21450-56-6

Basic information

• Product Name: 1,2,3,4-TETRAMETHOXYBENZENE
• Synonyms: 1,2,3,4-TETRAMETHOXYBENZENE
• CAS NO: 21450-56-6
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.22
• Mol File: 21450-56-6.mol

Chemical Properties

• Melting Point: 85-88 °C
• Boiling Point: 259.5 °C at 760 mmHg
• Flash Point: 100.9 °C
• Appearance: /
• Density: 1.068 g/cm³
• Vapor Pressure: 0.0209mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: 1,2,3,4-TETRAMETHOXYBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRAMETHOXYBENZENE(21450-56-6)
• EPA Substance Registry System: 1,2,3,4-TETRAMETHOXYBENZENE(21450-56-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 21450-56-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,2,3,4-Tetramethoxybenzene is used as a building block in the synthesis of various organic compounds, leveraging its structure to create a diverse range of chemical products.
Used in Pharmaceutical Development:
1,2,3,4-Tetramethoxybenzene is used as a starting material for the development of new drugs, capitalizing on its medicinal properties to potentially address unmet needs in healthcare.
Used in Antioxidant Applications:
1,2,3,4-Tetramethoxybenzene is studied for its potential antioxidant properties, which could be harnessed to develop products that protect against oxidative stress and related conditions.
Used in Antimicrobial Applications:
1,2,3,4-TETRAMETHOXYBENZENE is also investigated for its antimicrobial properties, suggesting its use in applications that require the inhibition of microbial growth, such as in the development of antimicrobial agents.
Used in Research:
1,2,3,4-Tetramethoxybenzene serves as a subject of research in various scientific fields, including chemistry and medicine, to explore its full potential and unlock new applications.

InChI:InChI=1/C10H14O4/c1-11-7-5-6-8(12-2)10(14-4)9(7)13-3/h5-6H,1-4H3

Upstream product

• 25245-37-8 1-iodo-2,3,4-trimethoxy-benzene 
• 10385-36-1 2,3,4-trimethoxybromobenzene 
• 529-53-3 scutellarein 
• 74-88-4 methyl iodide 
• 52643-52-4 2,3-dimethoxybenzene-1,4-diol 
• 77-78-1 dimethyl sulfate 
• 642-96-6 1,2,3,4-tetrahydroxybenzene 
• 109765-60-8 2,3-dihydroxy-1,4-dimethoxybenzene 
• 124-41-4 sodium methylate 
• 1478593-03-1 C₁₁H₁₃NO₄ 
• 30225-80-0 2,3,4-trimethoxyphenyl acetate 
• 5396-18-9 2'-hydroxy-3',4'-dimethoxyacetophenone 
• 13909-73-4 2',3',4'-trimethoxyacetophenone 
• 87-66-1 2-hydroxyresorcinol 

Downstream Products

• 100142-09-4 1,2-bis-chloromethyl-3,4,5,6-tetramethoxy-benzene 
• 25245-40-3 1-iodo-2,3,4,5-tetramethoxybenzene 
• 489-58-7 melanoxetin 
• 122774-73-6 1,2-dibromo-3,4,5,6-tetramethoxybenzene 
• 30225-96-8 1-(2-hydroxy-3,4,5-trimethoxyphenyl)ethan-1-one 
• 65884-12-0 2,3,4,5-tetramethoxybenzaldehyde 
• 41768-12-1 methylspinazarin 
• 129168-53-2 2-Hydroxy-2',3,4,5,5'-pentamethoxybenzophenon 
• 3117-02-0 2,3-dimethoxy-1,4-benzoquinone 
• 25245-39-0 1-bromo-2,3,4,5-tetramethoxybenzene 
• 109765-60-8 2,3-dihydroxy-1,4-dimethoxybenzene 
• 30225-97-9 1-(2,3,4,5-tetramethoxyphenyl)ethan-1-one 
• 2240-77-9 β-(2,3,4,5-Tetramethoxybenzoyl)propionsaeure 
• 35896-58-3 2,3,4,5-tetramethoxytoluene 

Relevant articles and documents

Synthesis of an Isotopically Labeled Naphthalene Derivative That Supports a Long-Lived Nuclear Singlet State

The synthesis of an octa-alkoxy substituted isotopically labeled naphthalene derivative, shown to have excellent properties in singlet NMR experiments, is described. This highly substituted naphthalene system, which incorporates an adjacent 13C spin pair, is readily accessed from a commercially available 13C2-labeled building block via sequential thermal alkynyl- and arylcyclobutenone rearrangements. The synthetic route incorporates a simple desymmetrization approach leading to a small difference in the chemical shifts of the 13C spin pair, a design constraint crucial for accessing nuclear singlet order. (Chemical Equation Presented).

