21004-11-5

Basic information

• Product Name: 2,5-Dimethoxy-1,4-benzenedicarboxylic acid
• Synonyms: 2,5-Dimethoxy-1,4-benzenedicarboxylic acid
• CAS NO: 21004-11-5
• Molecular Formula: C₁₀H₁₀O₆
• Molecular Weight: 226.18
• Mol File: 21004-11-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 265 °C
• Boiling Point: 434.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.391±0.06 g/cm3(Predicted)
• PKA: 3.26±0.10(Predicted)
• CAS DataBase Reference: 2,5-Dimethoxy-1,4-benzenedicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethoxy-1,4-benzenedicarboxylic acid(21004-11-5)
• EPA Substance Registry System: 2,5-Dimethoxy-1,4-benzenedicarboxylic acid(21004-11-5)

Safety Data

• Hazardous Substances Data: 21004-11-5(Hazardous Substances Data)

Usage

General Description

2,5-Dimethoxy-1,4-benzenedicarboxylic acid, also known as veratric acid, is a naturally occurring organic compound found in a variety of plants. It is classified as a benzoic acid derivative and is commonly used as a precursor in the synthesis of other organic compounds. Veratric acid has antioxidant properties and has been studied for its potential therapeutic uses, such as anti-inflammatory and antimicrobial activities. It is also a key intermediate in the biosynthesis of lignin, a complex organic polymer found in plant cell walls. Veratric acid has also been investigated for its potential role in the treatment of certain health conditions, including neurodegenerative diseases and cancer.

Upstream product

• 32176-94-6 4-methyl-2,5-dimethoxy-benzoic acid 
• 51829-43-7 1,4-dihydroxymethyl-2,5-dimethoxybenzaldehyde 
• 173267-23-7 diethyl-2,5-dimethoxy-1,4-benzenedicarboxylate 
• 100964-58-7 2,5-bis(ethoxymethyl)-1,4-dimethoxybenzene 
• 7310-97-6 2,5-dimethoxyterephthalaldehyde 
• 610-92-4 2,5-dihydroxy-1,4-benzenedicarboxylic acid 
• 77-78-1 dimethyl sulfate 
• 4655-68-9 2,5-Dimethoxy-1,4-benzoldicarbonitril 
• 13949-81-0 2,5-bis(hydroxymethylene)benzene-1,4-diol 
• 123-31-9 hydroquinone 
• 3209-15-2 4-methyl-2,5-dihydroxybenzoic acid 
• 50-85-1 2-hydroxy-p-toluic acid 
• 28221-89-8 2,6-dimethyl benzo(1,2-b;4,5-b)difuran 
• 1951-36-6 2,5-dihydroxyterephthaldeyde 

Downstream Products

• 21004-12-6 2,5-dimethoxyterephthalic acid dimethyl ester 
• 56486-55-6 2,5-dimethoxyterephthaloyl dichloride 
• 443643-12-7 1,4-bis(5'-(pyridin-2-yl)-1'H-1',2',4'-triazol-3'-yl)-2,5-dimethoxybenzene 
• 443643-19-4 1,4-bis(acylpyridin-2'-ylamidrazone)-2,5-dimethoxybenzene 
• 1198616-69-1 C₈₈H₁₄₂N₁₂O₁₈ 
• 1263320-86-0 C₁₁₂H₁₇₈N₄O₁₂ 
• 1263320-80-4 C₈₄H₁₂₂N₄O₁₂ 
• 1263320-93-9 C₁₂₈H₂₁₀N₄O₁₂ 
• 1312291-64-7 poly[(μ4-2,5-dimethoxybenzene-1,4-dicarboxylato)manganese(II)] 
• 1312291-65-8 poly[(μ4-2,5-dimethoxybenzene-1,4-dicarboxylato)zinc(II)] 
• 1541182-86-8 C₆₄H₆₀N₁₂O₁₆ 

Relevant articles and documents

Fine-tuning the pore structure of metal-organic frameworks by linker substitution for enhanced hydrogen storage and gas separation

