312-20-9

Usage

Uses

Used in Pharmaceutical Industry:
1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its reactivity and ability to form different types of chemical bonds make it a valuable component in the production of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene is employed as an intermediate in the synthesis of agrochemicals, including pesticides and herbicides. Its role in creating effective and targeted agrochemicals helps to improve crop protection and yield.
Used in Organic Synthesis:
1-Bromo-4-[(trifluoromethyl)sulfonyl]benzene is used as a reagent in organic synthesis for the formation of carbon-carbon and carbon-nitrogen bonds. Its versatility in undergoing various chemical reactions, such as nucleophilic substitution and palladium-catalyzed cross-coupling, makes it an essential tool for chemists in constructing complex organic molecules for a wide range of applications.

InChI:InChI=1/C7H4BrF3O2S/c8-5-1-3-6(4-2-5)14(12,13)7(9,10)11/h1-4H

Upstream product

• 473-27-8 4-(trifluoromethanesulfonyl)aniline 
• 333-47-1 1-bromo-4-(trifluoromethyl)thiobenzene 
• 432-87-1 1-nitro-4-(trifluoromethylsulfonyl)benzene 
• 56456-52-1 (4-((trifluoromethyl)thio)phenyl)methanol 
• 219872-98-7 4-(trifluoromethylsulfonyl)benzyl alcohol 
• 25752-90-3 tert-butyl 4-bromophenyl sulfide 
• 75-46-7 trifluoromethan 
• 498-83-9 4-bromobenzenesulfonyl fluoride 
• 1242069-27-7 trifluoromethanesulfonic acid 4-bromo-2-trimethylsilanyl-phenyl ester 
• 2926-29-6 Langlois reagent 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 1961266-44-3 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 1203709-75-4 4-bromo-2,4,6-trimethyldiphenyliodonium trifluoromethanesulfonate 

Downstream Products

• 845616-92-4 1-(4-Trifluoromethanesulfonyl-phenyl)-piperazine 
• 63708-74-7 2-(4-trifluoromethylsulfonylphenylthio)benzoic acid 
• 1034822-28-0 tert-butyl 1'-{4-[(trifluoromethyl)sulfonyl]phenyl}-4,4'-bipiperidine-1-carboxylate 
• 360-01-0 1-iodo-4-((trifluoromethyl)sulfonyl)benzene 
• 64085-67-2 2-nitro-N-(4-((trifluoromethyl)sulfonyl)phenyl)aniline 

Relevant academic research and scientific papers

Synthesis and nicotinic acetylcholine receptor in vitro and in vivo pharmacological properties of 2′-fluoro-3′-(substituted phenyl)deschloroepibatidine analogues of 2′-fluoro-3′-(4- nitrophenyl)deschloroepibatidine

Herein, we report the synthesis and nicotinic acetylcholine receptor (nAChR) in vitro and in vivo pharmacological properties of 2′-fluoro- 3′-(substituted phenyl)deschloroepibatidines 5b-g, analogues of 3′-(4-nitrophenyl) compound 5a. All compounds had hi

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.

Enantioselective, Catalytic Vicinal Difluorination of Alkenes

The enantioselective, catalytic vicinal difluorination of alkenes is reported by II/IIII catalysis using a novel, C2-symmetric resorcinol derivative. Catalyst turnover via in situ generation of an ArIIIIF2 species is enabled by Selectfluor oxidation and addition of an inexpensive HF–amine complex. The HF:amine ratio employed in this process provides a handle for regioselective orthogonality as a function of Br?nsted acidity. Selectivity reversal from the 1,1-difluorination pathway (geminal) to the desired 1,2-difluorination (vicinal) is disclosed (>20:1 in both directions). Validation with electron deficient styrenes facilitates generation of chiral bioisosteres of the venerable CF3 unit that is pervasive in drug discovery (20 examples, up to 94:06 e.r.). An achiral variant of the reaction is also presented using p-TolI (up to >95 % yield).

Conformational Aspects in the Design of Inhibitors for Serine Hydroxymethyltransferase (SHMT): Biphenyl, Aryl Sulfonamide, and Aryl Sulfone Motifs

Malaria remains a major threat to mankind due to the perpetual emergence of resistance against marketed drugs. Twenty-one pyrazolopyran-based inhibitors bearing terminal biphenyl, aryl sulfonamide, or aryl sulfone motifs were synthesized and tested towards serine hydroxymethyltransferase (SHMT), a key enzyme of the folate cycle. The best ligands inhibited Plasmodium falciparum (Pf) and Arabidopsis thaliana (At) SHMT in target, as well as PfNF54 strains in cell-based assays in the low nanomolar range (18–56 nm). Seven co-crystal structures with P. vivax (Pv) SHMT were solved at 2.2–2.6 ? resolution. We observed an unprecedented influence of the torsion angle of ortho-substituted biphenyl moieties on cell-based efficacy. The peculiar lipophilic character of the sulfonyl moiety was highlighted in the complexes with aryl sulfonamide analogues, which bind in their preferred staggered orientation. The results are discussed within the context of conformational preferences in the ligands.

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

METHOD FOR PRODUCING TRIFLUOROMETHYLSULFONYL COMPOUND DERIVATIVE

PROBLEM TO BE SOLVED: To provide a method for producing a trifluoromethylsulfonyl compound derivative useful as synthetic intermediates for medicines and agrochemicals. SOLUTION: The method for producing a trifluoromethylsulfonyl compound derivative repre

Organocatalyzed Trifluoromethylation of Ketones and Sulfonyl Fluorides by Fluoroform under a Superbase System

Fluoroform (HCF3, HFC-23) is a side product in the manufacture of polytetrafluoroethylene (Teflon). Despite its attractive properties, taming HCF3 for trifluoromethylation is quite problematic owing to its low acidity and the labilit

Cu-catalyzed couplings of aryl iodonium salts with sodium trifluoromethanesulfinate

A convenient method for the preparation of aryl trifluoromethylsulfones from the reactions of diaryliodonium salts with sodium trifluoromethanesulfinate in the presence of copper catalysts is described. Cuprous oxide in DMF was found to be the optimal catalyst for the reaction. The reaction conditions are tolerant of various functional groups as well as of various counteranions of the iodonium salt. The synthetic utility of the process is demonstrated by performing the reaction on a preparative scale (88 g).