65325-68-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
[(Fluoromethyl)sulfinyl]benzene is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used in Synthesis of Sulfoxide Derivatives:
It serves as a precursor for the preparation of sulfoxide derivatives, which have a range of industrial applications, including as catalysts, ligands, and building blocks in organic synthesis.
Used in Organic Chemistry as a Reagent:
[(Fluoromethyl)sulfinyl]benzene is utilized as a reagent in organic chemistry, particularly for the formation of carbon-carbon and carbon-heteroatom bonds, facilitating the creation of complex molecular structures.
Caution:
As a fluorinated compound, it is crucial to handle [(fluoromethyl)sulfinyl]benzene with care due to its potential toxicity and environmental impact, ensuring safe laboratory practices and proper disposal methods.

Upstream product

• 593-70-4 R₃₂ 
• 930-69-8 sodium thiophenolate 
• 100-68-5 methyl-phenyl-thioether 
• 108-98-5 thiophenol 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 7205-91-6 phenylthiomethyl chloride 
• 60839-94-3 2-fluoro-methylthiobenzene 

Downstream Products

• 92540-81-3 2-Benzenesulfinyl-3-phenyl-1-p-tolyl-aziridine 
• 92540-80-2 2-Benzenesulfinyl-1-(4-bromo-phenyl)-3-phenyl-aziridine 
• 92540-78-8 2-Benzenesulfinyl-3-(4-chloro-phenyl)-1-phenyl-aziridine 
• 60839-94-3 2-fluoro-methylthiobenzene 
• 1535-67-7 difluoromethyl phenyl sulfide 
• 81931-98-8 1-<(Difluoromethyl)thio>-4-methoxybenzene 
• 157336-59-9 1-Benzenesulfinyl-1-fluoro-3-phenyl-propan-2-ol 
• 85970-61-2 2-Benzenesulfinyl-2-fluoro-1-phenyl-ethanol 
• 147515-39-7 2-Benzenesulfinyl-1,3-diphenyl-aziridine 
• 209391-93-5 2-Benzenesulfinyl-2-fluoro-1,1-diphenyl-ethanol 
• 20808-12-2 fluoromethyl phenyl sulfone 
• 1280126-02-4 (fluoromethyl)(imino)(phenyl)-λ⁶-sulfanone 
• 1280126-07-9 N,N-(dimethylamino)-S-phenyl-S-monofluoromethyloxosulfonium trifluoromethanesulfonate 
• 1280126-09-1 N,N-(dimethylamino)-S-phenyl-S-monofluoromethyloxosulfonium hexafluorophosphate 

Relevant academic research and scientific papers

Optimized Monofluoromethylsulfonium Reagents for Fluoromethylene-Transfer Chemistry

An investigation of the properties and reactivity of fluoromethylsulfonium salts resulted in the redesign of the reagents for fluoromethylene transfer chemistry. The model reaction, fluorocyclopropanation of nitrostyrene, turned out to be a suitable platf

Novel process for synthesizing 2 -fluorocyclopropylamine with high selectivity and asymmetric synthesis

A novel highly selective asymmetric synthesis process of 2 -fluorocyclopropylamine (Structural I). The method provided by the invention uses 1 - fluorine -1 - benzene (propylene) sulfonyl methane and chiral epichlorohydrin to construct chiral cyclopropane under basic conditions, and a new synthetic route not only achieves a special cis-trans selectivity, but also has a highly specific stereoselectivity. The synthesis route is efficient, the reaction condition is mild, the method is suitable for large industrial production in a green environment, 2 -fluorocyclopropylamine production cost is greatly reduced.

Diastereoselective Monofluorocyclopropanation Using Fluoromethylsulfonium Salts

Diarylfluoromethylsulfonium salts, alternatives to freons or advanced fluorinated building blocks, are bench stable and easy-to-use sources of direct fluoromethylene (:CHF) transfer to alkenes. These salts enabled development of a trans-selective monofluorinated Johnson-Corey-Chaykovsky reaction with vinyl sulfones or vinyl sulfonamides to access synthetically challenging monofluorocyclopropane scaffolds. The described method offers rapid access to monofluorinated cyclopropane building blocks with further functionalization opportunities to deliver more complex synthetic targets diastereoselectively.

