403-66-7

Basic information

• Product Name: 4-(Trifluoromethylthio)nitrobenzene
• Synonyms: (4-Nitrophenyl)(trifluoroMethyl)sulfane;p-nitrophenyl trifluoromethyl sulfide;4-(TRIFLUOROMETHYLTHIO)NITROBENZENE;4-Nitrophenyl trifluoromethyl sulphide;1-NITRO-4-TRIFLUOROMETHYLSULFANYL-BENZENE;4-(TRIFLUOROMETHYLTHIO)NITROBENZENE,98%
• CAS NO: 403-66-7
• Molecular Formula: C₇H₄F₃NO₂S
• Molecular Weight: 223.17
• Mol File: 403-66-7.mol

Chemical Properties

• Boiling Point: 201.4 °C at 760 mmHg
• Flash Point: 75.6 °C
• Appearance: /
• Density: 1.5 g/cm³
• CAS DataBase Reference: 4-(Trifluoromethylthio)nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trifluoromethylthio)nitrobenzene(403-66-7)
• EPA Substance Registry System: 4-(Trifluoromethylthio)nitrobenzene(403-66-7)

Safety Data

• Hazardous Substances Data: 403-66-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 6677, 1992 DOI: 10.1016/S0040-4039(00)61016-X

Upstream product

• 2314-97-8 iodotrifluoromethane 
• 1849-36-1 para-nitrobenzenethiol 
• 75-63-8 Bromotrifluoromethane 
• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 75-46-7 trifluoromethan 
• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 100-01-6 4-nitro-aniline 
• 887144-97-0 Togni's reagent 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 1092380-21-6 S-(trifluoromethyl)-4-nitrophenylphenylsulfonium tetrafluoroborate 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 811-68-7 silver(I) trifluoromethanethiolate 
• 2926-29-6 Langlois reagent 

Downstream Products

• 95970-31-3 C₈H₄F₆N₂O₄S₂ 
• 100-17-4 para-methoxynitrobenzene 
• 394-60-5 1-nitro-4-[(R,S)-(trifluoromethyl)sulfinyl]benzene 
• 713-66-6 4-nitrophenyl trichloromethylsulfide 
• 16936-65-5 Tribrommethyl-(4-nitrophenyl)-sulfid 
• 99479-65-9 2,6-dichloro-4-trifluoromethylthio-aniline 
• 708-67-8 4-aminophenyl trifluoromethylsulfoxide 
• 326-45-4 SKA-19 
• 95448-39-8 imino(4-nitrophenyl)(trifluoromethyl)-λ⁶-sulfanone 
• 372-16-7 thioorthocarbonotrifluoridic acid 4-amino-phenyl ester 
• 1948-05-6 (3-Amino-phenyl)-trifluormethyl-sulfoxid 
• 942-39-2 1-fluoro-4-((trifluoromethyl)sulfinyl)benzene 
• 1948-06-7 <3-Nitro-phenyl>-trifluormethyl-sulfoxid 
• 703-18-4 phenyl trifluoromethyl sulfoxide 

Relevant articles and documents

Method for synthesizing nitro (hetero) aromatic hydrocarbon

The invention discloses a method for synthesizing nitro (hetero) aromatic hydrocarbon, and belongs to the field of organic synthesis. According to the method, simple (hetero) aromatic hydrocarbon is taken as an initial raw material and is stirred and reacted in an organic solvent at 40-100 DEG C under the action of a nitration reagent, a lewis acid catalyst and protective gas, and nitro (hetero) aromatic hydrocarbon can be obtained. The method provided by the invention has the advantages of cheap and easily available raw materials, mild reaction conditions, simple preparation process, good chemical selectivity, wide substrate application range, easy amplification and the like, has great application potential, and lays a good foundation for industrial production.

Kilogram-Scale Preparation of the Easily Available, Low-Cost Electrophilic Trifluomethylating Reagent YlideFluor

A kilogram-scale process for the preparation of a potentially broadly applicable electrophilic trifluoromethylating reagent, (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (YlideFluor), was reported. The reagent was prepared in three steps from a cheap, commercially available starting material, and the price of the reagent is estimated to be as low as $1.5/g. Application of the reagent in the preparation of trifluoromethylated derivatives of two drug molecules in the gram scale was demonstrated.

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.

Rational Design and Development of Low-Price, Scalable, Shelf-Stable and Broadly Applicable Electrophilic Sulfonium Ylide-Based Trifluoromethylating Reagents

The development of two highly reactive electrophilic trifluoromethylating reagents (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (1g) and (trifluoromethyl)(3-chlorophenyl)bis(carbomethoxy)methylide (1j) through structure-activity study was described. Under mild conditions, reagent 1g reacted with β-ketoesters and silyl enol ethers to give α-trifluoromethylated-β-ketoesters or α-trifluoromethylated ketones in high yields. In addition, reagent 1g could serve as a trifluoromethyl radical for a variety of trifluoromethylative transformations under visible light irradiation, including radical trifluoromethylation of electron-rich indoles and pyrroles and sodium aryl sulfinates as well as trifluoromethylative difunctionalization with styrene derivatives. On the other hand, as a complimentary, under reductive coupling conditions, reagent 1j reacted with a variety of (hetero)aryl iodides for the formation of trifluoromethylated (hetero)arenes.

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The invention provides a synthesis method of an aryltrifluoromethyl sulfide compound, which comprises the following steps: mixing aryl halide, silver trifluoromethane mercaptide, a copper salt catalyst, a nitrogen-containing organic ligand and an organic solvent, and stirring at 20-120 DEG C to react for 1-60 hours, so that after the reaction is finished, the aryl trifluoromethyl thioether compound is generated. The method has the advantages of cheap and easily available raw materials, mild reaction conditions, good substrate universality, high yield, suitability for industrial application and the like.

Electrochemical Trifluoromethylation of Thiophenols with Sodium Trifluoromethanesulfinate

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Enhancement of Benzothiazoles as Pteridine Reductase-1 Inhibitors for the Treatment of Trypanosomatidic Infections

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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.