7310-95-4

Usage

Uses

Used in Chemical Synthesis:
2-Hydroxy-5-methylisophthalaldehyde is used as a key reagent for the synthesis of various organic compounds, including 2-(2′-vinyloxyethoxy)-5-methylisophthaldehyde and chiral calixsalen macrocycles. It plays a crucial role in the formation of these complex molecules due to its unique chemical structure.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-hydroxy-5-methylisophthalaldehyde is used as a starting material for the synthesis of several pharmaceutical compounds, such as 3-[(2,4-Dichlorophenyl)iminomethyl]-2-hydroxy-5-methylbenzaldehyde, a Schiff base, and 2-hydroxy-3-dimethoxymethyl-5-methylbenzaldehyde. These compounds have potential applications in the development of new drugs and therapeutic agents.
Used in Material Science:
2-Hydroxy-5-methylisophthalaldehyde is also utilized in the synthesis of macrobicyclic ligands (MSB) and acyclic Schiff-base ligands, which are essential components in the development of advanced materials with specific properties, such as catalysts, sensors, and molecular machines.
Used in Polymer Industry:
In the polymer industry, 2-hydroxy-5-methylisophthalaldehyde is used as a monomer in the production of polymers with specific properties, such as 4-methyl-2,6-divinylphenol. These polymers can be employed in various applications, including coatings, adhesives, and composite materials.
Overall, 2-hydroxy-5-methylisophthalaldehyde is a versatile compound with applications in various industries, including chemical synthesis, pharmaceuticals, material science, and polymer production. Its unique chemical structure and properties make it an essential component in the development of new compounds and materials with potential applications in various fields.

InChI:InChI=1/C9H8O3/c1-6-2-7(4-10)9(12)8(3-6)5-11/h2-5,12H,1H3

Upstream product

• 91-04-3 2,6-bis(hydroxymethyl)-4-methylphenol 
• 127-68-4 sodium 3-nitrobenzenesulfonate 
• 153904-93-9 1,3-bis-hydroxymethyl-5-methyl-2-(toluene-4-sulfonyloxy)-benzene 
• 65448-72-8 2-hydroxy-3-(hydroxymethyl)-5-methylbenzaldehyde 
• 76107-45-4 5-methyl-2-tosyl-isophthalaldehyde 
• 19497-26-8 tributylammonium 
• 20023-36-3 2,5-dihydro-4-methylanisole 
• 68-12-2 N,N-dimethyl-formamide 
• 71128-83-1 2-methoxy-5-methyl-1,3-benzenedicarboxaldehyde 
• 181042-20-6 O-(2,6-diformyl-4-methylphenyl) dimethylthiocarbamate 
• 6327-85-1 2,6-bis(hydroxymethyl)-4-methyl-anisole 
• 106-44-5 p-cresol 
• 76-05-1 trifluoroacetic acid 
• 100-97-0 hexamethylenetetramine 

Downstream Products

• 102262-03-3 2,6-bis-(N-2-pyridylformidoyl)-4-methylphenol 
• 73940-71-3 2-Hydroxy-5-methyl-3-{[(E)-2-pyridin-2-yl-ethylimino]-methyl}-benzaldehyde 
• 222532-55-0 2-formyl-4-methyl-6-((p-methoxyphenylimino)methyl)phenol 
• 191790-72-4 2,6-bis((4-methoxyphenylimino)methyl)-4-methylphenol 
• 96594-20-6 2,6-bis(N-[(2-dimethylamino)ethyl]iminomethyl)-4-methylphenol 

Relevant academic research and scientific papers

Dinucleating Ligand Platforms Supporting Indium and Zinc Catalysts for Cyclic Ester Polymerization

The synthesis of the first alkoxide-bridged indium complex supported by a chiral dinucleating ligand platform (1), along with its zinc analogue (2), is reported. Both complexes are synthesized in a one-pot reaction starting from a chiral dinucleating bis(diamino)phenolate ligand platform, sodium ethoxide, and respective metal salts. The dinucleating indium analogue (7) based on an achiral ligand backbone is also reported. Indium complexes bearing either the chiral or achiral ligand catalyze the ring-opening polymerization of racemic lactide (rac-LA) to afford highly heterotactic poly(lactic acid) (PLA; Pr > 0.85). The indium complex bearing an achiral ligand affords essentially atactic PLA from meso-LA. The role of the dinucleating ligand structure in catalyst synthesis and polymerization activity is discussed.