An electrophilic reagent for the synthesis of OCHFMe-containing molecules

Herein the synthesis of a novel and bench stable electrophilic reagent to construct the OCFHMe motif from O-nucleophiles has been described. This sulfonium salt, readily obtained in 5 steps, reacted with various phenols and alcohols. The resulting products, including complex molecules, were obtained in good yields. This reagent was also used for the functionalization of thiol derivatives.

Fluorinated trimethyllysine as a 19F NMR probe for trimethyllysine hydroxylase catalysis

Trimethyllysine hydroxylase (TMLH) catalyses C-3 hydroxylation of Nε-trimethyllysine in the first step of carnitine biosynthesis in humans. Studies on TMLH have been hampered by the lack of established chemical methods. We report that an N

Fluoromethylated derivatives of carnitine biosynthesis intermediates- synthesis and applications

A convenient method for the synthesis of fluoromethylated carnitine biosynthesis intermediates, i.e. fluorinated derivatives of γ- butyrobetaine and trimethyllysine, is described. The fluoromethylated probes were useful in both in vitro and cell based ass

ELECTROPHILIC REAGENTS FOR MONOHALOMETHYLATION,THEIR PREPARATION AND THEIR USES

The invention provides a compound of formula A, B, C or D, methods for making them, intermediates therefor, and their use in making organic biologically active compounds: (Formula (A)). Wherein: ? X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group ? R1, R2, R3, R4, R5, R6, R7, R8, R9, R1O are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino ? R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates ? Excluding the case when: X = F and R1= R2 = R3 = R4= R5 = H and R6 R8 = R9 = methyl, R10 = H and R11 = triflate or tetrafluoroborate; or (Formula (B)). Wherein: X = F, CI, Br, I, sulfonate esters, phosphate esters or other another leaving group; and R1, R2, R3, R4, R5 are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino and R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates; and R12 = resin, naphthalene or substituted naphthalene Excluding the case when: X = F and R1= R2 = R3 = R4= R5 = H and R6 = R7 = R8 = R9 = methyl, R10 = H and R11 = triflate or tetrafluoroborate and when X = F and R1= R2 = R3 = R4= R5 = H and R12 = poly(styrene-co- divinylbenzene) and R11 = triflate or tetrafluoroborate; or (Formula (C)). Wehrein ? X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group ? R13 = naphthalene or substituted naphthalene ? R6, R7, R8, R9, R10 are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alcoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino ? R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates: or (Formula (D)) X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group R13 = naphthalene or substituted naphthalene R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates carbonates R12 = resin, naphthalene or substituted naphthalene.

Inherent oxygen preference in enolate monofluoromethylation and a synthetic entry to monofluoromethyl ethers

Expect the unexpected: The self-stable salts 1, X=OTf, PF6, x=2, y=1, developed for electrophilic monofluoromethylation showed inherent selectivity for the O-alkylation of enolates, thus providing access to monofluoromethyl ethers, which are difficult to obtain by the direct electrophilic fluoromethylation of alcohols. Salt 1, X=BF4, x=0, y=3, in contrast leads to C-alkylated products.

Direct electrophilic monofluoromethylation

Monofluoromethyl derivatives of various nucleophiles have been synthesized using a new electrophilic monofluoromethylating reagent developed. The S-(monofluoromethyl)diarylsulfonium tetrafluoroborate has been shown to be effective for the introduction of an electrophilic monofluoromethyl group into C, S, O, N, and P nucleophiles. This methodology has been expanded for the synthesis of various biologically important compounds.

Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability

Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)2NSF3 (Deoxo-Fluor reagent), is a new deoxofluorinating agent that is much more thermally stable than DAST (C2H5)2NSF3 and its congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient sulfur atom of the trifluoride.