5000-44-2

Usage

Uses

Used in Chemical Synthesis:
BENZENESULFONYLACETONE is used as a key intermediate in the synthesis of various organic compounds, particularly for the production of 2,3,5-trisubstituted furans. Its unique chemical properties make it a valuable component in creating complex molecular structures with potential applications in pharmaceuticals, materials science, and other industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BENZENESULFONYLACETONE is used as a building block for the development of new drugs. Its ability to form various derivatives and participate in different chemical reactions allows researchers to create novel compounds with potential therapeutic properties.
Used in Materials Science:
BENZENESULFONYLACETONE is also utilized in the field of materials science, where it can be employed to synthesize new materials with specific properties. These materials may have applications in areas such as electronics, coatings, and adhesives, where unique chemical and physical characteristics are desired.

InChI:InChI=1/C9H10O3S/c1-8(10)7-13(11,12)9-5-3-2-4-6-9/h2-6H,7H2,1H3

Upstream product

• 5042-53-5 1-(phenylsulfanyl)acetone 
• 64-17-5 ethanol 
• 873-55-2 sodium benzenesulfonate 
• 78-95-5 chloroacetone 
• 3112-85-4 methylphenylsulfonate 
• 141-78-6 ethyl acetate 
• 7148-07-4 1-pyrrolidinocyclopent-1-ene 
• 2525-42-0 phenylsulfonylpropa-1,2-diene 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 14092-11-6 1-pyrrolidino-1-cycloheptene 
• 16675-55-1 1,2,5,6-tetrahydro-1-methyl-4-pyrrolidinopyridine 
• 39716-23-9 1-(4-methylcyclohex-1-en-1-yl)pyrrolidine 
• 7007-34-3 1-(3,4-dihydro-1-naphthalenyl)pyrrolidine 
• 2525-41-9 1-(phenylsulfonyl)propyne 

Downstream Products

• 679002-59-6 2-methyl-3-(phenylsulfonyl)quinoline 
• 15296-86-3 1-(phenylsulfanyl)methyl phenyl sulfone 
• 858835-74-2 1-benzenesulfonyl-1-methylsulfanyl-acetone 
• 119698-13-4 bis-(1-benzenesulfonyl-acetonyl)-dibutyl stannane 
• 343348-18-5 benzenesulfonyl-acetone oxime 
• 60156-13-0 1-Bromo-3-phenylsulfonyl-propan-2-one 
• 859074-96-7 1-benzenesulfonyl-1-p-tolylsulfanyl-acetone 
• 67-63-0 isopropyl alcohol 
• 618-41-7 Benzenesulfinic acid 
• 98-11-3 benzenesulfonic acid 
• 71512-27-1 3-Phenylsulfonyl-hexanon-⁽³⁾ 
• 29943-19-9 3-Benzenesulfonyl-6-ethylsulfanyl-hexan-2-one 
• 68276-72-2 1-(phenylsulfonyl)-2-propanol 
• 38488-21-0 1-(benzenesulfonyl)-1-diazopropan-2-one 

Relevant academic research and scientific papers

Iron(II)-induced degradation of antimalarial β-sulfonyl endoperoxides. Evidence for the generation of potentially cytotoxic carbocations

Reactions of antimalarial β-sulfonyl endoperoxides 9 and 10, which, like yingzhaosu A (2), derive from the 2,3-dioxabicyclo[3.3.1]nonane system 3, with iron(II) salts were studied. Product analysis of the iron(II)-induced degradations provided evidence fo

The facile synthesis of 1-benzoazepine derivatives via gold-catalyzed regioselective cycloisomerization reactions of N-(o-alkynylaryl)-N-vinyl sulfonamides

Gold-catalyzed, regioselective cycloisomerization of N-(o-alkynylaryl)-N-vinyl sulfonamides afforded high yields of 2-sulfonylmethyl-1-benzoazepine derivatives. This 7-endo-dig selective cyclization proceeds via the incorporation of an exocyclic double bond by a labile 1-benzoazepine intermediate. The cyclization substrates were assembled in two steps from readily available materials using Sonogashira coupling and a Cs2CO3-mediated formal vinylic substitution.

Iron-Catalyzed, Site-Selective Difluoromethylthiolation (-SCF2H) and Difluoromethylselenation (-SeCF2H) of Unactivated C(sp3)-H Bonds in N-Fluoroamides

The iron-catalyzed δ-C(sp3)-H bond difluoromethylthiolation and difluoromethylselenation of aliphatic amides with high site selectivity are reported. Essential to the success is the employment of an amide radical formed in situ to activate the inert C(sp3

A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent

A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.

Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones

A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the 'sulfonyl-azide-free' ('SAFE') protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.

Synthesis, Structure, and Chemical Transformations of 2-Chloroprop-2-en-1-yl Sulfones

A green approach was proposed for the synthesis of 2-chloroprop-2-en-1-yl sulfones in 47–94% yield. The molecular and crystal structures of 2-chloroprop-2-en-1-yl phenyl sulfone and 2-chloroprop-2-en-1-yl methyl sulfone were determined by X-ray analysis.

General [4 + 1] Cyclization Approach to Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides

A general [4 + 1] cyclization reaction of carbonyl nucleophiles with 2-iodomethylallyl peroxides, which function as unique electrophilic oxygen synthons, for the synthesis of a broad range of 2,2-disubstituted tetrahydrofurans is achieved under operationally simple conditions. The unprecedented asymmetric version of such reaction is also realized via chiral auxiliary-assisted cyclization, thus providing a distinct approach to access chiral tetrahydrofurans with high diastereoselectivities. The new method can be applied to the synthesis of core structure of posaconazole drug.

Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants

Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.

A DEVELOPING AGENT PRECURSOR FOR LASER MARKABLE COMPOSITIONS

The invention relates to novel laser markable compositions comprising developing agent precursors according to formula (I).

Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Br?nsted acids. NMR and DFT study of these cations and their reactions

In strong Br?nsted acids (CF3SO3H, FSO3H, D2SO4), (arysulfonyl)allenes (ArSO2-CR1=C=CR2R3) and (arylsulfinyl)allenes (ArSO-CR1=C=CR2R3) undergo cyclization into the corresponding stable 1,2-oxathiolium ions, which were studied by means of NMR and DFT calculations. Quenching of solutions of these cations with low nucleophilic media, aqueous HCl, leads to their deprotonation with a stereoselective formation of (arysulfonyl)butadienes (for instance, ArSO2-CR1=C-C(Me)=CH2, for R2 = R3 = Me, yields of 87-98%). Reactions of (arysulfonyl)allenes in the system TfOH (0.1 equiv)-HFIP (hexafluoropropan-2-ol) followed by hydrolysis give rise to allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3, yields of 78-99%). Reflux of solutions of (arysulfonyl)allenes in the presence of TfOH (1 equiv) in 1,2-dichlorobenzene leads to the cyclization into thiochromene 1,1-diox-ides in high yields. Under the action of TfOH or AlX3 (X = Cl, Br) followed by hydrolysis of reaction mixtures, (arylsulfinyl)allenes give allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3). Plausible reaction mechanisms have been proposed for all studied reactions.