The modification of metal-organic frameworks (MOFs) by functionalizing ligands has been investigated for improved properties. In this study, by introducing substituents to the backbone of organic linkers, isostructural dihydroxy-/dialkoxy-functionalized Zr-MOFs were delicately constructed and sophisticatedly characterized for crystallinity, morphology, porosity and structural defects. Pure-component CO2, CH4, N2, and H2adsorption isotherms on the microporous synthesized materials were investigated under the pressure up to 10 MPa at 303 K. By the ideal adsorbed solution theory (IAST) model, enhanced adsorption selectivity towards CO2/N2, CO2/CH4, CH4/N2and CO2/H2binary mixtures was observed compared to the parent material, and dihydroxy functionalization endows the material with high selectivity towards CO2/H2. Moreover, the diethoxy-functionalized material with narrow cavities exhibits improved high pressure H2adsorption due to structural defects and strong overlapping potentials.

Experimental, Structural, and Computational Investigation of Mixed Metal-Organic Frameworks from Regioisomeric Ligands for Porosity Control

Porosity control and structural analysis of metal-organic frameworks (MOFs) can be achieved using regioisomeric ligand mixtures. While ortho-dimethoxy-functionalized MOFs yielded highly porous structures and para-dimethoxy-functionalized MOFs displayed almost nonporous properties in their N2 isotherms after evacuation, regioisomeric ligand-mixed MOFs showed variable N2 uptake amount and surface area depending on the ligand-mixing ratio. The quantity of N2 absorbed was tuned between 20 and 300 cm3/g by adjusting the ligand-mixing ratio. Both experimental analysis and computational modeling were performed to understand the porosity differences between ortho- A nd para-dimethoxy-functionalized MOFs. Detailed structural analysis using X-ray crystallographic data revealed significant differences in the coordination environments of DMOF-[2,3-(OMe)2] and DMOF-[2,5-(OMe)2] (DMOF = dabco MOF, dabco = 1,4-diazabicyclo[2.2.0]octane). The coordination bond between Zn2+ and carboxylate in the ortho-functionalized DMOF-[2,3-(OMe)2] was more rigid than that in the para-functionalized DMOF-[2,5-(OMe)2]. Quantum-chemical simulation also showed differences in the coordination environments of Zn secondary building unit surrounded by methoxy-functionalized ligands and pillar ligands. In addition, the binding energy differences between Zn2+ and regioisomeric ligands (ortho- A nd para-dimethoxy-functionalized benzene-1,4-dicarboxylates) explained the rigidity and porosity changes of the mixed MOFs upon evacuation and perfectly matched with experimental N2 adsorption and X-ray crystallography data.

Increasing Alkyl Chain Length in a Series of Layered Metal-Organic Frameworks Aids Ultrasonic Exfoliation to Form Nanosheets

Metal-organic framework nanosheets (MONs) are attracting increasing attention as a diverse class of two-dimensional materials derived from metal-organic frameworks (MOFs). The principles behind the design of layered MOFs that can readily be exfoliated to form nanosheets, however, remain poorly understood. Here we systematically investigate an isoreticular series of layered MOFs functionalized with alkoxy substituents in order to understand the effect of substituent alkyl chain length on the structure and properties of the resulting nanosheets. A series of 2,5-alkoxybenzene-1,4-dicarboxylate ligands (O2CC6H2(OR)2CO2, R = methyl-pentyl, 1-5, respectively) was used to synthesize copper paddle-wheel MOFs. Rietveld and Pawley fitting of powder diffraction patterns for compounds Cu(3-5)(DMF) showed they adopt an isoreticular series with two-dimensional connectivity in which the interlayer distance increases from 8.68 ? (R = propyl) to 10.03 ? (R = pentyl). Adsorption of CO2 by the MOFs was found to increase from 27.2 to 40.2 cm3 g-1 with increasing chain length, which we attribute to the increasing accessible volume associated with increasing unit-cell volume. Ultrasound was used to exfoliate the layered MOFs to form MONs, with shorter alkyl chains resulting in higher concentrations of exfoliated material in suspension. The average height of MONs was investigated by AFM and found to decrease from 35 ± 26 to 20 ± 12 nm with increasing chain length, with the thinnest MONs observed being only 5 nm, corresponding to five framework layers. These results indicate that careful choice of ligand functionalities can be used to tune nanosheet structure and properties, enabling optimization for a variety of applications.