332-26-3

Basic information

• Product Name: 4-(Trifluoromethylthio)benzonitrile
• Synonyms: P-CYANOPHENYL TRIFLUOROMETHYL SULFIDE;4-(TRIFLUOROMETHYLTHIO)BENZONITRILE;4-TRIFLUOMETHYLTHIO BENZONITRILE;4-(Trifluoromethylthio)benzonitrile 98%;4-(Trifluoromethylthio)benzonitrile98%;4-[(trifluoroMethyl)sulfanyl]benzonitrile;4-[(Trifluoromethyl)sulphanyl]benzonitrile, 4-Cyanophenyl trifluoromethyl sulphide;4-(Trifluoromethylthio)benzonitrile ,p-(Trifluoromethylthio)benzonitrile
• CAS NO: 332-26-3
• Molecular Formula: C₈H₄F₃NS
• Molecular Weight: 203.18
• Product Categories: Aromatic Nitriles;Building Blocks;C8 to C9;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 332-26-3.mol

Chemical Properties

• Melting Point: 39-43 °C(lit.)
• Boiling Point: 187.643 °C at 760 mmHg
• Flash Point: 67.285 °C
• Appearance: /
• Density: 1.387 g/cm³
• Vapor Pressure: 0.29mmHg at 25°C
• Refractive Index: 1.535
• Sensitive: Stench
• CAS DataBase Reference: 4-(Trifluoromethylthio)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trifluoromethylthio)benzonitrile(332-26-3)
• EPA Substance Registry System: 4-(Trifluoromethylthio)benzonitrile(332-26-3)

Safety Data

• Hazard Codes: T
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• WGK Germany: 3
• Hazardous Substances Data: 332-26-3(Hazardous Substances Data)

Usage

Uses

Used in Research and Development:
4-(Trifluoromethylthio)benzonitrile is used as a reagent in research settings for the synthesis of complex organic molecules. Its unique trifluoromethylthio group provides specific reactivity and properties that are valuable in the development of new chemical entities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(Trifluoromethylthio)benzonitrile is used as an intermediate in the synthesis of pharmaceutical compounds. Its presence in these molecules can contribute to enhanced biological activity and selectivity, which is crucial for the development of effective drugs.
Used in Chemical Synthesis:
4-(Trifluoromethylthio)benzonitrile is utilized as an intermediate in various chemical synthesis processes. Its aromatic structure and trifluoromethylthio group offer unique opportunities for the creation of novel chemical entities with potential applications in various fields.
Used in Material Science:
In material science, 4-(Trifluoromethylthio)benzonitrile may be used as a component in the development of new materials with specific properties. Its incorporation into polymers or other materials could lead to advancements in areas such as electronics, coatings, or specialty chemicals.

InChI:InChI=1/C8H8BrF/c9-6-5-7-1-3-8(10)4-2-7/h1-4H,5-6H2

Upstream product

• 1413732-47-4 (2,2'-bipyride-kN₁,kN₁')(1,1,1-trifluoromethanethiolato-kS)-copper 
• 126747-14-6 4-cyanophenylboronic acid 
• 3058-39-7 4-iodobenzonitrile 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 56456-52-1 (4-((trifluoromethyl)thio)phenyl)methanol 
• 811-68-7 silver(I) trifluoromethanethiolate 
• 15898-42-7 sodium 4-cyanobenzenesulfinate 
• 2926-29-6 Langlois reagent 
• 873-74-5 4-Aminobenzonitrile 
• 438189-97-0 S-(4-cyanophenyl) 4-cyanobenzenesulfonothioate 
• 767-00-0 4-cyanophenol 
• 719-98-2 N-((trifluoromethyl)thio)isoindoline-1,3-dione 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 

Downstream Products

• 131786-66-8 2-<4-<(trifluoromethyl)thio>phenyl>-4-hydroxy-5-methylthiazole 
• 4021-50-5 4-(trifluoromethylthio)benzaldehyde 
• 1347581-55-8 1-(3-{[5-Methyl-3-(3-{4-[(trifluoromethyl)sulphanyl]phenyl}-1,2,4-oxadiazol-5-yl)-1H-pyrazol-1-yl]methyl}phenyl)piperidin-4-ol 
• 1346690-03-6 5-(5-Methyl-1H-pyrazol-3-yl)-3-{4-[(trifluoromethyl)sulphanyl]phenyl}-1,2,4-oxadiazole 
• 1347581-78-5 5-[1-(3-Bromobenzyl)-5-methyl-1H-pyrazol-3-yl]-3-{4-[(trifluoromethyl)sulphanyl]phenyl}-1,2,4-oxadiazole 
• 1085453-81-1 N'-hydroxy-4-[(trifluoromethyl)sulphanyl]benzenecarboximidamide 
• 1027083-94-8 (2E,4E)-5-(4-Trifluoromethylsulfanyl-phenyl)-penta-2,4-dien-1-ol 
• 183801-35-6 (2E,4E)-5-(4-Trifluoromethylsulfanyl-phenyl)-penta-2,4-dienal 
• 312-21-0 4-[(trifluoromethyl)sulfonyl] benzonitrile 
• 330-17-6 4-(trifluoromethylthio)benzoic acid 

