180516-87-4

Usage

Uses

Used in Chemical Biology and Medicinal Chemistry:
4-Carboxylphenylboronic acid pinacol ester is used as a synthetic intermediate for the preparation of various biologically active compounds and pharmaceuticals. Its unique reactivity and stability make it a versatile building block in the synthesis of complex organic molecules.
Used in Molecular Imaging:
4-Carboxylphenylboronic acid pinacol ester is used as a labeling feature in the improvement of transition metal-mediated carbon-carbon as well as carbon-heteroatom cross-coupling reactions. This allows for the preparation of radiolabeled compounds, which are essential for molecular imaging techniques in both research and clinical settings.
Used in Organic Synthesis:
4-Carboxylphenylboronic acid pinacol ester is used as a key component in various organic synthesis reactions, including Suzuki-Miyaura cross-coupling, which is a widely used method for the formation of carbon-carbon bonds. Its presence enhances the efficiency and selectivity of these reactions, leading to the production of desired products with improved yields and purity.

InChI:InChI=1/C13H17BO4/c1-12(2)13(3,4)18-14(17-12)10-7-5-9(6-8-10)11(15)16/h5-8H,1-4H3,(H,15,16)

Upstream product

• 87199-17-5 4-formylphenylboronic acid, 
• 619-58-9 4-iodobenzoic acid 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 7647-01-0 hydrogenchloride 
• 124-38-9 carbon dioxide 
• 195062-61-4 4-chlorophenylboronic acid pinacol ester 
• 586-76-5 4-Bromobenzoic acid 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 494225-46-6 C₁₃H₉BO₄ 
• 73183-34-3 bis(pinacol)diborane 
• 74-11-3 para-chlorobenzoic acid 
• 150-13-0 4-amino-benzoic acid 
• 106-38-7 para-bromotoluene 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 7111-64-0 3′,4′-dichloro-[1,1′-biphenyl]-4-carboxylic acid 
• 5728-32-5 4-(2-methoxyphenyl)benzoic acid 
• 5728-33-6 3'‐methyl‐(1,1'‐biphenyl)‐4‐carboxylic acid 
• 5728-46-1 4′‐cyano‐[1,1′‐biphenyl]‐4‐carboxylic acid 
• 92-89-7 4'-nitro-biphenyl-4-carboxylic acid 
• 5730-78-9 4-(4-aminophenyl)benzoic acid 
• 911370-68-8 4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic acid 
• 331251-53-7 di-(4-tert-octylphenoxy) pentaerythrytil di-[oxycarbonyl-4-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]-benzene] 
• 331251-52-6 tri-(4-tert-octylphenoxy) pentaerythrityl 4-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]-benzoate 
• 380499-68-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid chloride 
• 548776-79-0 3-[(p-nitrophenyl)methoxy]-2,2-dimethyl-1-propanol-[p-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzoate] 
• 1003575-20-9 N-(2-pyrrolidin-1-yl-ethyl)-4-(4,4,5,5-tetramethyl-[1,2,3]dioxaborolan-2-yl)-benzamide 

Relevant academic research and scientific papers

Arrangement of Proteinogenic α-Amino Acids on a Cyclic Peptide Comprising Alternate Biphenyl-Cored ζ-Amino Acids

Aiming at precisely arranging several proteinogenic α-amino acids on a folded scaffold, we have developed a cyclic hexapeptide comprising an alternate sequence of biphenyl-cored ζ-amino acids and proteinogenic α-amino acids such as l-leucine. The amino ac

In Situ Formation of Polymeric Nanoassemblies Using an Efficient Reversible Click Reaction

Polymer–drug conjugates are promising as strategies for drug delivery, because of their high drug loading capacity and low premature release profile. However, the preparation of these conjugates is often tedious. In this paper, we report an efficient meth

4-Carboxyphenylboronic acid-decorated, redox-sensitive rod-shaped nano-micelles fabricated through co-assembling strategy for active targeting and synergistic co-delivery of camptothecin and gemcitabine

To achieve redox-controlled and tumor active targeting synergistic self-delivery of camptothecin and gemcitabine, redox-sensitive rod-shaped nano-micelles are fabricated through co-assembling between camptothecin-disulfide bond-PEG2000-4-carboxyphenylboronic acid and camptothecin-disulfide bond-gemcitabine conjugate. Most of all, for multidrug resistant cancer cell line MCF-7/ADR which is more resistant against CPT, increasing content of CPT in the formulation is favorable for synergistic effect of CPT and GEM drug combination. Benefiting from simple co-assembling strategy, it is easy and convenient to adjust drug ratio of CPT/GEM to optimize the synergism of drug combination. In addition, nano-micelles fabricated from co-assembling are endowed with both high absolute drug concentration and enhanced colloidal stability, which is helpful to in vivo studies. Transmission electron microscopy observation confirmed the rod-shaped morphology, which is beneficial to cellular internalization, of co-assembled nano-micelles resulting from π-π stacking interactions of CPT moieties and appropriate hydrophilic and hydrophobic interactions during co-assembling. Taking advantages of the specific interactions between 4-carboxyphenylboronic acid and sialic acid, co-assembled nano-micelles exerted enhanced cellular internalization. Noteworthy, compared with cocktail mixture of free CPT and GEM, nano-micelles greatly alleviated drug reflux against MCF-7/ADR and 4T1 cells. The nano-micelles realized redox-controlled ratio-metric and synchronous delivery of CPT and GEM, thereby pronounced in vitro synergistic antiproliferative effect against MCF-7/ADR and 4T1cells. Furthermore, in vivo bio-distribution analysis indicated the preferential accumulation of nano-micelles at tumor site, which could increase therapeutic efficacy and decrease side effects of non-selective anticancer drugs. Taken together, the redox-sensitive CPBA decorated co-assembled nano-micelles provided a promising strategy for tumor active targeting and redox-controlled intracellular synergistic combinational delivery of chemotherapeutics.

