2931-90-0

Basic information

• Product Name: 4-hydroxy-5-methoxyisophthalaldehyde
• Synonyms: 4-Hydroxy-5-methoxy-1,3-benzenedicarbaldehyde;5-Formylvanillin;4-hydroxy-5-methoxy-benzene-1,3-dicarbaldehyde;4-hydroxy-5-methoxybenzene-1,3-dicarbaldehyde
• CAS NO: 2931-90-0
• Molecular Formula: C₉H₈O₄
• Molecular Weight: 180.1574
• EINECS: 220-901-4
• Mol File: 2931-90-0.mol

Chemical Properties

• Melting Point: 119-121 °C
• Boiling Point: 308.2°Cat760mmHg
• Flash Point: 124.8°C
• Appearance: /
• Density: 1.332g/cm³
• Vapor Pressure: 0.000381mmHg at 25°C
• Refractive Index: 1.633
• PKA: 6.00±0.23(Predicted)
• CAS DataBase Reference: 4-hydroxy-5-methoxyisophthalaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-5-methoxyisophthalaldehyde(2931-90-0)
• EPA Substance Registry System: 4-hydroxy-5-methoxyisophthalaldehyde(2931-90-0)

Safety Data

• Hazardous Substances Data: 2931-90-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-hydroxy-5-methoxyisophthalaldehyde is utilized as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its chemical structure allows for the development of new compounds with therapeutic and pesticidal properties, contributing to the advancement of these industries.
Used in Dye and Pigment Production:
As a building block, 4-hydroxy-5-methoxyisophthalaldehyde is employed in the production of dyes and pigments. Its chemical properties enable the creation of a wide range of colors and hues, enhancing the diversity of products available in the market.
Used in Pharmaceutical Research:
4-hydroxy-5-methoxyisophthalaldehyde has been studied for its potential anti-cancer and anti-inflammatory properties. Researchers are interested in exploring its therapeutic potential, which could lead to the development of new drugs for the treatment of various diseases.
Used in Organic Synthesis:
4-hydroxy-5-methoxyisophthalaldehyde is also investigated for its potential use in organic synthesis for the production of various functionalized molecules. Its unique structure allows for the synthesis of a variety of compounds with different applications, further expanding its utility in the chemical industry.

InChI:InChI=1/C9H8O4/c1-13-8-3-6(4-10)2-7(5-11)9(8)12/h2-5,12H,1H3

Upstream product

• 3153-97-7 2-methoxy-4,6-bishydroxymethyl phenol 
• 20240-58-8 3-allyl-4-hydroxy-5-methoxybenzaldehyde 
• 5438-52-8 4-hydroxy-3-methoxy-5-cis-propenyl-benzaldehyde 
• 87743-10-0 3-((dimethylamino)methyl)-4-hydroxy-5-methoxybenzaldehyde 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 2680-81-1 (E)-1-<(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-1-benzofuran-5-yl>-1-propene 
• 98-95-3 nitrobenzene 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 90-05-1 2-methoxy-phenol 
• 7452-10-0 2-hydroxy-3-methoxy-5-methylbenzaldehyde 
• 100-97-0 hexamethylenetetramine 
• 67-66-3 chloroform 
• 121-33-5 vanillin 
• 53175-52-3 2,4-bis-(1,3-diphenyl-imidazolidin-2-yl)-6-methoxy-phenol 

Downstream Products

• 10536-24-0 4,5-dimethoxyisiphthalaldehyde 
• 122472-76-8 4-hydroxy-5-methoxy-isophthalaldehyde-bis-(2-methyl-isonicotinoylhydrazone) 
• 4097-63-6 2-methoxy-4,6-dinitrophenol 
• 2896-66-4 2-methoxy-4,6-dimethylphenol 
• 3934-87-0 5-hydroxyvanillin 
• 2134-91-0 4-hydroxy-5-methoxyisophthalic acid 
• 116315-07-2 1,2-dihydroxy-3,5-diformylbenzene 
• 16534-03-5 4-acetoxy-5-methoxy-isophthalaldehyde 
• 15333-96-7 N-<2-Hydroxy-3-methoxy-5-formyl-benzyliden>-n-propylamin 
• 15333-97-8 N.N'-<5-Methoxy-6-hydroxy-isophthalyliden>-bis- 
• 2785-75-3 3,5-dimethylcatechol 
• 15346-18-6 2-Hydroxy-3-methoxy-5-formyl-benzyliden-acetessigsaeure-aethylester 
• 15334-03-9 N-(2-Hydroxy-3-methoxy-5-formyl-benzyliden)-(2,4-dichlor-anilin) 
• 15334-02-8 N-(2-Hydroxy-3-methoxy-5-formyl-benzyliden)-(p-chlor-anilin) 

Relevant articles and documents

A Dual Colorimetric/Fluorescence System for Determining pH Based on the Nucleophilic Addition Reaction of an o-Hydroxymerocyanine Dye

Owing to their ability to monitor pH in a precise and rapid manner, optical probes have widely been developed for biological and nonbiological applications. The strategies thus far employed to determine pH rely on two types of processes including reversible protonation of amine nitrogen atoms and deprotonation of phenols. We have developed a novel dual, colorimetric/fluorescence system for determining the pH of a solution. This system utilizes an o-hydroxymerocyanine dye that undergoes a nucleophilic addition reaction that subsequently causes reversible structural changes interconverting a merocyanine to a spirocyanine and a spirocyanine to a spiropyran. It was demonstrated that the dye can be employed to measure the pH of solutions in the 2.5-5.75 and 9.6-11.8 ranges with color changes from yellow to dark blue and then to lavender. Moreover, the fluorescence response associated with the spirocyanine-spiropyran transformation of the dye occurring in alkaline solutions provides a precise method. Strike that, reverse it! A novel dual, colorimetric/fluorescence system for determining the pH of a solution has been developed. This system utilizes an o-hydroxymerocyanine dye, which undergoes a nucleophilic addition reaction that subsequently causes reversible structural changes interconverting a merocyanine to a spirocyanine and a spirocyanine to a spiropyran (see scheme).

