4334-88-7

Usage

Uses

Used in Pharmaceutical Industry:
4-Ethoxycarbonylphenylboronic acid is used as a reactant involved in oxidative hydroxylation for the preparation of phenols. This application is crucial in the synthesis of various pharmaceutical compounds, as phenols are key building blocks in the development of drugs with diverse therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-Ethoxycarbonylphenylboronic acid is used as a reactant in homolytic aromatic substitution. This process allows for the introduction of new functional groups onto an aromatic ring, which can be vital for creating novel compounds with specific properties and applications.
Used in Cross-Coupling Reactions:
4-Ethoxycarbonylphenylboronic acid is utilized in cross-coupling reactions with α-bromocarbonyl compounds. These reactions are essential in the formation of carbon-carbon bonds, which are the backbone of many complex organic molecules, including those with potential applications in materials science and pharmaceuticals.
Used in Suzuki-Coupling Reactions:
In the context of Suzuki-coupling reactions, 4-Ethoxycarbonylphenylboronic acid is used as a reactant to form new carbon-carbon bonds with quinoline carboxylates. This reaction is significant in the synthesis of complex organic molecules, particularly those with potential applications in the development of new drugs and pharmaceuticals.
Used in Trifluoromethylation:
4-Ethoxycarbonylphenylboronic acid is also used in trifluoromethylation reactions, where it serves as a reactant to introduce a trifluoromethyl group (CF3) into a molecule. This functional group is known for its unique properties, such as increased lipophilicity and metabolic stability, which can enhance the pharmacokinetic and pharmacodynamic profiles of drug candidates.
Used in Carbometalation of Ynamides:
Lastly, 4-Ethoxycarbonylphenylboronic acid is employed in the carbometalation of ynamides, a reaction that involves the formation of a carbon-metal bond. This process is important in the synthesis of various organic compounds, including those with potential applications in the pharmaceutical and materials science industries.

InChI:InChI=1/C9H11BO4/c1-2-14-9(11)7-3-5-8(6-4-7)10(12)13/h3-6,12-13H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 14047-29-1 4-carboxyphenylboronic acid 
• 106-38-7 para-bromotoluene 
• 13675-18-8 tetrahydroxydiboron 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 13826-24-9 (2,2’-bi(1,3,2-dioxaborolane)) 
• 619-58-9 4-iodobenzoic acid 
• 688-74-4 boric acid tributyl ester 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 5419-55-6 Triisopropyl borate 
• 94-09-7 p-aminoethylbenzoate 
• 5720-05-8 4-methylphenylboronic acid 
• 7664-93-9 sulfuric acid 

Downstream Products

• 288259-77-8 ethyl 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)phenyl]benzoate 
• 47230-38-6 diethyl biphenyl-4,4'-dicarboxylate 
• 19578-70-2 benzyl 2-methylphenyl ether 
• 19247-87-1 5-(4-ethoxycarbonylphenyl)furan-2-carbaldehyde 
• 1032827-76-1 N-(((S)-3-(4-(4-ethoxycarbonylphenyl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 
• 499195-60-7 4-(4-carboethoxyphenyl)-2-chloropyrimidine 
• 1033424-65-5 C₁₈H₂₄O₄ 
• 1169878-16-3 C₂₂H₂₁NO₄ 
• 1169878-14-1 C₁₆H₁₇NO₄ 
• 1193709-08-8 2-[4-(ethoxycarbonyl)phenyl]-1,3,2-dioxaborolane 
• 259541-89-4 4-pyrimidin-2-ylbenzoic acid ethyl ester 
• 1205677-60-6 2-chloro-5-(4-ethylcarboxylatephenyl)-6-methoxy-3-methylpyrazine 
• 1205677-73-1 2,5-bis(4-ethylcarboxylatephenyl)-6-methoxy-3-methylpyrazine 
• 1205677-84-4 2-benzyl-3,6-bis(4-(ethoxycarbonyl)-phenyl)-5-styrylpyrazine 

Relevant academic research and scientific papers

Sensitive thin-layer chromatography detection of boronic acids using alizarin

A new method for the selective and sensitive detection of boronic acids on thin-layer chromatography plates is described. The plate is briefly dipped in an alizarin solution, allowed to dry in ambient air, and observed under 366nm light. Alizarin emits a bright yellow fluorescence only in the presence of a boronic acid.

Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds

Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as negative as approximately - 3 V versus SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.

Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure

The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.

A 4 - carboxyl preparation process of boric acid (by machine translation)

The invention discloses a 4 - carboxyl boric acid process. In order to to iodine benzoic acid as the raw material, by esterification reaction, sediment reaction and hydrolysis reaction to obtain the target product 4 - carboxyl boric acid, the total yield can reach 88.7%. The process route raw materials are cheap and easy to obtain, after-treatment is convenient, high yield, easy industrialized application. (by machine translation)

An Amine Functionalized Metal-Organic Framework as an Effective Catalyst for Conversion of CO2 and Biginelli Reactions

A highly porous and thermally stable anionic Zn(II)-framework, {[(CH3)2NH2+]2[Zn3((μ3-O))(L)2(H2O)]·4DMF·2H2O}n (1), having exposed metal sites and pendant amine groups has been synthesized adopting the solvothermal technique. This anionic 3D framework showed two-fold interpenetration with 45.1% void volume. It has a 3,6-c binodal net with rare sit 3,6-conn topology. The metal bound aqua ligand could be easily removed along with the guest molecules in the lattice upon activation to afford the desolvated framework 1′. This produced exposed metal sites that, along with the pendant amine groups incorporated in the ligand, generated a coordination space in the framework to make it an outstanding heterogeneous catalyst for the chemical fixation of CO2 with various epoxides under atmospheric pressure and in the three-component Biginelli reaction with different aldehydes, ethyl acetoacetate, and urea to afford dihydropyrimidinones.

Metal–Organic Synthetic Transporters (MOST): Efficient Chloride and Antibiotic Transmembrane Transporters

We present the synthesis of two functionalized 2,4,7-triphenylbenzimidazole ligands and demonstrate the formation of their respective metal assemblies in phospholipid membranes. Anion transport experiments demonstrate the formation of metal–organic synthe

Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions

A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.

Synthesis method for carbalkoxy phenylboronic acid

The invention relates to a synthesis method for carbalkoxy phenylboronic acid. Sulfoxide chloride is added into carboxy phenylboronic acid and alkyl alcohol, then a reflux reaction, cooling and filtering and high-temperature vacuum drying are carried out, then water is added, the mixture is stirred and then filtered, and carbalkoxy phenylboronic acid is obtained after room temperature drying. The synthesis method is easy and convenient to operate and high in yield, industrial production is easy to achieve, the market competitiveness of products of this kind is improved.

3,4-dibenzamido benzamide derivative, preparation method and application thereof

The invention discloses a 3,4-dibenzamido benzamide derivative (I), wherein R1, R2 and R3 are respectively and individually hydrogen, fluorine, chlorine, bromine, hydroxyl groups, alkoxy groups, amino groups or substituted amino groups. The alkoxy groups

Versatile Tailoring of Paddle-Wheel ZnII Metal-Organic Frameworks through Single-Crystal-to-Single-Crystal Transformations

A new tetracarboxylate ligand having short and long arms formed 2D layer ZnII coordination polymer 1 with paddle-wheel secondary building units under solvothermal conditions. The framework undergoes solvent-specific single crystal-to-single crystal (SC-SC) transmetalation to produce 1Cu. With a sterically encumbered dipyridyl linker, the same ligand forms non-interpenetrated, 3D, pillared-layer ZnII metal-organic framework (MOF) 2, which takes part in SC-SC linker-exchange reactions to produce three daughter frameworks. The parent MOF 2 shows preferential incorporation of the longest linker in competitive linker-exchange experiments. All the 3D MOFs undergo complete SC-SC transmetalation with CuII, whereby metal exchange in different solvents and monitoring of X-ray structures revealed that bulky solvated metal ions lead to ordering of the shortest linker in the framework, which confirms that the solvated metal ions enter through the pores along the linker axis.