditions Yield
With copper; In water; dimethyl sulfoxide; at 60 ℃; for 12h; regioselective reaction; Inert atmosphere;
36%
benzalacetophenone
94-41-7

benzalacetophenone

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt
147531-11-1

trifluoromethanesulfonic acid diphenyl(trifluoromethyl)sulfonium salt

(3R)-4,4,4-trifluoro-1,3-diphenylbutan-1-one

(3R)-4,4,4-trifluoro-1,3-diphenylbutan-1-one

Conditions
Conditions Yield
With copper; In water; dimethyl sulfoxide; at 60 ℃; for 12h; Reagent/catalyst; Solvent; regioselective reaction; Inert atmosphere;
37%

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