456-56-4

Basic information

• Product Name: Trifluoromethylthiobenzene
• Synonyms: [(Trifluoromethyl)sulfanyl]benzene;Benzene, [(trifluoromethyl)thio]-;ALPHA,ALPHA,ALPHA-TRIFLUOROTHIOANISOLE;PHENYL TRIFLUOROMETHYL SULFIDE;PHENYL TRIFLUOROMETHYL SULPHIDE;(TRIFLUOROMETHYLTHIO)BENZENE;TRIFLUOROMETHYL PHENYL SULFIDE;Trifluoromethyl phenyl sulphide~(Trifluoromethylthio)benzene~alpha,alpha,alpha-Trifluorothioanisole
• CAS NO: 456-56-4
• Molecular Formula: C7H5F3S
• Molecular Weight: 178.17
• EINECS: 207-270-0
• Product Categories: Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 456-56-4.mol
• Article Data: 75

Chemical Properties

• Boiling Point: 142 °C(lit.)
• Flash Point: 100 °F
• Appearance: /
• Density: 1.249 g/mL at 25 °C(lit.)
• Vapor Pressure: 33.3mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Sensitive: Stench
• BRN: 2043134
• CAS DataBase Reference: Trifluoromethylthiobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: Trifluoromethylthiobenzene(456-56-4)
• EPA Substance Registry System: Trifluoromethylthiobenzene(456-56-4)

Safety Data

• Hazard Codes: T
• Statements: 10-36/37/38
• Safety Statements: 16-36-36/37/39-23
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 456-56-4(Hazardous Substances Data)

Usage

Uses

Phenyl trifluoromethyl sulfide may be used in the preparation of: sulfoxides, dithiane dioxide, and dithiolane dioxide via iron-catalyzed oxidation of sulfides, dithiane, or dithiolane with hydrogen peroxidebenzophenone hydrazone derivativestrifluoro- and difluoromethylsilanes by reductive coupling of fluoromethyl sulfones, sulfoxides and sulfides with chlorosilanes

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 4047, 1985 DOI: 10.1021/jo00221a017Synthesis, p. 721, 1975 DOI: 10.1055/s-1975-23905

General Description

Phenyl trifluoromethyl sulfide (PTFMS) is an aryl trifluoromethyl sulfide. PTFMS with (triethylgermyl)sodium forms a reagent system that has been employed for the trifluoromethylation of certain imines. The reaction between OH radical and PTFMS has been analyzed using pulse radiolysis technique and quantum chemical calculations.

InChI:InChI=1/C7H5F3S/c8-7(9,10)11-6-4-2-1-3-5-6/h1-5H

Upstream product

• 2923-16-2 potassium trifluoroacetate 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 108-86-1 bromobenzene 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 591-50-4 iodobenzene 
• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 75-63-8 Bromotrifluoromethane 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 5285-87-0 phenyl thiocyanate 
• 7433-56-9 (E)-5-decene 
• 60933-15-5 phenyl trifluoromethanethiosulfonate 
• 821-95-4 1-undecene 

Downstream Products

• 426-58-4 (trifluoromethylsulfonyl)benzene 
• 366-96-1 4-trifluoromethylsulfanyl-m-phenylenediamine 
• 144434-16-2 Phenyl-(2,2,2-trifluoro-1-furan-2-yl-ethyl)-amine 
• 26902-72-7 1,1,1-Trifluorododecan-2-one 
• 141023-04-3 1,1,1-trifluoro-11-dodecen-2-one 
• 703-18-4 phenyl trifluoromethyl sulfoxide 
• 89076-25-5 (4-chloro-phenyl)-(4-trifluoromethylsulfanyl-phenyl)-methanone 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2314-97-8 iodotrifluoromethane 
• 333353-03-0 1,2-bis(trifluoromethylthio)benzene 
• 407-16-9 4-chlorophenyl trifluoromethyl sulfide 

Relevant articles and documents

New stable reagents for the nucleophilic trifluoromethylation. Part 4: Trifluoromethylation of disulfides and diselenides with hemiaminals of trifluoroacetaldehyde

Hemiaminals of fluoral and derivatives have been previously described as efficient new reagents for the nucleophilic trifluoromethylation of carbonyl compounds. Their use has been extended to the synthesis of trifluoromethyl sulfides and selenides from di

Reactions of bromotrifluoromethane and related halides: Synthesis of trifluoromethyl sulphides from disulphides

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Gold (I/III)-Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides

The first C?SCF3/SeCF3 cross-coupling reactions using gold redox catalysis [(MeDalphos)AuCl], AgSCF3 or Me4NSeCF3, and organohalides as substrates are reported. The new methodology enables a one-stop shop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio- and selenoethers with a broad substrate scope (>60 examples with up to 97 % isolated yield). The method is scalable, and its robustness is evidenced by the late-stage functionalization of various bioactive molecules, which makes this reaction an attractive alternative in the synthesis of trifluoromethylthio- and selenoethers for pharmaceutical and agrochemical research and development.

Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF3+, CF3?, and CF3-Reactivity

Here we report the synthesis and application of trifluoromethyl thianthrenium triflate (TT-CF3+OTf-) as a novel trifluoromethylating reagent, which is conveniently accessible in a single step from thianthrene and triflic anhydride. We demonstrate the use of TT-CF3+OTf- in electrophilic, radical, and nucleophilic trifluoromethylation reactions.

Copper(I)-promoted trifluoromethylthiolation of arenediazonium salts with AgSCF3

An efficient method for trifluoromethylthiolation of arenediazonium salts has been developed in mild conditions with a stable and convenient AgSCF3. It provides a straightforward and convenient way for the synthesis of trifluoromethylthiolated compound from diazonium salts in moderate to good yields.