Traceless Staudinger Ligation to Introduce Chemical Diversity on β-Lactamase Inhibitors of Second Generation

We explored the traceless Staudinger ligation for the functionalization of the C2 position of second generation β-lactamase inhibitors based on a diazabicyclooctane (DBO) scaffold. Our strategy is based on the synthesis of phosphine phenol esters and thei

A synthetic route to 1-(4-boronobenzyl)-1H-pyrrole

The synthesis of 1-(4-boronobenzyl)-1H-pyrrole was investigated using three different routes. Two key routes that involved the introduction of the boronate group protected as the pinacol ester, failed, due to deprotection problems. The route involving the

Sequential Connection of Mutually Exclusive Catalytic Reactions by a Method Controlling the Presence of an MOF Catalyst: One-Pot Oxidation of Alcohols to Carboxylic Acids

A functionalized metal-organic framework (MOF) catalyst applied to the sequential one-pot oxidation of alcohols to carboxylic acids controls the presence of a heterogeneous catalyst. The conversion of alcohols to aldehydes was acquired through aerobic oxidation using a well-known amino-oxy radical-functionalized MOF. In the same flask, a simple filtration of the radical MOF with mild heating of the solution completely altered the reaction media, providing radical scavenger-free conditions suitable for the autoxidation of the aldehydes formed in the first step to carboxylic acids. The mutually exclusive radical-catalyzed aerobic oxidation (the first step with MOF) and radical-inhibited autoxidation (the second step without MOF) are sequentially achieved in a one-pot manner. Overall, we demonstrate a powerful and efficient method for the sequential oxidation of alcohols to carboxylic acids by employing a readily functionalizable heterogeneous MOF. In addition, our MOF in-and-out method can be utilized in an environmentally friendly way for the oxidation of alcohols to carboxylic acids of industrial and economic value with broad functional group tolerance, including 2,5-furandicarboxylic acid and 1,4-benzenedicarboxylic acid, with good yield and reusability. Furthermore, MOF-TEMPO, as an antioxidative stabilizer, prevents the undesired oxidation of aldehydes, and the perfect "recoverability"of such a reactive MOF requires a re-evaluation of the advantages of MOFs from heterogeneity in catalytic and related applications.

Green synthesis method of aromatic acid

The invention discloses a green synthesis method of aromatic acid. Nickel-catalyzed carbonyl insertion is carried out on aryl iodine in the presence of formate, acid anhydride, a phosphine ligand andan organic solvent by using a nickel catalyst to obtain the aromatic acid. Efficient catalytic conversion is realized by utilizing the cheap nickel catalyst, the reaction conditions are mild, and theoperation is simple.

Nickel-catalyzed carboxylation of aryl iodides with lithium formate through catalytic CO recycling

A protocol for the Ni-catalyzed carboxylation of aryl iodides with formate has been developed with good functional group compatibility for the synthesis of a variety of aromatic carboxylic acids under mild conditions. The reaction tolerates other functionalities for cross-coupling, such as aryl bromide, aryl chloride, aryl tosylate, and aryl pinacol boronate. The reaction proceeds through a carbonylation process with in situ generated carbon monoxide in the presence of a catalytic amount of acetic anhydride and lithium formate, avoiding the use of gaseous CO. The strategy of CO recycling in catalytic amounts is critical for the success of the reaction.

Cobalt-catalyzed carboxylation of aryl and vinyl chlorides with CO2

The transition-metal-catalyzed carboxylation of aryl and vinyl chlorides with CO2 is rarely studied, and has been achieved only with a Ni catalyst or combination of palladium and photoredox. In this work, the cobalt-catalyzed carboxylation of aryl and vinyl chlorides and bromides with CO2 has been developed. These transformations proceed under mild conditions and exhibit a broad substrate scope, affording the corresponding carboxylic acids in good to high yields.

Development of Potent PfCLK3 Inhibitors Based on TCMDC-135051 as a New Class of Antimalarials

The protein kinase PfCLK3 plays a critical role in the regulation of malarial parasite RNA splicing and is essential for the survival of blood stage Plasmodium falciparum. We recently validated PfCLK3 as a drug target in malaria that offers prophylactic,