4142-98-7

Usage

Uses

Used in Chemical Synthesis:
ETHYL 3,5-DIHYDROXYBENZOATE is used as a starting reagent for the synthesis of ethyl 3,5-bis(ω-hydroxyoligo(ethyleneoxy))benzoates. These compounds have potential applications in various fields, such as polymer science and material engineering, due to their unique structural properties.
Used in Coordination Chemistry:
ETHYL 3,5-DIHYDROXYBENZOATE is also used as a starting material in the synthesis of p-alkoxycarbonylated palladium bis(phosphinite) PCP pincer complexes. These complexes are of interest in coordination chemistry and catalysis, as they can exhibit unique reactivity and selectivity in various chemical reactions.

InChI:InChI=1/C9H10O4/c1-2-13-9(12)6-3-7(10)5-8(11)4-6/h3-5,10-11H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 121-48-2 3,5-disulfonicbenzoic acid 
• 105-58-8 Diethyl carbonate 
• 50841-46-8 ethyl 3,5-di(benzyloxy)benzoate 
• 64-67-5 diethyl sulfate 
• 52997-78-1 ethyl 3,5-diacetoxybenzoate 

Downstream Products

• 351002-95-4 3,5-diethoxybenzoic acid ethyl ester 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 117162-88-6 3,5-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzoic acid ethyl ester 
• 148172-12-7 3,5-Bis(dodecyloxy)benzoesaureethylester 
• 84542-51-8 3-hydroxy-5-methoxybenzoic acid ethyl ester 
• 692204-84-5 ethyl 4-iodo-3,5-dihydroxybenzoate 
• 50841-46-8 ethyl 3,5-di(benzyloxy)benzoate 
• 497069-12-2 ethyl 3-(benzyloxy)-5-hydroxybenzoate 
• 859103-39-2 3-hydroxy-5-(4-methoxybenzyloxy)-benzoic acid ethyl ester 
• 897014-05-0 ethyl 3-hydroxy-5-hexyloxybenzoate 
• 918402-90-1 3,5-bis-tert-butoxycarbonyloxy-benzoic acid ethyl ester 
• 959215-82-8 ethyl-3-decyloxy-5-hydroxy-benzoate 
• 945010-96-8 C₃₀H₁₄N₆O₄Cl₄ 
• 945010-81-1 C₃₄H₃₂O₆ 

Relevant academic research and scientific papers

A Cd(ii) and Zn(ii) selective naphthyl based [2]rotaxane acts as an exclusive Zn(ii) sensor upon further functionalization with pyrene

A new multi-functional [2]rotaxane, ROTX, has been synthesized via a Cu(i) catalysed azide-alkyne cycloaddition reaction between Ni(ii) templated azide terminated pseudorotaxane composed of a naphthalene based heteroditopic wheel, NaphMC, and an alkyne terminated stopper. Subsequently, ROTX has been functionalized with pyrene moieties to develop a bifluorophoric [2]rotaxane, PYROTX, having naphthalene and pyrene moieties. Detailed characterization of these two rotaxanes is performed by utilizing several techniques such as ESI-MS, (1D and 2D) NMR, UV/Vis and PL studies. Comparative metal ion sensing studies of NaphMC (a fluorophoric cyclic receptor), ROTX ([2]rotaxane with a naphthyl fluorophore) and PYROTX ([2]rotaxane having naphthyl and pyrene fluorophores) have been performed to determine the effect of dimensionality/functionalization on the metal ion selectivity. Although NaphMC fails to discriminate between metal ions, ROTX serves as a selective sensor for Zn(ii) and Cd(ii). Importantly, PYROTX shows exclusive selectivity towards Zn(ii) over various transition, alkali and alkaline earth metal ions including Cd(ii).

Metal-free C-H functionalization of pyrrolidine to pyrrolinium-based room temperature ionic liquid crystals

The development of ionic liquid crystals (ILCs) using pyrrolidinium cation has received considerable interest due to their higher electrochemical stability. However, high charge density associated with low charge distribution in the fully saturated pyrrol

Optical "blinking" Triggered by Collisions of Single Supramolecular Assemblies of Amphiphilic Molecules with Interfaces of Liquid Crystals

We report that incubation of aqueous dispersions of supramolecular assemblies formed by synthetic alkyl triazole-based amphiphiles against interfaces of thermotropic liquid crystals (LCs; 4-cyano-4′-pentylbiphenyl) triggers spatially localized (micrometer

Rational Design of Supramolecular Dynamic Protein Assemblies by Using a Micelle-Assisted Activity-Based Protein-Labeling Technology

The self-assembly of proteins into higher-order superstructures is ubiquitous in biological systems. Genetic methods comprising both computational and rational design strategies are emerging as powerful methods for the design of synthetic protein complexes with high accuracy and fidelity. Although useful, most of the reported protein complexes lack a dynamic behavior, which may limit their potential applications. On the contrary, protein engineering by using chemical strategies offers excellent possibilities for the design of protein complexes with stimuli-responsive functions and adaptive behavior. However, designs based on chemical strategies are not accurate and therefore, yield polydisperse samples that are difficult to characterize. Here, we describe simple design principles for the construction of protein complexes through a supramolecular chemical strategy. A micelle-assisted activity-based protein-labeling technology has been developed to synthesize libraries of facially amphiphilic synthetic proteins, which self-assemble to form protein complexes through hydrophobic interaction. The proposed methodology is amenable for the synthesis of protein complex libraries with molecular weights and dimensions comparable to naturally occurring protein cages. The designed protein complexes display a rich structural diversity, oligomeric states, sizes, and surface charges that can be engineered through the macromolecular design. The broad utility of this method is demonstrated by the design of most sophisticated stimuli-responsive systems that can be programmed to assemble/disassemble in a reversible/irreversible fashion by using the pH or light as trigger.

Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters

An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented controlling factor for para-selective C-H activation/borylation.

Synthesis of Water-Dispersible Pd Nanoparticles Using a Novel Oxacalixarene Derivative and their Catalytic Application in C–C Coupling Reactions

A novel 5,17-di(hydrazinecarbonyl) tetranitrooxacalix[4]arene (DHOC) derivative has been synthesized and characterized using various spectroscopic techniques. This DHOC derivative has been used to produce water-dispersible catalytically active Pd nanoparticles (PdNps). In the nanoparticle synthesis, DHOC serves as both a reducing and a stabilizing agent, thus simplifying the preparation of the PdNps because no separate reagents are required to reduce and stabilize the nanoparticles. These PdNps were characterized by a number of techniques such as Transmission Electron Microscopy and UV–Visible spectroscopy. The water-dispersible PdNps were 5?±?2?nm in size and showed high catalytic activity in numerous C–C coupling reactions such as the Sonogashira, Suzuki-Miyuara and Heck reactions. Graphical Abstract: [Figure not available: see fulltext.]

Columnar liquid crystalline self-assembly of hydrogen-bonded rod-coil diblock complexes created from pyrazole/benzoic acid derivatives

We synthesized hydrogen-bonded rod-coil diblock complexes having both a rigid rod and a flexible coil by combining bithiophene-conjugated pyrazole derivatives and alkoxy-substituted benzoic acid derivatives. Their self-assembled nanostructures were investigated using polarized optical microscopy, molecular modeling, and X-ray scattering in liquid crystalline (LC) state. They form different types of supramolecularLCphases depending on the numbers and lengths of alkoxy substituents in the benzoic acids. Diblock complexes with low volume ratios of aliphatic coils to rod segments (dioctyloxy chains) self-assembled into lamellar phases; systems with higher ratios (didodecyloxy, trioctyloxy, and tridodecyloxy chains) formed columns. In these columnar structures, two pyrazoles and two benzoic acids formed an aromatic tetramer core through N-H···O and O-H···N hydrogen bonds. Two sets of aromatic tetramers surrounded by flexible aliphatic chains were then stacked to give columnar phases. These are novel examples of supramolecular LC structures comprising hydrogen-bonded pyrazole-benzoic acid derivatives with tetrameric rigid aromatic scaffolds.

Size-regulable vesicles based on anion-π interactions

Taking tetraoxacalix[2]arene[2]triazine as a functionalization platform, a series of new amphiphilic molecules were synthesized in 18 to 53% yields by using a fragment coupling protocol. These amphiphilic molecules self-assembled into stable vesicles in a

Syntheses, structures, and luminescence properties of four metal-organic polymers with undocumented topologies constructed from 3,5-bis((4′- carboxylbenzyl)oxy)benzoate ligand

Solvothermal reactions of one semirigid tricarboxylic acid and transition metal cations in the absence or presence of 1,4-bis(1H-imidazol-4-yl)benzene (1,4-bib) afford four coordination polymers, namely, [Cd(Hbcb)]n (1), and [M(Hbcb)(1,4-bib)]

Rotaxane with multiple functional groups

High-yield syntheses of Cu(II)- and Ni(II)-templated [2]pseudorotaxane precursors (CuPRT and NiPRT, respectively) were achieved by threading bis(azide)bis(amide)-2,2-bipyridine axle into a bis(amide)tris(amine) macrocycle. Single-crystal X-ray structural analysis of CuPRT revealed complete threading of the axle fragment into the wheel cavity, where strong aromatic π-π stacking interactions between two parallel arene moieties of the wheel and the pyridyl unit of axle are operative in addition to metal ion templation. Attachment of a newly developed bulky stopper molecule with a terminal alkyne to CuPRT via a Cu(I)-catalyzed azide-alkyne cycloaddition reaction failed as a result of dethreading of the azide-terminated axle under the reaction conditions. However, the synthesis of a metal-free [2]rotaxane containing triazole with other functionalities in the axle was achieved in ～45% yield upon coupling between azide-terminated NiPRT and the alkyne-terminated stopper. The [2]rotaxane was characterized by mass spectrometry, 1D and 2D NMR (COSY, DOSY, and ROESY) experiments. Comparative solution-state NMR studies of the [2]rotaxane in its unprotonated and protonated states were carried out to locate the position of the wheel on the axle of the metal-free [2]rotaxane. Furthermore, a variable-temperature 1H NMR study in DMSO-d6 of [2]rotaxane supported the kinetic inertness of the interlocked structure, where the newly developed stopper prevents dethreading of the 30-membered wheel from the axle.