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

Description

Trifluoromethylthiobenzene, also known as Phenyl trifluoromethyl sulfide, is an organic compound that features a benzene ring with a trifluoromethylthio group attached to it. Trifluoromethylthiobenzene is known for its unique chemical properties and reactivity, making it a valuable intermediate in the synthesis of various organic and pharmaceutical compounds.

Uses

Used in Chemical Synthesis:
Trifluoromethylthiobenzene is used as an intermediate in the preparation of various organic compounds, such as sulfoxides, dithiane dioxide, and dithiolane dioxide. It is involved in iron-catalyzed oxidation reactions of sulfides, dithiane, or dithiolane with hydrogen peroxide, which allows for the formation of these valuable products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, trifluoromethylthiobenzene is used as a building block for the synthesis of bioactive molecules and drug candidates. Its unique trifluoromethylthio group can impart specific properties to the final drug molecule, such as increased lipophilicity, metabolic stability, and binding affinity to target proteins.
Used in the Synthesis of Fluorinated Compounds:
Trifluoromethylthiobenzene is also used in the synthesis of fluorinated compounds, such as trifluoroand difluoromethylsilanes. These compounds are obtained through reductive coupling reactions of fluoromethyl sulfones, sulfoxides, and sulfides with chlorosilanes. The resulting fluorinated compounds have potential applications in various fields, including materials science, agrochemistry, and pharmaceuticals.
Used in the Preparation of Benzophenone Hydrazone Derivatives:
Furthermore, trifluoromethylthiobenzene is utilized in the preparation of benzophenone hydrazone derivatives. These derivatives are important in organic chemistry as they can act as precursors to various heterocyclic compounds and have potential applications in the synthesis of pharmaceuticals, dyes, and other organic compounds.

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

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 
• 701-65-5 (trichloromethylthio)benzene 
• 421-17-0 Trifluoromethylsulfenyl chloride 
• 372-16-7 thioorthocarbonotrifluoridic acid 4-amino-phenyl ester 
• 2314-97-8 iodotrifluoromethane 
• 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 
• 3111-52-2 potassium thiophenolate 
• 372-64-5 Bis(trifluoromethyl)disulfid 

Downstream Products

• 426-58-4 (trifluoromethylsulfonyl)benzene 
• 366-96-1 4-trifluoromethylsulfanyl-m-phenylenediamine 
• 22172-65-2 3-phenyl-5-trifluoromethylsulfanyl-benzo[c]isoxazole 
• 95970-27-7 phenyl N-(trifluoromethanesulfonyl) trifluoromethyl sulfilimine 
• 703-18-4 phenyl trifluoromethyl sulfoxide 
• 87996-58-5 trifluoromethylthio-4 fluoro-4' benzophenone 
• 701-65-5 (trichloromethylthio)benzene 
• 16936-63-3 Tribrommethyl-phenyl-sulfid 
• 70350-12-8 difluoro(phenyl)(trifluoromethyl)-λ⁴-sulfane 
• 191084-78-3 (4-methoxyphenyl)[2-(2-phenyl-1,1,1-trifluoroethyl)] amine 
• 144434-16-2 Phenyl-(2,2,2-trifluoro-1-furan-2-yl-ethyl)-amine 

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.