383-10-8

Basic information

• Product Name: 1-Methyl-4-[(trifluoromethyl)sulfonyl]benzene
• Synonyms: (Trifluoromethyl)(4-methylphenyl) sulfone;1-Methyl-4-[(trifluoromethyl)sulfonyl]benzene
• CAS NO: 383-10-8
• Molecular Formula: C₈H₇F₃O₂S
• Molecular Weight: 224.2001896
• Mol File: 383-10-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-Methyl-4-[(trifluoromethyl)sulfonyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-4-[(trifluoromethyl)sulfonyl]benzene(383-10-8)
• EPA Substance Registry System: 1-Methyl-4-[(trifluoromethyl)sulfonyl]benzene(383-10-8)

Safety Data

• Hazardous Substances Data: 383-10-8(Hazardous Substances Data)

Upstream product

• 352-68-1 4-trifluoromethylthiotoluene 
• 455-16-3 p-toluenesulfonyl fluoride 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 84796-64-5 C₈H₇F₃N₂O₂S 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 536-57-2 p-toluene sulfinic acid 
• 2314-97-8 iodotrifluoromethane 
• 108-88-3 toluene 
• 887144-94-7 Togni's reagent II 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 123726-16-9 bis(4-methylphenyl)iodonium trifluoromethanesulfonate 
• 2926-29-6 Langlois reagent 
• 1204518-02-4 4-methylphenyl(2,4,6-trimethylphenyl)iodonium triflate 

Downstream Products

• 2192-27-0 (3-Nitro-4-methyl-phenyl)-trifluormethyl-sulfon 
• 118089-89-7 1-(bromomethyl)-4-(trifluoromethylsulfonyl)benzene 
• 194222-98-5 p-trifluoromethanesulfonylbenzyltriflone 
• 1933-61-5 <4-Carboxy-3-nitro-phenyl>-trifluormethyl-sulfon 

Relevant articles and documents

Nucleophilic trifluoromethylation of organic substrates using (trifluoromethyl)trimethylsilane in the presence of a fluoride anion. II. A convenient route to aryltrifluoromethyl-sulfides, - sulfoxides and -sulfones

Aryltrifluoromethyl-sulfides, -sulfoxides and -sulfones can be prepared by trifluoromethylation of the corresponding arylsulfenyl, -sulfinyl and -sulfonyl halides using (trifluoromethyl)trimethylsilane in the presence of fluoride sources, such as TASF . - Keywords: Nucleophilic trifluoromethylation; (Trifluoromethyl)trimethylsilane; Fluoride anion; Aryltrifluoromethylsulfides; Aryltrifluoromethylsulfoxides; Aryltrifluoromethylsulfones

Synthesis, Reactivity and Structural Properties of Trifluoromethylphosphoranides

Phosphoranides are interesting hypervalent species which serve as model compounds for intermediates or transition states in nucleophilic substitution reactions at trivalent phosphorus substrates. Herein, the syntheses and properties of stable trifluoromet

Practical and efficient synthesis of aryl trifluoromethyl sulfones from arylsulfonyl chlorides with Umemoto's reagent II

A practical and efficient method for the synthesis of aryl trifluoromethyl sulfones has been developed by a tandem reaction of arylsulfonyl chlorides with Umemoto's reagent II. The advantageous features of this method are simple operation, mild reaction conditions, wide scope of substrates, high yield of products, and easy scalability.

Bifluoride Ion Mediated SuFEx Trifluoromethylation of Sulfonyl Fluorides and Iminosulfur Oxydifluorides

SuFEx is a new-generation click chemistry transformation that exploits the unique properties of S?F bonds and their ability to undergo near-perfect reactions with nucleophiles. We report here the first SuFEx-based procedure for the efficient synthesis of pharmaceutically important triflones and bis(trifluoromethyl)sulfur oxyimines from sulfonyl fluorides and iminosulfur oxydifluorides, respectively. The new process involves rapid S?F exchange with trifluoromethyltrimethylsilane (TMSCF3) upon activation by potassium bifluoride in anhydrous DMSO. The reaction tolerates a wide selection of substrates and proceeds under mild conditions without need for chromatographic purification. A tentative mechanism is proposed involving nucleophilic displacement of S?F by the trifluoromethyl anion via a five-coordinate intermediate. The utility of late-stage SuFEx trifluoromethylation is demonstrated through the synthesis and selective anticancer properties of a bis(trifluoromethyl)sulfur oxyimine.

