98078-08-1

Basic information

• Product Name: 2-oxo-2-phenylethyl 2-phenylacetate
• Synonyms: 2-oxo-2-phenylethyl 2-phenylacetate
• CAS NO: 98078-08-1
• Molecular Weight: 254.285
• Mol File: 98078-08-1.mol

Chemical Properties

• CAS DataBase Reference: 2-oxo-2-phenylethyl 2-phenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-oxo-2-phenylethyl 2-phenylacetate(98078-08-1)
• EPA Substance Registry System: 2-oxo-2-phenylethyl 2-phenylacetate(98078-08-1)

Safety Data

• Hazardous Substances Data: 98078-08-1(Hazardous Substances Data)

Upstream product

• 103-82-2 phenylacetic acid 
• 70-11-1 α-bromoacetophenone 
• 94763-25-4 tri-n-butylstannyl phenylacetate 
• 114-70-5 sodium phenylacetate 
• 13005-36-2 potassium phenylacetate 
• 536-74-3 phenylacetylene 
• 582-24-1 1-phenyl-2-hydroxyethanone 

Downstream Products

• 5635-16-5 3,4-diphenyl-2(5H)-furanone 
• 103-82-2 phenylacetic acid 
• 98-86-2 acetophenone 
• 4808-48-4 2,3-diphenylmaleic anhydride 
• 114-70-5 sodium phenylacetate 
• 1044169-10-9 4-(5-oxo-4-phenyl-2,5-dihydro-furan-3-yl)-benzenesulfonyl chloride 

Relevant articles and documents

A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids

The Steglich esterification is a widely employed method for the formation of esters under mild conditions. A number of issues regarding the sustainability of this transformation have been identified, chiefly the use of hazardous carbodiimide coupling reagents in conjunction with solvents with considerable issues such as dichloromethane (DCM) and N,N-dimethylformamide (DMF). To overcome these issues, we have developed a solvent-reagent selection guide for the formation of esters via Steglich-type reactions with the aim of providing safer, more sustainable conditions. Optimum reaction conditions have been identified after high-throughput screening of solvent-reagent combinations, namely the use of Mukaiyama's reagent (Muk) in conjunction with solvent dimethyl carbonate (DMC). The new reaction conditions were also exemplified through the synthesis of a small selection of building-block like molecules and includes the formation of t-butyl esters.

Structure-activity relationship of celecoxib and rofecoxib for the membrane permeabilizing activity

Non-steroidal anti-inflammatory drugs (NSAIDs) achieve their anti-inflammatory effect by inhibiting cyclooxygenase activity. We previously suggested that in addition to cyclooxygenase-inhibition at the gastric mucosa, NSAID-induced gastric mucosal cell death is required for the formation of NSAID-induced gastric lesions in vivo. We showed that celecoxib exhibited the most potent membrane permeabilizing activity among the NSAIDs tested. In contrast, we have found that the NSAID rofecoxib has very weak membrane permeabilizing activity. To understand the membrane permeabilizing activity of coxibs in terms of their structure-activity relationship, we separated the structures of celecoxib and rofecoxib into three parts, synthesized hybrid compounds by substitution of each of the parts, and examined the membrane permeabilizing activities of these hybrids. The results suggest that the sulfonamidophenyl subgroup of celecoxib or the methanesulfonylphenyl subgroup of rofecoxib is important for their potent or weak membrane permeabilizing activity, respectively. These findings provide important information for design and synthesis of new coxibs with lower membrane permeabilizing activity.

Design of fluorine-containing 3,4-diarylfuran-2(5H)-ones as selective COX-1 inhibitors

We report the design and synthesis of fluorine-containing cyclooxygenase-1 (COX-1)-selective inhibitors to serve as prototypes for the development of a COX-1-targeted imaging agent. Deletion of the SO2CH3 group of rofecoxib switches the compound from a COX-2- to a COX-1-selective inhibitor, providing a 3,4-diarylfuran-2(5H)-one scaffold for structure-activity relationship studies of COX-1 inhibition. A wide range of fluorine-containing 3,4-diarylfuran-2(5H)-ones were designed, synthesized, and tested for their ability to selectively inhibit COX-1 in purified protein and human cancer cell assays. Compounds containing a fluoro-substituent on the C-3 phenyl ring and a methoxy-substituent on the C-4 phenyl ring of the 3,4-diarylfuran-2(5H)-one scaffold were the best COX-1-selective agents of those evaluated, exhibiting IC50s in the submicromolar range. These compounds provide the foundation for development of an agent to facilitate radiologic imaging of ovarian cancer expressing elevated levels of COX-1.