Water oxidation catalyzed by molecular di- and nonanuclear Fe complexes: Importance of a proper ligand framework

The synthesis of two molecular iron complexes, a dinuclear iron(iii,iii) complex and a nonanuclear iron complex, based on the dinucleating ligand 2,2′-(2-hydroxy-5-methyl-1,3-phenylene)bis(1H-benzo[d]imidazole-4-carboxylic acid) is described. The two iron complexes were found to drive the oxidation of water by the one-electron oxidant [Ru(bpy)3]3+.

A carbonothioate-based highly selective fluorescent probe with a large Stokes shift for detection of Hg2+

Mercury (Hg) is one of the heavy metal pollutants in the environment. Even a very small amount of mercury can cause serious harm to human beings. Herein, we reported a new carbonothioate-based fluorescent probe for the detection of Hg2+ without interference from other metal ions. This probe possessed a very large Stokes shift (192?nm), which could improve the detection sensitivity by minimizing the interferences resulted from self-absorption or auto-fluorescence. With the addition of Hg2+ to the probe solution, considerable fluorescence enhancement was observed. Additionally, the Hg2+ concentration of 0–16?μM and fluorescence intensity showed a good linear relationship (y?=?22106×?+?53108, R2?=?0.9955). Finally, the proposed probe was used to detect Hg2+ in real water samples, and its result was satisfactory. Therefore, our proposed probe would provide a promising method for the determination of Hg2+ in the environment.

Remarkable ESIPT induced NIR emission by a selective colorimetric dibenzimidazolo diimine sensor for acetate

A new dibenzimidazolo diimine sensor (DDS) has been designed and synthesized for selective detection of acetate ion. Significant naked eye recognized color change of DDS solution from light yellow to pink upon addition of only acetate ion is accompanied with near infra red (NIR) emission exploiting excited state intramolecular proton transfer (ESIPT).

A water-soluble metal–organic coordination polymer of Zn(II) Schiff base complex in interaction with DNA: diagnosing the mode of binding by in vitro studies

In this paper, in vitro DNA binding of a water-soluble metal–organic coordination polymer of Zn(II) Schiff base complex was considered. By focusing on the cooperative effect of multi-Zn(II) centers of the complex, the affinity and mode of binding were investigated by some techniques, e.g., absorption and fluorescence spectroscopy, circular dichroism spectroscopy, viscosity measurement, molecular docking, iodide quenching studies and effect of ionic strength on the complex–DNA binding. The calculated value of Kb = 1.3 × 103?M?1 represented a good affinity of the Zn(II) complex to DNA. From the experimental methods and docking studies, non-classical intercalation (i.e., van der Waals interactions, groove binding or external binding) was proposed as the main mode of binding.

A detailed study on the interaction of a novel water-soluble glycine bridged zinc(II) Schiff base coordination polymer with BSA: Synthesis, crystal structure, molecular docking and cytotoxicity effect against A549, Jurkat and Raji cell lines

A novel water-soluble glycine bridged zinc(II) Schiff base coordination polymer was synthesized by the condensation of 2,6-diformyl-4-methylphenol, glycine, and zinc(II) chloride. The complex was characterized by 1HNMR, FT-IR, elemental analyses and X-ray crystallography. The polymeric complex was built up of two glycine-bridged Zn/L moieties, where L denotes the Schiff base containing 2,6-diformyl-4-methylphenol and glycine in 1:1?M ratio. The carboxylic group of L was coordinated to the Zn atoms of the neighboring moieties; thus each Zn center was five-coordinated. The interaction between polymeric Zn(II) complex and bovine serum albumin (BSA) was studied by UV–Vis, fluorescence, and synchronous fluorescence spectroscopic techniques. By considering the sign and values of the thermodynamic parameters (ΔH and ΔS), it is clear that the binding between BSA and complex was exothermic and entropy-driven and electrostatic interactions between the complex and BSA was supposed. Site-selective binding studies revealed that the complex were mainly located in the region of site II (subdomain IIIA) in BSA. From the synchronous fluorescence spectroscopic studies, it is concluded that complex could bind to tyrosine and tryptophan residues simultaneously. The Kb values indicated a high binding affinity of the complex to BSA. In vitro anticancer activity of the polymeric Zn(II) complex was evaluated against A549, Jurkat, and Raji cell lines by MTT assay. The complex was remarkably active against the cell lines and can be a good candidate for an anticancer therapy. Theoretical docking studies were performed to further investigate the BSA binding interactions.

A NIR-emitting cyanine with large Stokes shifts for live cell imaging: Large impact of the phenol group on emission

There are a limited number of near-infrared (NIR) emitting (λem = 700-900 nm) molecular probes for imaging applications. A NIR-emitting probe that exhibits emission at ～800 nm with a large Stokes shift was synthesized and found to exhibit excellent selectivity towards mitochondria for live-cell imaging. The photophysical properties were attributed to an excited cyanine structure via intramolecular charge transfer (ICT) involving a phenol group.

