5535-52-4

Usage

Uses

Used in Pharmaceutical Industry:
P-Tolyl vinyl sulphone is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to modify and functionalize a wide range of organic compounds. Its strong electrophilic nature contributes to the development of new drugs and medications.
Used in Dye Synthesis:
P-Tolyl vinyl sulphone is used as a reactive component in the production of dyes, where its versatility in organic synthesis aids in creating a variety of colorants for different applications.
Used in Fine Chemicals Production:
In the field of fine chemicals, P-Tolyl vinyl sulphone is utilized as a building block for the creation of specialty chemicals, leveraging its reactivity to produce complex and high-value compounds.
Safety Precautions:
When handling P-Tolyl vinyl sulphone, it is essential to take safety precautions due to its potential to cause irritation to the skin, eyes, and respiratory system. Proper protective equipment and handling procedures should be followed to minimize risks associated with its use.

InChI:InChI=1/C18H16N4O2/c1-24-16-9-7-14(8-10-16)18(23)22-20-12-15-11-19-21-17(15)13-5-3-2-4-6-13/h2-12,20H,1H3,(H,22,23)/b15-12-

Upstream product

• 22381-54-0 2-(p-tolylsulfonyl)ethanol 
• 16336-54-2 p-tolyl vinyl sulfide 
• 22381-53-9 2-chloroethyl-p-toluenesulfonate 
• 121-44-8 triethylamine 
• 75-50-3 trimethylamine 
• 94460-95-4 2-(4-Tolyl-sulfonyl)-aethoxycarbonylanilin 
• 112471-53-1 2-tosylethyl 3-phenyl-2-propenoate 
• 112471-52-0 2-tosylethyl 3-phenylpropanoate 
• 71700-50-0 1-(tert-butyldimethylsilyloxy)-3-phenyl-2-propene 
• 74-85-1 ethene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 51849-04-8 α-Tosylaethyliden-triphenylphosphoran 
• 106-45-6 para-thiocresol 
• 351186-41-9 4-methyl-N-morpholin-4-ylbenzenesulfonamide 

Downstream Products

• 16236-65-0 1-[2-(toluene-4-sulfonyl)-ethyl]-piperidine 
• 22952-14-3 1,2-bis(p-tolylsulfonyl)ethane 
• 102011-25-6 3-nitro-1,5-bis-(toluene-4-sulfonyl)-pentane 
• 10154-80-0 3-[(4-methylbenzene)sulfonyl]propanenitrile 
• 99861-99-1 1-ethanesulfonyl-2-(toluene-4-sulfonyl)-ethane 
• 799260-84-7 (3-methyl-3-nitro-butyl)-p-tolyl sulfone 
• 101292-41-5 1-(4-chloro-2-methyl-phenylsulfanyl)-2-(toluene-4-sulfonyl)-ethane 
• 102449-40-1 ethyl-[2]naphthyl-[2-(toluene-4-sulfonyl)-ethyl]-amine 
• 112818-49-2 2-[2-(toluene-4-sulfonyl)-ethylsulfanyl]-anthraquinone 
• 102656-40-6 acetic acid-(4-{N-[2-(toluene-4-sulfonyl)-ethyl]-anilino}-anilide) 
• 112818-96-9 1-[2-(toluene-4-sulfonyl)-ethylsulfanyl]-anthraquinone 
• 65972-16-9 bis-[2-(toluene-4-sulfonyl)-ethyl]-sulfide 
• 59336-76-4 1,2-dibromo-1-p-tolylsulphonylethane 
• 35777-35-6 bis-[2-(toluene-4-sulfonyl)-ethyl]-amine 

Relevant academic research and scientific papers

Metal-free visible-light-promoted C(sp3)-H functionalization of aliphatic cyclic ethers using trace O2

Presented is a light-promoted C-C bond forming reaction yielding sulfone and phosphate derivatives at room temperature in the absence of metals or photoredox catalyst. This transformation proceeds in neat conditions through an auto-oxidation mechanism which is maintained through the leaching of trace amounts of O2 as sole green oxidant. This journal is

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.

Discovery of Unforeseen Energy-Transfer-Based Transformations Using a Combined Screening Approach

