59793-29-2

Usage

Uses

Used in Pharmaceutical Industry:
[1,1'-BIPHENYL]-4-ACETIC ACID METHYL ESTER is used as an intermediate for the synthesis of various pharmaceutical compounds due to its unique chemical properties and reactivity.
Used in Fragrance Industry:
In the fragrance industry, [1,1'-BIPHENYL]-4-ACETIC ACID METHYL ESTER is used as a component in the creation of perfumes and other scented products, capitalizing on its slightly sweet odor.
Used in Organic Synthesis:
[1,1'-BIPHENYL]-4-ACETIC ACID METHYL ESTER is utilized as a key intermediate in organic synthesis, contributing to the production of a range of organic compounds for various applications.

InChI:InChI=1/C15H14O2/c1-17-15(16)11-12-7-9-14(10-8-12)13-5-3-2-4-6-13/h2-10H,11H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 5728-52-9 (4-biphenylyl)acetic acid 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 147283-85-0 (4-Trifluoromethanesulfonyloxy-phenyl)-acetic acid methyl ester 
• 67-56-1 methanol 
• 92-91-1 biphenyl-4-acetaldehyde 
• 74-88-4 methyl iodide 
• 149-73-5 trimethyl orthoformate 
• 616-38-6 carbonic acid dimethyl ester 
• 52449-43-1 (4-chloro-phenyl)-acetic acid methyl ester 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 201230-82-2 carbon monoxide 
• 712-76-5 N-(4-phenyl)benzylamine 

Downstream Products

• 63780-50-7 1,1-biphenyl-4-ylacetamide 
• 5728-52-9 (4-biphenylyl)acetic acid 
• 81770-34-5 2-(4-biphenylyl)-2-methylpropionic acid methyl ester 
• 94209-48-0 5-biphenyl-4-yl-5-ethyl-pyrimidine-2,4,6-trione 
• 77529-41-0 4-(4-biphenylyl)-3-hydroxy-3-pyrroline-2,5-dione 
• 84864-02-8 3-Biphenyl-4-yl-4-methoxy-pyrrole-2,5-dione 
• 84864-01-7 3-Biphenyl-4-yl-4-hydroxy-1-methyl-pyrrole-2,5-dione 
• 61502-90-7 4-Biphenylacetaldehyde 
• 1401354-91-3 C₃₀H₃₁NO₃ 
• 1401355-03-0 C₃₀H₃₁NO₃ 
• 1403365-74-1 (E)-methyl 1-([1,1'-biphenyl]-4-yl)-2-styrylcyclopropanecarboxylate 
• 1403365-77-4 (E)-methyl 1-(naphthalen-2-yl)-2-styrylcyclopropanecarboxylate 
• 1403365-87-6 methyl 1-([1,1'-biphenyl]-4-yl)-2-formylcyclopropanecarboxylate 
• 1403365-97-8 methyl 1-([1,1'-biphenyl]-4-yl)-2-((methylamino)methyl)cyclopropanecarboxylate hydrochloride 

Relevant academic research and scientific papers

Iridium-Catalyzed Amidation of in Situ Prepared Silyl Ketene Acetals to Access α-Amino Esters

Disclosed herein is a convenient Ir-catalyzed amidation of esters to access α-amido esters. Initially prepared silyl ketene acetals are directly employed, without separate purification, for subsequent amidation with an oxycarbonylnitrenoid precursor using the Cp*(LX)Ir(III) catalyst. The α-amidation was facile for both α-aryl and α-alkyl esters. Density functional theory studies revealed that the generation of a putative Ir-nitrenoid is facilitated by the chelation of the countercation additive during the N-O bond cleavage of the nitrene precursor.

Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters

We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.

Preparation method of carboxylic ester compound

The invention relates to a preparation method of a carboxylic ester compound, which comprises the following steps: reacting carboxylic acid with methanol in air under the catalysis of nitrite to obtain an ester compound, the preparation method disclosed by the invention has the advantages of rich raw material sources, cheap and easily available catalyst, mild reaction conditions, simplicity and convenience in operation and the like, a series of fatty carboxylic acids can be modified with high yield, and particularly, the traditional esterification method is generally not suitable for esterification of drug molecules. By utilizing the method, a series of known drug molecules can be modified, so that a shortcut is provided for discovering new drug molecules.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids

A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.

Insertion of Diazo Esters into C-F Bonds toward Diastereoselective One-Carbon Elongation of Benzylic Fluorides: Unprecedented BF3Catalysis with C-F Bond Cleavage and Re-formation

Selective transformation of C-F bonds remains a significant goal in organic chemistry, but C-F insertion of a one-carbon-atom unit has never been established. Herein we report the BF3-catalyzed formal insertion of diazo esters as one-carbon-atom sources into C-F bonds to accomplish one-carbon elongation of benzylic fluorides. A DFT calculation study revealed that the BF3 catalyst could contribute to both C-F bond cleavage and re-formation. This elongation provided α-fluoro-α,β-diaryl esters with a high level of diastereoselectivity. Various benzylic fluorides and diazo esters were applicable. The synthetic utility of this method was demonstrated by the synthesis of a fluoro analogue of a compound that is used as a transient receptor and potential canonical channel inhibitor.

Electrochemical oxidative: Z -selective C(sp2)-H chlorination of acrylamides

An electrochemical method for the oxidative Z-selective C(sp2)-H chlorination of acrylamides has been developed. This catalyst and organic oxidant free method is applicable across various substituted tertiary acrylamides, and provides access to a broad range of synthetically useful Z-β-chloroacrylamides in good yields (22 examples, 73% average yield). The orthogonal derivatization of the products was demonstrated through chemoselective transformations and the electrochemical process was performed on gram scale in flow.

3,3′-Disubstituted Oxindoles Formation via Copper-Catalyzed Arylboration and Arylsilylation of Alkenes

Arylboration and arylsilylation reactions of N-(2-iodoaryl)acrylamides with bis(pinacolato)-diboron (B2pin2) or PhMe2Si-Bpin are developed by using simple CuOAc as the sole catalyst. A range of boron-or silane-bearing 3,3′-disubstituted oxindoles are obtained in moderate to excellent yields. The reaction is proposed to proceed via a domino sequence involving intermolecular olefin borylcupration or silylcupration followed by intramolecular coupling of an alkyl-Cu intermediate with aryl iodide.

Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors

The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alcohol-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.

Palladium-catalyzed intermolecular C-H silylation initiated by aminopalladation

A Pd(ii)-catalyzed intermolecular C-H silylation reaction initiated by aminopalladation has been developed. The C-H bonds were activated by an alkyl Pd(ii) species generated through aminopalladation and then disilylated with hexamethyldisilane to form disilylated indolines as the final products. The reaction provides a new method for the introduction of silyl groups into complex organic molecules.