1678-43-9

Usage

Uses

Used in Organic Synthesis:
2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions, contributing to the formation of complex organic molecules.
Used in Pharmaceutical Research:
In pharmaceutical research, 2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE is utilized as a protecting group for the amino acid glycine, which is crucial for the synthesis of peptides and other bioactive molecules.
Used as a Precursor in Pharmaceutical Synthesis:
2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE serves as a precursor in the synthesis of various pharmaceuticals and biologically active compounds, highlighting its importance in drug development.
Used in the Development of Anti-Inflammatory Agents:
2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE is studied for its potential as an anti-inflammatory agent due to its role as an inhibitor of tumor necrosis factor production, indicating its possible use in treating inflammatory conditions.
Used in the Development of Anticancer Agents:
As a compound with potential pharmacological properties, 2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE is also being explored for its possible application in the development of anticancer agents, given its role in inhibiting specific pathways related to cancer progression.

InChI:InChI=1/C21H18O4S/c1-16-12-14-19(15-13-16)26(23,24)25-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17/h2-15,21H,1H3

Upstream product

• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 104-15-4 toluene-4-sulfonic acid 
• 451-40-1 phenyl benzyl ketone 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 5344-88-7 benzil monohydrazone 
• 75067-08-2 benzene 
• 98-59-9 p-toluenesulfonyl chloride 
• 13892-81-4 (Z)-1-(acetoxy)-1,2-diphenylethylene 
• 501-65-5 diphenyl acetylene 
• 24647-07-2 (E)-1-(acetoxy)-1,2-diphenylethylene 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 16106-44-8 potassium tosylate 

Downstream Products

• 3524-62-7 benzoin monomethyl ether 
• 104-15-4 toluene-4-sulfonic acid 
• 106991-84-8 2-(2-oxo-1,2-diphenyl-ethylsulfanyl)-1,2-diphenyl-ethanone 
• 1684-14-6 2,3-diphenylquinoxaline 

Relevant academic research and scientific papers

Evolution of N-Heterocycle-Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)-Mediated Oxidative Transformations

The reactivity of ortho-functionalized N-heterocycle-substituted iodoarenes (NHIAs) as organocatalysts in iodine(I/III)-mediated oxidations was systematically investigated in the α-tosyloxylation of ketones as the model reaction. During a systematic catalyst evolution, it was found that NH-triazoles and benzoxazoles have the most significant positive influence on the reactivity of the central iodine atom. A further catalyst improvement which focused on the substitution pattern of the arene revealed a remarkable ortho-effect. By introduction of an o-OMe group we were able to generate a novel NHIA with a so far unseen catalytic efficiency. This new catalyst is not only easy to synthesize but also enabled the α-tosyloxylation of carbonyl compounds at the lowest reported catalyst loading of only 1 mol%. Finally, the performance of this iodine(I) catalyst was successfully demonstrated in intramolecular oxidative couplings of biphenyls and oxidative rearrangements. (Figure presented.).

Enol Ester Synthesis via Cobalt-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Alkynes

A cobalt-catalyzed highly regio- and stereoselective hydro-oxycarbonylation of alkynes is reported. Both terminal and internal alkynes can react with carboxylic acids to afford enol esters in high yields. The catalyst generated from Co(BF4)2, tridentate phosphine ligand L5, and zinc in situ exhibits much higher reactivity than the corresponding cobalt/diphosphine complex.

Study of the Reactivity of [Hydroxy(tosyloxy)iodo]benzene Toward Enol Esters to Access α-Tosyloxy Ketones

The reactivity of enol esters toward [hydroxy(tosyloxy)iodo]benzene (HTIB) was assessed. These substrates were found to be rapidly converted in high yields to their corresponding α-tosyloxy ketones. This transformation demonstrates that these substrates can act as ketone surrogates. The scope of the method was investigated and aromatic, aliphatic, and cyclic enol esters were found to be suitable substrates for the reaction. The relative reactivity of a model substrate toward HTIB and m-CPBA was investigated, and it was found that the reaction could be performed under catalytic conditions.

An iodobenzene-catalysed domino route toward quinoxaline derivatives from simple ketones and o-phenylenediamines in one pot

An iodobenzene-catalysed domino route to quinoxalines from ketones and o-phenylenediamines in one pot has been developed. This transformation consisted of the generation of Koser's generation, α-tosyloxylation of ketones, nucleophilic substitution and intramolecular dehydration with o-phenylenediamines, and dehydrogenation. Website

Convenient synthesis of symmetrical diketosulfides from enolizable ketones using [hydroxy(tosyloxy)iodo]benzene and Na2S·9H20

An efficient method for the preparation of symmetrical diketosulfides of the type ArCOCH2SCH2COAr has been developed from the reaction of [hydroxy(tosyloxy)iodo]benzene with various acetophenones, followed by treatment with Na2

Enantioselective α-oxytosylation of ketones catalysed by iodoarenes

The α-oxytosylation of ketones catalysed by enantioen-riched iodoarenes using mCPBA as stoichiometric oxidant is reported to give useful synthetic intermediates in good yield and modest enantioselectivity. We believe this to be the first report of an enan

Hypervalent iodine in synthesis 80: One pot preparation of Se-(β-oxoalkyl) O,O-dialkyl selenophospates by reaction of ketones, [hydroxy(tosyloxy)iodo]benzene, and potassium O,O-dialkyl selenophosphates

One pot reactions of ketones, [hydroxy(tosyloxy)iodo]benzene and potassium O,O-dialkyl selenophosphates lead to the formation of the corresponding Se-(β-oxoalkyl)O,O-dialkyl selenophosphates under mild conditions and in good yield.

Highly Efficient α-Organosulfonyloxylation of Carbonyl Compounds under Microwave Irradiation

Iodobenzene diacetate and organosulfonic acid mediated reaction of various carbonyl compounds under solventless microwave irradiation provided α-organosulfonyloxy carbonyl compounds in high yields.

Reaction of Hydrazones with Methoxy(tosyloxy)iodobenzene (MTIB): Tosylate Formation under Oxidative Conditions

Treatment of aromatic hydrazones 1 containing electron-withdrawing, reduction sensitive substituents with MTIB gives the corresponding tosylates 2 in high yield. When the tosylate is particularly reactive the thermodynamically more stable methyl ether 3 is isolated. Analogous reactions with DAIB give acetates 4 in high yield. Dialkyl hydrazones give olefinic products (e.g. 7 and 8). (+)-Camphor hydrazone 1k with either MTIB or DAIB gives both camphene 12 (major product) and tricyclene 11 (minor product) suggesting that a carbene pathway accounts for some of the material formed in these oxidations.