The discovery of novel (catalytic) transformations and mechanisms is commonly based on rational design. However, many discoveries have resulted directly from experimental serendipity. Building on this, we report a two-dimensional screening protocol, combining “mechanism-based” and “reaction-based” screening and its application to the field of visible light photocatalysis. To this end, two energy-transfer-based cycloaddition reactions could be realized: a notably endergonic energy transfer process allows for the dearomative cycloaddition of benzothiophenes and related heterocycles. Moreover, by sensitization of enone moieties, a [2+2]-cycloaddition to alkynes and an unexpected cycloaddition-rearrangement cascade were discovered. Advanced spectroscopic techniques (in particular transient absorption spectroscopy and pulse radiolysis) were utilized to investigate the underlying photophysical processes and gain insight into reaction kinetics. Combining these results with further mechanistic analysis can eventually turn out to be helpful upon knowledge-driven development of improved systems. Such screening approaches can thus provide complementary access toward novel and more efficient catalytic protocols. Driven by the continuous demand for more efficient and sustainable synthetic reactions, the discovery of novel (catalytic) reactivity patterns remains a major challenge of synthetic chemistry. The discovery of such processes is commonly based on rational design, i.e., the expansion of previously acquired knowledge to new substrate classes or reaction types. However, considering that many groundbreaking discoveries have resulted from experimental serendipity, serendipity-based screening methodologies have been developed as a complementary tool for the discovery of novel transformations. Particularly in the context of visible-light-mediated photocatalysis, which provides a powerful platform from which to develop new radical-based transformations, screening methodologies still have significant potential to discover new reactivity modes. How can catalytic reactions be discovered? Here, a two-dimensional screening strategy for reaction discovery is described. For this purpose, the investigation of single mechanistic steps is merged with combinatorial screening. As a showcase, application to the field of visible light photocatalysis allowed for the discovery of three unexpected cyclization reactions. Extensive mechanistic analysis by advanced spectroscopic and computational tools enabled insights into the underlying molecular processes. In particular, a significantly endergonic sensitization event could be discovered and substantiated by transient absorption spectroscopy.

Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts

A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.

Difluoro- and trifluoro diazoalkanes-complementary approaches in batch and flow and their application in cycloaddition reactions

Herein we report on applications of fluorinated diazoalkanes in cycloaddition reactions, with the emphasis on studying subtle differences between diverse fluorinated diazo compounds. These differences led to two major synthetic protocols in batch and flow that allow the safe and scalable synthesis of fluoroalkyl-, sulfone-substituted pyrazolines.

One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation

A palladium-catalysed aminosulfonylation process is used as the key-step in a one-pot, three-component sulfone synthesis. The process combines aryl-, heteroaryl- and alkenyl iodides with a sulfonyl unit and an electrophilic coupling fragment. The sulfonyl unit is delivered in the form of an aminosulfonamide, which then serves as a masked sulfinate. The sulfinate is combined, in situ, with an electrophilic coupling partner, such as a benzylic, allylic or alkyl halide, an electron-poor arene, or a cyclic epoxide, to provide the corresponding sulfone products in good to excellent yields. The mild reaction conditions and use of commercially available reaction components allows the easy preparation of a broad range of sulfones featuring a variety of functional groups. The process obviates the need to employ thiol starting materials, and oxidative operations.

Design, Synthesis, and Evaluation of 2-(arylsulfonyl)oxiranes as Cell-permeable Covalent Inhibitors of Protein Tyrosine Phosphatases

A structure-based design approach has been applied to develop 2-(arylsulfonyl)oxiranes as potential covalent inhibitors of protein tyrosine phosphatases. A detailed kinetic analysis of inactivation by these covalent inhibitors reveals that this class of compounds inhibits a panel of protein tyrosine phosphatases in a time- and dose-dependent manner, consistent with the covalent modification of the enzyme active site. An inactivation experiment in the presence of sodium arsenate, a known competitive inhibitor of protein tyrosine phosphatase, indicated that these inhibitors were active site bound. This finding is consistent with the mass spectrometric analysis of the covalently modified protein tyrosine phosphatase enzyme. Additional experiments indicated that these compounds remained inert toward other classes of arylphosphate-hydrolyzing enzymes, and alkaline and acid phosphatases. Cell-based experiments with human A549 lung cancer cell lines indicated that 2-(phenylsulfonyl)oxirane (1) caused an increase in intracellular pTyr levels in a dose-dependent manner thereby suggesting its cell-permeable nature. Taken together, the newly identified 2-(arylsulfonyl)oxiranyl moiety could serve as a novel chemotype for the development of activity-based probes and therapeutic agents against protein tyrosine phosphatase superfamily of enzymes.

CONTROLLED DRUG RELEASE FROM SOLID SUPPORTS

The invention relates to solid supports useful in medical applications that provide controlled release of drugs, such as peptides, nucleic acids and small molecules. The drugs are covalently coupled to the solid support through a linkage that releases the drug or a prodrug through controlled beta elimination.

CONTROLLED RELEASE FROM MACROMOLECULAR CONJUGATES

The invention relates to conjugates of macromolecular carriers and drugs comprising linkers that release the drug or a prodrug through rate-controlled beta-elimination, and methods of making and using the conjugates.

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 12. Extrusion of Ph3P from sulfonyl ylides and reactivity of the resulting sulfonyl carbenes

Twelve sulfonyl stabilised phosphorus ylides have been prepared and their behaviour upon flash vacuum pyrolysis at 600°C has been examined. Examples with an arylsulfonyl substituent undergo loss of Ph3PO to give intractable products but those with an arylmethylsulfonyl substituent separately lose Ph3P and SO2 to give products consistent with the intermediacy of sulfonyl carbenes. X-Ray structure determinations of one ylide from each series show a more significant P-O non-bonding interaction in the first case, providing some explanation for the different thermal reactivity.