Synthesis of Aryl Triflones through the Trifluoromethanesulfonylation of Benzynes

The direct synthesis of aryl triflones, that is, trifluoromethanesulfonyl arenes, was achieved through the trifluoromethanesulfonylation of benzynes. The trifluoromethanesulfonyl group, one of the fluorinated functional groups, is a highly electron-negative and mild lipophilic substituent. Aryl triflones have high potential in the synthesis of bioactive compounds and specialty materials. The treatment of 2-(trimethylsilyl)aryl trifluoromethanesulfonates with cesium fluoride in the presence of 15-crown-5 generated benzynes, which reacted with sodium trifluoromethanesulfinate followed by protonation with tBuOH under heating conditions, provided aryl triflones in moderated to good yields. Both symmetrical and unsymmetrical triflones were nicely accessed under the same reaction conditions. Interestingly, the trifluoromethanesulfonylation of unsymmetrical benzyne precursors proceeded smoothly to furnish corresponding aryl triflones in good yields with good to high regioselectivities. The balance of polarization of electric charge as well as steric hindrance of the benzyne intermediates are central factors to control the outcome of regioselectivity.

Copper-Mediated Di- and Monofluoromethanesulfonylation of Arenediazonium Tetrafluoroborates: Probing the Fluorine Effect

A copper-mediated di- and monofluoromethanesulfonylation of arenediazonium tetrafluoroborates using di- and monofluoromethanesulfinate reagents provides aryl difluoromethyl (or monofluoromethyl) sulfones in good yields. It was found that the relative reactivity of these sodium fluoroalkanesulfinates in the present reactions decreases in the following order: CH2FSO2Na > CF2HSO2Na > CF3SO2Na.

A method of manufacturing a benzene derivative (trifluoromethylsulfonyl)

PROBLEM TO BE SOLVED: To provide a method for producing a (trifluoromethylsulfonyl)benzene derivative which is useful as a medicine, an agricultural chemical, a functional material and a production intermediate thereof. SOLUTION: In this method, a (trifluoromethylsulfonyl)benzene derivative is produced by reacting diaryliodonium salt represented by general formula (1) with trifluoromethanesulfinic acid salt in the presence of a copper (I) salt. (In the formula, R1, R2, R3, R4, R5, R6, R7, R8, R9and R10each independently represents a hydrogen atom, a 1-6C alkyl group, a 1-6C haloalkyl group, a 1-6C alkoxy group, a 2-6C acyl group, (1-5C alkoxy)carbonyl group, a nitro group, a cyano group, a chlorine atom or a bromine atom). COPYRIGHT: (C)2013,JPOandINPIT

Copper-catalyzed trifluoromethylation of arylsulfinate salts using an electrophilic trifluoromethylation reagent

A copper-catalyzed method for the trifluoromethylation of arylsulfinates with Togni's reagent has been developed, affording aryltrifluoromethylsulfones in moderate to good yields. A wide range of functional groups in arylsulfinates are compatible with the

A novel synthesis of deactivated benzylic triflones

A two-step synthesis of benzylic triflones, based on the reaction of 2.4.6-trisubstituted phenyl halides 3a-f with the anion of ethyl (trifluoromethanesulfonyl)acetate 1 followed by a decarboxylation reaction, is reported. The structural assignments are s

A convenient route to aryl trifluoromethyl sulfones by fluoride-catalyzed cross-coupling of arenesulfonyl fluorides with (trifluoromethyl)trimethylsilane and (trifluoromethyl)trimethylstannane

Trifluoromethylsulfonyl substituted aromatic compounds 3a-d are prepared from the corresponding sulfonyl fluorides 1a-d by reacting with (trifluoromethyl)trimethylsilane (or-stannane) in the presence of a base under mild conditions in high yields.