65325-64-6

Upstream product

• 623-13-2 4-methylphenyl methylsulfide 
• 34125-84-3 chloromethyl p-tolyl sulfide 
• 934-72-5 Methyl p-tolyl sulfoxide 
• 373-53-5 fluoroiodomethane 
• 106-45-6 para-thiocresol 

Downstream Products

• 65325-67-9 1-((fluoromethyl)sulfinyl)-4-methylbenzene 
• 115909-68-7 1-((fluoromethyl)sulfonyl)-4-methylbenzene 
• 1374153-68-0 (fluoromethyl)(2,3,4,5-tetramethylphenyl)(p-tolyl)sulfonium triflate 
• 1451993-20-6 5-amino-N-(4-((fluoromethyl)sulfonyl)benzyl)-3,4-dimethylthieno[2,3-c]pyridazine-6-carboxamide 
• 1394022-49-1 1-(bromomethyl)-4-((fluoromethyl)sulfonyl)benzene 
• 1451998-53-0 1-(azidomethyl)-4-((fluoromethyl)sulfonyl)benzene 
• 1394022-78-6 (4-((fluoromethyl)sulfonyl)phenyl)methanamine 
• 491837-01-5 (E)-1-fluoro-3-phenyl-1-tosyl-1-propene 

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

Direct and Chemoselective Electrophilic Monofluoromethylation of Heteroatoms (O-, S-, N-, P-, Se-) with Fluoroiodomethane

The commercially available fluoroiodomethane represents a valuable and effective electrophilic source for transferring the CH2F unit to a series of heteroatom-centered nucleophiles under mild basic conditions. The excellent manipulability offered by its liquid physical state (bp 53.4 °C) enables practical and straightforward one-step nucleophilic substitutions to retain the chiral information embodied, thus allowing it to overcome de facto the requirement for fluoromethylating agents with no immediate access. The high-yielding methodology was successfully applied to a variety of nucleophiles including a series of drugs currently in the market.

SUBSTITUTED 5-AMINOTHIENO[2,3-C]PYRIDAZINE-6-CARBOXAMIDE ANALOGS AS POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4

In one aspect, the invention relates to substituted 5-aminothieno[2,3-c]pyridazine-6- carboxamide analogs, derivatives thereof, and related compounds, which are useful as positive allosteric modulators of the muscarinic acetylcholine receptor M4 (mAChR M4); synthesis methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with muscarinic acetylcholine receptor dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

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.

"Syn-effect" in the isomerization of (E)-α-fluorovinylic sulfones to the corresponding allylic sulfones under basic conditions

Toward the elucidation of the origin of the "syn-effect," the stereochemistry of the isomerization of (E)-α-fluorovinylic sulfones to the corresponding allylic sulfones under mild basic conditions was investigated. The ratio of (Z)-isomers of the resulting allylic sulfones decreased in the following order for the γ-substituents of the starting vinylic sulfones: F- > EtO- > CH3- > BnS- > CH3CH2- > (CH3)2CH- > (CH3)3C-, C6H5-. The fluorine atom showed the highest "syn-effect," which is herein defined as an effect that stabilizes the syn-conformation in the transition state against a steric or nonbonded repulsion; the rest of the series was in accord with previous results found in the conversion of a-unsubstituted (E)-vinylic sulfones to the corresponding allylic sulfones under similar conditions. These results were rationalized based on the σ→π* interaction.

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.

REACTIONS OF XENON DIFLUORIDE. PART 6. SOME REACTIONS OF PHOSPHORUS, ARSENIC AND IODINE COMPOUNDS

The reaction of XeF2 with some organo-phosphorus, -arsenic and -iodine compounds is described.The products were identified by fluorine nmr spectroscopy and the conditions under which fluorine exchange occurs were briefly investigated.Organoiodine(III) difluorides are suitable for the conversion of Ph2Te to Ph2TeF2; the decomposition of RIF2 liberates IF2 and fluoroalkane.