Trans-A2B-corroles bearing a coumarin moiety - From synthesis to photophysics

Four dyads comprised of cor-role and coumarin units have been synthesised. Three coumarincarboxalde-hydes were synthesized and transformed into the corresponding trans-A2B-corroles by reaction with 5 (pentafluorophenyl)dipyrromethane. It has been proven that this type of direct condensation can lead to the corresponding corroles in moderate yields. The reaction of hydroxybenzaldehydes with vinylphosphonium salts has been identified as the most general method for the preparation of formyl-coumar-ins with various patterns of substitu-ents. The dyad consisting of ketobis-coumarin and corrole was synthesized by Sonogashira coupling. Spectroscopic and photophysical investigations revealed that there is an efficient energy transfer from the coumarin moiety to corrole in all four dyads. Energy transfer can be clearly ascribed to a dipole-dipole mechanism (Foerster) for all dyads that contain luminescent coumarins and to an electron exchange mechanism (Dexter) for the dyad with the non-luminescent one. In the case of the dyad that bears coumarin with a hydroxy group at position 5, an electron-transfer was detected from corrole to coumarin. The latter process is possible because of the suitably low reduction potential of coumarins of this type.

An ICT based ultraselective and sensitive fluorescent probe for detection of HClO in living cells

An ICT based ultraselective and sensitive probe for colorimetric and fluorescent detection of HClO via oxidative cleavage of an alkene linker to epoxide and then to aldehydes was developed through the conjugation of pyridinium with vanilline.

A Multifaceted Hit-Finding Approach Reveals Novel LC3 Family Ligands

Autophagy-related proteins (Atgs) drive the lysosome-mediated degradation pathway, autophagy, to enable the clearance of dysfunctional cellular components and maintain homeostasis. In humans, this process is driven by the mammalian Atg8 (mAtg8) family of proteins comprising the LC3 and GABARAP subfamilies. The mAtg8 proteins play essential roles in the formation and maturation of autophagosomes and the capture of specific cargo through binding to the conserved LC3-interacting region (LIR) sequence within target proteins. Modulation of interactions of mAtg8 with its target proteins via small-molecule ligands would enable further interrogation of their function. Here we describe unbiased fragment and DNA-encoded library (DEL) screening approaches for discovering LC3 small-molecule ligands. Both strategies resulted in compounds that bind to LC3, with the fragment hits favoring a conserved hydrophobic pocket in mATG8 proteins, as detailed by LC3A-fragment complex crystal structures. Our findings demonstrate that the malleable LIR-binding surface can be readily targeted by fragments; however, rational design of additional interactions to drive increased affinity proved challenging. DEL libraries, which combine small, fragment-like building blocks into larger scaffolds, yielded higher-affinity binders and revealed an unexpected potential for reversible, covalent ligands. Moreover, DEL hits identified possible vectors for synthesizing fluorescent probes or bivalent molecules for engineering autophagic degradation of specific targets.

Synthesis of salicylaldehydes from phenols via copper-mediated duff reaction

A copper-mediated Duff reaction for ortho-selective formylation of phenols has been developed. In the presence of copper species, significant improvements of yield and ortho-selectivity of the Duff formylation were achieved, which provides an easy access to salicylaldehydes from phenols.

Novel 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methylbenzofuran derivatives as selective α2C-adrenergic receptor antagonists

The synthesis of a series of 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methyl-2-arylbenzofuran and 4-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)methylbenzofuran-2-carboxamide derivatives as novel α2C-adrenergic receptor antagonists are described. Their affinity at three different human α2-adrenergic receptors is reported, and some of these compounds exhibited high affinity for the α2C-adrenergic receptor with high subtype selectivity. Among them, compound 10e has been found to show the anti-l-dopa-induced dyskinetic activity in marmosets. The structure-activity relationship of these compounds is also discussed.

Characterization of high molecular mass fractions of receiving waters and sediments of a pulp mill by CuO-oxidation and HPLC

High molecular mass fractions were separated by ultrafiltration from water samples collected at four sampling stations downstream and one upstream of a kraft pulp mill. These fractions and three sediment samples containing high molecular mass organic compound were degraded by alkaline cupric oxide oxidation. Lignin and humic compounds in fractions were characterized analyzing their oxidation products by reversed phase HPLC and photodiode array detection. -from Authors

ANODIC ACETOXYLATION OF 2-HYDROXY-3-METHOXY-5-METHYLBENZALDEHYDE AND ITS SCHIFF BASES

Anodic oxidation of 2-hydroxy-3-methoxybenzaldehyde (II) in acetonitrile-acetic acid (3:1) containing sodium acetate gave an acetoxylated product in which the acetoxyl group is attached to the side-chain methyl group.On the other hand, oxidation of Schiff bases (I) derived from II under the same conditions gave cyclohexenetriones.The latter products were shown to be formed by further oxidation of the initially formed acetoxylated Schiff bases, in which the acetoxy group is introduced into the ring meta to the hydroxyl group.Keywords - anodic acetoxylation; cyclic voltametry; controlled potential electrolysis; salicylaldehydes; phenolic Schiff bases; cyclohexenetriones