Optimizing P,N-bidentate ligands for oxidative gold catalysis: Efficient intermolecular trapping of α-oxo gold carbenes by carboxylic acids

Control confirmed: Optimization of P,N-bidentate ligands (L) reveals the importance of conformation control for intermolecular trapping of reactive α-oxo gold carbene intermediates. As a result, the highly efficient and broadly applicable synthesis of car

Phenacyl esters of acetic acid derivatives and their application for the synthesis of 2-oxo-4-phenyl-5-(phenylhydrazono)-2,5-dihydro-furan-3-derivatives

(Chemical Equation Presented) Coupling of various substituted phenacyl acetates 1 and diazonium salts 3 was studied. If the phenacyl acetates were substituted by an electronaceptor group such as CN or COOEt 3-substituted phenyl-5-(phenyl-hydrazono)-5H-fur

Organic reactions in water: Synthesis of phenacyl esters from phenacyl bromide and potassium salts of aromatic acids in the presence of β-cyclodextrin

A convenient and facile synthesis of phenacyl esters is reported by the reaction of phenacyl bromide with potassium salts of aromatic acids in the presence of β-cyclodextrin in water under neutral conditions. Copyright Taylor & Francis, Inc.

Design and Synthesis of Novel Rofecoxib Analogs as Potential Cyclooxygenase (COX-2) Inhibitors: Replacement of the Methylsulfonyl Pharmacophore by a Sulfonylazide Bioisostere

A group of rofecoxib analogs, having a sulfonylazide (SO2N 3) substituent in place of the methanesulfonyl (SO2CH 3) pharmacophore at the meta-position viz 3-(4-methyl, 4-methoxy, or 4-ethoxyphenyl)-4-(3-sulfonyl

Photolysis of phenacyl esters in a two-phase system

Phenacyl esters are useful photoremovable protecting groups for carboxylic acids in organic synthesis and biochemistry. In this work, simple one-pot arrangements of the phenacyl and 2,5-dimethylphenacyl ester photolysis are proposed. The reactions were performed in both the benzene/water two-phase system and in water. Cetyltrimethylammonium bromide was found to increase substantially the efficiency of the deprotection as well as the purity of the products by lowering the interfacial tension between the phases. Utilizing water as a medium significantly reduced the necessity to use environmentally malign organic solvents. The overall yields varied from 72 to 98% depending on the reaction conditions.

Protecting group release through photoinduced electron transfer: Wavelength control through sensitized irradiation

Phenacyl esters (benzoylmethyl esters, PhCOCH2-OCOR) release carboxylic acids upon photolysis using photosensitizers that are good one-electron donors in the excited state. Herein it is demonstrated that this procedure can be used to control the wavelength of light required to trigger the release. A variety of sensitizers having different absorption profiles are employed and in each case high isolated yields of carboxylic acids are achieved. It is further demonstrated that this method be extended into the visible (>400 nm) region of the spectrum.

Protecting Groups that can be Removed through Photochemical Electron Transfer: Mechanistic and Product Studies on Photosensitized Release of Carboxylates from Phenacyl Esters

Photolysis of electron-donating photosensitizers in the presence of various phenacyl esters (PhCOCH2-OCOR) results in C-O bond scission leading to the formation of acetophenone (PhCOCH3) and the corresponding carboxylic acid (RCO2H). Preparative experiments showed that the carboxylic acids are generated in high or quantitative isolated yields. It is argued that this reaction is initiated by a photoinduced electron transfer from the excited state sensitizer to the phenacyl ester. The latter process forms the anion radical of the phenacyl ester which in turn undergoes rapid C-O bond scission leading to the phenacyl radical and the corresponding carboxylate anion. This mechanism is supported by the following observations. (1) The phenacyl esters quench fluorescence from the sensitizers. (2) Analysis of the redox potentials of the sensitizer excited states and the substrates shows that the proposed electron transfer step is exergonic by 15-20 kcal/mol. (3) The byproducts are indicative of the proposed ion radical intermediates. In particular N-methylaniline is detected when N4Y-dimethylaniline is used as a sensitizer. (4) Competing processes are observed in phenacyl esters whose acid components are themselves labile to single-electron transfer. For example, phenacyl 4-bromophenylacetate showed bromide elimination in competition with deprotection.