65325-67-9

Usage

Molecular Structure

A benzene ring with a methyl group and a fluoromethyl sulfinyl group attached to it

Chirality

Chiral molecule

Pharmaceutical Applications

Inhibits the enzyme l-amino acid decarboxylase, potentially useful in treating Parkinson's disease and other neurological disorders

Industrial Applications

Important intermediate in the synthesis of various pharmaceuticals and agrochemicals

Usage

Typically used as a building block in organic synthesis

Production Methods

Commonly produced using the Grignard reaction or other similar processes

Upstream product

• 65325-64-6 1-[(fluoromethyl)sulfanyl]-4-methylbenzene 
• 623-13-2 4-methylphenyl methylsulfide 
• 34125-84-3 chloromethyl p-tolyl sulfide 
• 672-78-6 methyl p-toluene sulfinate 
• 67-56-1 methanol 

Downstream Products

• 1374153-68-0 (fluoromethyl)(2,3,4,5-tetramethylphenyl)(p-tolyl)sulfonium triflate 

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

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.

Formation of enantiomerically pure 1-Fluorovinyl and 1-fluoromethyl sulfoxides

(Ss)-[Fluoro(p-tolylsulfinyl)methyl]diphenylphosphane oxide (2) was obtained with complete stereoselectivity from (fluoromethyl)diphenylphosphane oxide (3) and (S)-(-)-menthyl p-toluenesulfinate. 1-Fluorovinyl p-tolyl sulfoxides 1 were prepared in good yields by Horner-Wittig reaction of 2 with aldehydes, in excellent enantiomeric excess (ee). With ketones, yields were generally low. Stereoselectivity was high for aliphatic aldehydes, producing (Z) isomers, and for benzaldehydes, yielding the (E) isomers. A two-step, one-pot procedure for the conversion of 3 into 1 was also developed. Solvolysis of 2 provided the first route to enantiomerically pure (S)-1-(fluoromethyl)sulfinyl-4-methylbenzene (7).

Site-Selective Fluorination of Organic Compounds Using 1-Alkyl-4-fluoro-1,4-diazabicyclooctane Salts (Selectfluor Reagents)

The new "N-F"-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclooctane salts (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclooctane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates.These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing α-H atoms, certain carbanions, and mildly activated aromatic compounds.The products were obtained with good yields and regioselectivity under very mild reaction conditions.