Investigation of the complex structure, comparative DNA-binding and DNA cleavage of two water-soluble mono-nuclear lanthanum(III) complexes and cytotoxic activity of chitosan-coated magnetic nanoparticles as drug delivery for the complexes

Two water-soluble mono-nuclear macrocyclic lanthanum(III) complexes of 2,6-diformyl-4-methylphenol with 1,3-diamino-2-propanol (C1) or 1,3-propylenediamine (C2) were synthesized and characterized by UV–Vis, FT-IR, 13C and 1H NMR spectroscopy and elemental analysis. C1 complex was structurally characterized by single-crystal X-ray diffraction, which revealed that the complex was mononuclear and ten-coordinated. The coordination sites around lanthanum(III) were occupied with a five-dentate ligand, two bidentate nitrates, and one water molecule. The interaction of complexes with DNA was studied in buffered aqueous solution at pH 7.4. UV–Vis absorption spectroscopy, emission spectroscopy, circular dichroism (CD) and viscometric measurements provided clear evidence of the intercalation mechanism of binding. The obtained intrinsic binding constants (Kb) 9.3 × 103 and 1.2 × 103 M? 1 for C1 and C2, respectively confirmed that C1 is better intercalator than C2. The DNA docking studies suggested that the complexes bind with DNA in a groove binding mode with the binding affinity of C1 > C2. Moreover, agarose gel electrophoresis study of the DNA-complex for both compounds revealed that the C1 intercalation cause ethidium bromide replacement in a competitive manner which confirms the suggested mechanism of binding. Finally, the anticancer experiments for the treated cancerous cell lines with both synthesized compounds show that these hydrophilic molecules need a suitable carrier to pass through the hydrophobic nature of cell membrane efficiently.

Lanthanide cryptate monometallic coordination complexes

We report the synthesis, characterisation and magnetic properties of six novel neutral lanthanide cryptate coordination complexes. Reaction of 2,6-diformyl-4-methylphenol, tris(2-aminoethyl)amine and Ln(OTf)3·9H2O in the ratio 3?:?2?:?1, respectively, and in the presence of base affords the isolation of the six complexes LnL·4H2O (Ln = Tb (1), Dy (2), Ho (3), Er (4), Tm (5) and Yb (6)), with H3L being the cryptand N[(CH2)2NCH-R-CHN-(CH2)2]3N (R = m-C6H2OH-2-Me-5). Powder X-ray diffraction confirms that the six complexes are isostructural. The crystal structure of 6 reveals that the Ln(iii) centre is heptacoordinated, in a geometry close to a monocapped distorted octahedron and lies on a pseudo (non-crystallographically imposed) C3 axis. This coordination sphere is similar to the one found in the previously studied Ln(trensal) complexes (H3trensal = 2,2′,2′′-tris(salicylideneimino)triethylamine). The static and dynamic magnetic properties of these complexes were investigated by SQUID magnetometry. Crystal field parameters were determined for all complexes by modelling of the direct current magnetic susceptibility and variable-temperature-variable-field magnetisation data. As for Ln(trensal), only complexes containing the Kramers ions Dy, Er and Yb displayed out-of-phase susceptibility signals in SQUID measurements in an applied magnetic field. Investigation of the dynamic susceptibility of the Yb complex revealed that the magnetic relaxation is governed by a direct process at low temperatures and a Raman process at higher temperatures, similar to Yb(trensal). This journal is

Transition metal complexes of 2, 6-di ((phenazonyl-4-imino) methyl)-4-methylphenol: Structure and biological evaluation

A symmetric ligand 2, 6-di ((phenazonyl-4-imino)methyl)-4-methylphenol (Dpmp) and its cobalt dinuclear complex (Co2(Dpmp) 2(NO3)2(H2O)2·NO3· EtOH, (1) and zinc mononuclear complex Zn(Dpmp)(NO3)2, (2) have been prepared. The crystal structures were determined by single-crystal X-ray diffraction. The biological activity has been evaluated by examining their anti-oxidative activity and ability to bind to bovine serum albumin (BSA) and calf-thymus DNA (CT DNA) with UV-vis absorption, fluorescence, viscosity measurements and circular dichroism (CD) spectroscopies. The complexes exhibit good binding propensity to BSA and CT DNA. Both 1 and 2 have been found to promote cleavage of pUC19 DNA in the absence of any reducing agent. Antioxidant tests in vitro show the compounds possess significant antioxidant activity against superoxide and hydroxyl radicals.