Relevant articles and documents

A “universal” catalyst for aerobic oxidations to synthesize (hetero)aromatic aldehydes, ketones, esters, acids, nitriles, and amides

Functionalized (hetero)aromatic compounds are indispensable chemicals widely used in basic and applied sciences. Among these, especially aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides represent valuable fine and bulk chemicals, which are used in chemical, pharmaceutical, agrochemical, and material industries. For their synthesis, catalytic aerobic oxidation of alcohols constitutes a green, sustainable, and cost-effective process, which should ideally make use of active and selective 3D metals. Here, we report the preparation of graphitic layers encapsulated in Co-nanoparticles by pyrolysis of cobalt-piperazine-tartaric acid complex on carbon as a most general oxidation catalyst. This unique material allows for the synthesis of simple, functionalized, and structurally diverse (hetero)aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides from alcohols in excellent yields in the presence of air.

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.

Transition-Metal-Free Synthesis of Aryl Trifluoromethyl Thioethers through Indirect Trifluoromethylthiolation of Sodium Arylsulfinate with TMSCF3

Herein, we report an indirect trifluoromethylthiolation of sodium arylsulfinates. This transition-metal-free reaction significantly provides an environmentally friendly and practical synthetic method for aryl trifluoromethyl thioethers using commercial Ruppert-Prakash reagent TMSCF3. This approach is also a potential alternative to the current industrial production method owing to facile substrates, excellent functional group compatibility, and operational simplicity.

Metal-Free Trifluoromethylthiolation of Arylazo Sulfones

A visible-light-driven protocol for the synthesis of aryl trifluoromethyl thioethers under photocatalyst- and metal-free conditions has been pursued. The procedure exploits the peculiar properties of arylazo sulfones (having electron-rich or electron-poor substituents on the (hetero)aromatic ring) as photochemical precursors of aryl radicals and S-trifluoromethyl arylsulfonothioates as easy-to-handle trifluoromethylthiolating agents.

Method for synthesizing aromatic trifluoromethylthio compound

The invention discloses a method for synthesizing an aromatic trifluoromethylthio compound. The method comprises the following steps: reacting sodium trifluoromethanesulfinate with Chlorodiphenyl phosphine at room temperature; after reacting for a period of time, sequentially adding an aniline compound and tert-butyl nitrite, fully reacting at 70 +/-5 DEG C by taking CuSO4 as a catalyst and acetonitrile as a solvent, cooling to room temperature after the reaction is finished, extracting, carrying out reduced pressure distillation, and carrying out column chromatography separation and purification on the reaction mixture to obtain the aromatic trifluoromethylthio compound. The method is simple and safe in process operation and high in reaction conversion rate, the used raw materials are economical and practical, few three wastes are generated, and no extra organic solvent needs to be treated.

Perfluoroalkylation of Thiosulfonates: Synthesis of Perfluoroalkyl Sulfides

A practical synthesis of perfluoroalkyl sulfides is described. The method employs stable and readily accessible thiosulfonates as new electrophiles with commercial nucleophilic perfluoroalkylating reagents. The mild reaction conditions allow access to a wide variety of both aryl- and alkyl-substituted perfluoroalkyl sulfides amenable to pharmaceutical development. Furthermore, the reaction operation is straightforward, odorless, does not produce toxic wastes, and, therefore should appeal to practitioners in industrial-scale productions.

Visible-Light-Mediated Synthesis of Trifluoromethylthiolated Arenes

The visible-light-mediated synthesis of trifluoromethylthiolated arenes in the presence of ruthenium-based photocatayst under mild reaction conditions is reported. The trifluoromethylthiolated arenes are obtained using the shelf-stable reagent trifluoromethyl toluenethiosulfonate at room temperature. The reaction proceeds selectively and does not require the presence of any additive. A mechanism is proposed based on the obtained results of EPR as well as luminescence.

A process for converting substituted phenyl diazonium salts into [(trifluoromethyl)thio]benzene

The invention discloses a synthetic method of [(trifluoromethyl)thio]benzene compounds, particularly a method for converting substituted phenyl diazonium salts into [(trifluoromethyl)thio]benzene. Themethod comprises the following steps: under white light

Method for producing substituted [(trifluoromethyl)thio]benzene from substituted aniline

The invention discloses a synthetic method of [(trifluoromethyl)thio]benzene compounds, particularly a method for preparing substituted [(trifluoromethyl)thio]benzene from substituted aniline. The method comprises the following steps: adding aromatic amine, a catalyst, tert-butyl nitrite and p-toluenesulfonic acid hydrate into a solvent; stirring the mixture for at least 5 minutes at the room temperature of 20-25 DEG C; then adding S-trifluoromethyl-4-methoxybenzenesulfonyl sulfate, and uniformly stirring the mixture; reacting the mixture under white light irradiation at the room temperature of 20-25 DEG C; determining the reaction ending time through spotting detection; after the reaction is finished, adding water for extraction; performing separation to obtain a liquid organic phase; drying the liquid organic phase with anhydrous Na2SO4; then removing a solvent; and performing rapid separation with column chromatography to obtain a [(trifluoromethyl)thio]benzene compound. The preparation method is mild in reaction condition, free of high-temperature and high-pressure reaction, safe in reaction condition and suitable for large-scale production and development.

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.