4376-27-6

Basic information

• Product Name: 2-(biphenyl-4-yl)-2-oxoethyl acetate
• Synonyms: 2-(Biphenyl-4-yl)-2-oxoethyl acetate; 2-[1,1'-Biphenyl]-4-yl-2-oxoethyl acetate; Acetic acid, 2-oxo-2-(1,1'-biphenyl-4-yl)ethyl ester; ethanone, 2-(acetyloxy)-1-[1,1'-biphenyl]-4-yl-
• CAS NO: 4376-27-6
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.2806
• Mol File: 4376-27-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 395.9°C at 760 mmHg
• Flash Point: 175.5°C
• Density: 1.141g/cm³
• Vapor Pressure: 1.77E-06mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: 2-(biphenyl-4-yl)-2-oxoethyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(biphenyl-4-yl)-2-oxoethyl acetate(4376-27-6)
• EPA Substance Registry System: 2-(biphenyl-4-yl)-2-oxoethyl acetate(4376-27-6)

Safety Data

• Hazardous Substances Data: 4376-27-6(Hazardous Substances Data)

Usage

General Description

2-(biphenyl-4-yl)-2-oxoethyl acetate is a chemical compound with the molecular formula C17H14O3. It is a derivative of acetate and contains a biphenyl structure with an attached acetoxy group. 2-(biphenyl-4-yl)-2-oxoethyl acetate is commonly used as a flavoring agent in the food industry and as a fragrance in the cosmetics and perfume industries. It is also utilized in the synthesis of pharmaceuticals and as a building block in organic chemistry. It is important to handle this compound carefully and according to safety guidelines, as it may pose health risks if not properly handled or used in excessive quantities.

Upstream product

• 61668-23-3 2-diazo-1-biphenyl-4-yl-ethanone 
• 64-19-7 acetic acid 
• 135-73-9 2-Bromo-4'-phenylacetophenone 
• 127-08-2 potassium acetate 
• 127-09-3 sodium acetate 
• 56956-34-4 Hepta-2,4-diynyl-trimethyl-ammonium; iodide 
• 75-36-5 acetyl chloride 
• 92-91-1 biphenyl-4-acetaldehyde 
• 108-24-7 acetic anhydride 
• 3218-36-8 4-Phenylbenzaldehyde 
• 92-52-4 biphenyl 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 218903-49-2 N-(1-([1,1'-biphenyl]-4-yl)vinyl)acetamide 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Downstream Products

• 7496-43-7 [1,1'-biphenyl]-4-yl(4-([1,1'-biphenyl]-4-yl)-1H-imidazol-2-yl)methanone 

Relevant articles and documents

MACROLIDE BIOSYNTHESIS-II ORIGIN OF THE CARBON SKELETON AND OXYGEN ATOMS OF THE ERYTHROMYCINS

Feeding of propionate to cultures of Streptomyces erythreus gave erythromycin A and B labeled at C-1, 3, 5, 7, 9, 11 and 13, as established by (13)C NMR analysis of the derived 2'-benzoate esters.Incorporation of propionate labled C-2, 4, 6, 8, 10, 12, and 20 while feeding of ethylsuccinate, an in vivo precursor of methylmalonate, gave rise to seven pairs of enhanced and coupled doublets in the spectra of labeled erythromycin A and B benzoate.Subsequent incorporation of propionate and (13)C NMR analysis established the presence of excess (18)O at C-1, 3, 5, 9, 11, and 13 in both erythromycins A and B, as evidenced by the corresponding isotopically shifted (13)C(18)O peaks.These results establish that in the biosynthesis of erythromycin all the O atoms of the initial aglycone, 6-deoxyerythronolide B (3) originate directly from propionate.

PhI(OAc)2-promoted umpolung acetoxylation of enamides for the synthesis of α-acetoxy ketones

Umpolung is a fundamental concept in organic chemistry, which provides an alternative strategy for the synthesis of target compounds which were not easily accessible by conventional methods. Herein, a mild and efficient PhI(OAc)2-promoted umpolung acetoxylation reactions of enamides was developed for the synthesis of α-acetoxy ketones. The reaction tolerates a wide range of functional groups and affords α-acetoxy ketones in good to excellent yields. PhI(OAc)2 serves as a source of acetoxy in the reaction.

Silver acetate mediated acetoxylations of alkyl halides

Silver acetate promotes the acetoxylation of alkyl halides under neutral reaction conditions. The reaction is applicable to primary and activated secondary alkyl halides, and 2,2-dibromoacetophenones for preparing the corresponding acetates in good yields. The presence of ester, amide, nitrile, hydroxy, and OTBDMS functions on the substrate is tolerated.

Synthesis and biological evaluation of quinoline salicylic acids as P-selectin antagonists

Leukocyte recruitment of sites of inflammation and tissue injury involves leukocyte rolling along the endothelial wall, followed by firm adherence of the leukocyte, and finally transmigration of the leukocyte across cell junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewisx (sLex) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis. High-throughput screening of the Wyeth chemical library identified the quinoline salicylic acid class of compounds (1) as antagonists of P-selectin, with potency in in vitro and cell-based assays far superior to that of sLex. Through iterative medicinal chemistry, we identified analogues with improved P-selectin activity, decreased inhibition of dihydrooratate dehydrogenase, and acceptable CYP profiles. Lead compound 36 was efficacious in the rat AIA model of rheumatoid arthritis.