1678-43-9

Basic information

• Product Name: 2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE
• Synonyms: 2-PHENYL-2-TOSYLOXYACETOPHENONE;2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE;ALPHA-(P-TOLUENESULFONYLOXY)DEOXYBENZOIN;ALPHA-(TOSYLOXY)DEOXYBENZOIN;O-(P-TOLUENESULFONYL)BENZOIN;O-TOSYLBENZOIN;Benzoin 4-toluenesulfonate;2-Phenyl-2-tosyloxyacetophenone O-(p-Toluenesulfonyl)benzoin alpha-(p-Toluenesulfonyloxy)deoxybenzoin O-Tosylbenzoin alpha-(Tosyloxy)deoxybenzoin
• CAS NO: 1678-43-9
• Molecular Formula: C₂₁H₁₈O₄S
• Molecular Weight: 366.43
• Product Categories: Functional Materials;Photopolymerization Initiators
• Mol File: 1678-43-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 109 °C
• Boiling Point: 546.83°C at 760 mmHg
• Flash Point: 284.512°C
• Appearance: /
• Density: 1.258g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE(1678-43-9)
• EPA Substance Registry System: 2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE(1678-43-9)

Safety Data

• Hazardous Substances Data: 1678-43-9(Hazardous Substances Data)

Usage

General Description

2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE, also known as Tosylglycine, is a chemical compound with the molecular formula C22H21NO4S. It is a white to off-white crystalline powder that is commonly used as a reagent in organic synthesis and pharmaceutical research. 2-PHENYL-2-(P-TOLUENESULFONYLOXY)ACETOPHENONE is an acetylphenol derivative with a p-toluenesulfonyloxy group attached to the phenyl ring. It is primarily utilized as a protecting group for the amino acid glycine, and as a precursor in the synthesis of various pharmaceuticals and biologically active compounds. Tosylglycine has also been studied for its potential pharmacological properties, including its role as an inhibitor of tumor necrosis factor production and its anti-inflammatory effects.

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 articles and documents

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.).

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.

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