6244-53-7

Usage

Uses

Used in Flavoring and Fragrance Industry:
Ethyl alpha-oxo[1,1'-biphenyl]-4-acetate is used as a flavoring and fragrance agent for its sweet and fruity odor. It is commonly added to perfumes, colognes, and other scented products to provide a fruity or floral note.
Used in Pharmaceutical Industry:
Ethyl alpha-oxo[1,1'-biphenyl]-4-acetate is also used in the manufacture of pharmaceuticals, where it may contribute to the development of new drugs or improve the effectiveness of existing ones.
Used as a Chemical Intermediate in Organic Synthesis:
In addition to its applications in flavoring, fragrance, and pharmaceuticals, ethyl alpha-oxo[1,1'-biphenyl]-4-acetate serves as a chemical intermediate in organic synthesis. This means it is used in the production of other chemical compounds, which can have various applications across different industries.
It is important to handle ethyl alpha-oxo[1,1'-biphenyl]-4-acetate with care, as it may have potential health and environmental hazards if not used properly.

Upstream product

• 5707-44-8 4-ethylbiphenyl 
• 141-78-6 ethyl acetate 
• 64-17-5 ethanol 
• 28179-30-8 1‐([1,1'‐biphenyl]‐4‐yl)‐2,2‐dibromoethan‐1‐one 
• 2999-46-4 Ethyl isocyanoacetate 
• 65690-69-9 N-([1,1'-biphenyl]-4-yl)-4-methylbenzenesulfonamide 
• 14062-23-8 4-biphenylylacetic acid ethyl ester 
• 92-91-1 biphenyl-4-acetaldehyde 
• 140-89-6 potassium ethyl xanthogenate 
• 31603-77-7 4-biphenylacetonitrile 
• 29079-00-3 4-ethynyl-1,1'-biphenyl 
• 3315-91-1 4-biphenylylmagnesium bromide 
• 95-92-1 oxalic acid diethyl ester 
• 92-66-0 4-bromo-1,1'-biphenyl 

Downstream Products

• 6244-54-8 α-hydroxy-α-methylbiphenyl-4-acetic acid 
• 5449-51-4 2-([1,1'-biphenyl]-4-yl)-2-hydroxy-2-phenylacetic acid 
• 5449-21-8 2-([1,1’-biphenyl]-4-yl)-2-oxoacetic acid 
• 73789-98-7 2-([1,1'-biphenyl]-4-yl)-2,2-difluoroacetic acid ethyl ester 
• 1327154-18-6 2-([1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydroquinoxaline 
• 1613439-81-8 N-(3-(N,N-dimethylaminocarbonylphenyl))-2-oxo-2-(4-phenylphenyl)acetamide 
• 1429317-14-5 (R)-tert-butyl 3-(1-(biphenyl-4-yl)-2-ethoxy-1-hydroxy-2-oxoethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 5449-45-6 2-biphenyl-4-yl-hexanoic acid 

Relevant academic research and scientific papers

Copper on charcoal: Cu0nanoparticle catalysed aerobic oxidation of α-diazo esters

By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.

Metal-Free Oxidative Esterification of Ketones and Potassium Xanthates: Selective Synthesis of α-Ketoesters and Esters

A novel and efficient oxidative esterification for the selective synthesis of α-ketoesters and esters has been developed under metal-free conditions. In the protocol, various α-ketoesters and esters are available in high yields from commercially available ketones and potassium xanthates. Mechanistic studies have proven that potassium xanthate not only promotes oxidative esterification but also provides an alkoxy moiety for the reaction, which involves the cleavage and reconstruction of C-O bonds.

Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization

Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording α-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.

Simple preparation method of felbinac

The invention provides a simple preparation method of felbinac. The method comprises the following steps: taking biphenyl and ethyl oxalyl monochloride as initial raw materials; carrying out Friedel-Crafts reaction under the action of aluminum trichloride to generate biphenylethyl glyoxylate under the condition of low temperature; then carrying out alkaline hydrolysis to obtain felbinac salt; carrying out Huang-Minlon reaction reduction and acidification to obtain the felbinac. The method has the advantages of no need of intermediate separation, simplicity and convenience in operation, environment friendliness, high yield and industrial production value.

Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes

A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.

In Situ Generated AgII-Catalyzed Selective Oxo-Esterification of Alkyne with Alcohol to α-Ketoester: Photophysical Study

An expert and easy one-step catalytic method for the multi O-C coupling of alkyne is developed for the synthesis of valuable α-ketoesters and their chiral analogues, in contrast to the generation of esters by a noncatalytic method. The in situ generated powerful AgII catalyst from AgOTf is the workhorse in the oxidative grafting of alkyne with PhIO and alcohol. The radical mechanism is confirmed in our controlled experiments and UV-vis study.

Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters

A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

Destruction and Construction: Application of Dearomatization Strategy in Aromatic Carbon-Nitrogen Bond Functionalization

The formation of carbon-carbon bonds through the functionalization of aromatic carbon-nitrogen bonds is a highly attractive synthetic strategy in the synthesis of aromatic molecules. In this paper, we report a novel aromatic carbon-nitrogen bond functionalization reaction by using a simple dearomatization strategy. Through this process para-substituted anilines serve as a potential aryl source in the construction of a range of functionalized aromatic molecules, such as quaternary carbon centers, α-keto esters, and aldehydes.

Rhodium(iii)-catalyzed C-H allylation of electron-deficient alkenes with allyl acetates

Rhodium-catalyzed C-H allylation of acrylamides with allyl acetates is reported. The use of weakly coordinating directing group resulted in high reaction efficiency, broad functionality tolerance and excellent γ-selectivity, which opens a new synthetic pathway for the access of 1,4-diene skeletons.