Polygala tenuifolia-Acori tatarinowii herbal pair as an inspiration for substituted cinnamic α-asaronol esters: Design, synthesis, anticonvulsant activity, and inhibition of lactate dehydrogenase study

Inspired by the traditional Chinese herbal pair of Polygala tenuifolia-Acori Tatarinowii for treating epilepsy, 33 novel substituted cinnamic α-asaronol esters and analogues were designed by Combination of Traditional Chinese Medicine Molecular Chemistry (CTCMMC) strategy, synthesized and tested systematically not only for anticonvulsant activity in three mouse models but also for LDH inhibitory activity. Thereinto, 68–70 and 75 displayed excellent and broad spectra of anticonvulsant activities with modest ability in preventing neuropathic pain, as well as low neurotoxicity. The protective indices of these four compounds compared favorably with stiripentol, lacosamide, carbamazepine and valproic acid. 68–70 exhibited good LDH1 and LDH5 inhibitory activities with noncompetitive inhibition type, and were more potent than stiripentol. Notably, 70, as a representative agent, was also shown as a moderately positive allosteric modulator at human α1β2γ2 GABAA receptors (EC50 46.3 ± 7.3 μM). Thus, 68–70 were promising candidates for developing into anti-epileptic drugs, especially for treatment of refractory epilepsies such as Dravet syndrome.

Practical Synthesis of Polymethylated Flavones: Nobiletin and Its Desmethyl Derivatives

We present a practical synthesis of the polymethoxylated citrus flavone nobiletin that is suitable for use on a hundred gram scale. Ready availability of this compound and its derivatives will aid detailed chemical-biological investigations of their biological activities, including activation of signaling via the cAMP-dependent protein kinase A/extracellular signal-related protein kinase/cAMP response element-binding protein pathway.

Synthesis of isoflavones by tandem demethylation and ring-opening/cyclization of methoxybenzoylbenzofurans

The unexpected conversion of benzoylbenzofurans into isoflavones through an intramolecular cascade that involves deprotection and ring-opening/cyclization is described. This was discovered in an investigation of the possible transformation of benzoylbenzofurans into coumaronochromones. This route affords isoflavones in two major steps from acetophenones and benzoquinones. The transformation was validated by synthesizing differently substituted isoflavone derivatives and further applied to a concise synthesis of a potential anticancer lead compound, glaziovianin A (1).

Studies toward the development of antiproliferative neoclerodanes from salvinorin A

The success rate for central nervous system (CNS) drug candidates in the clinic is relatively low compared to the industry average across other therapeutic areas. Penetration through the blood-brain barrier (BBB) to reach the therapeutic target is a major obstacle in development. The rapid CNS penetration of salvinorin A has suggested that the neoclerodane nucleus offers an excellent scaffold for developing antiproliferative compounds that enter the CNS. The Liebeskind-Srogl reaction was used as the main carbon-carbon bond-forming step toward the synthesis of quinone-containing salvinorin A analogues. Quinone-containing salvinorin A analogues were shown to have antiproliferative activity against the MCF7 breast cancer cell line, but show no significant activity at the κ-opioid receptors. In an in vitro model of BBB penetration, quinone-containing salvinorin A analogues were shown to passively diffuse across the cell monolayer. The analogues, however, are substrates of P-glycoprotein, and thus further modification of the molecules is needed to reduce the affinity for the efflux transporter.

Exploring the reactivity of nickel complexes in hydrodecyanation reactions

In the present study, the nickel-catalyzed hydrodecyanation of organic cyanides with lithium borohydride as a cheap hydride source has been examined in detail. As precatalysts straightforward nickel complexes modified by tridentate O,N,O′-ligands and triphenylphosphane as co-ligand have been applied. Noteworthy, excellent yields and chemoselectivities were feasible for a variety of organic cyanides at low catalyst loadings and low temperature (70 C) within short reaction time (3 h).

PET imaging of nobiletin based on a practical total synthesis

A practical synthesis of nobiletin, a polymethoxylated citrus flavone, was accomplished by utilizing our novel flavone synthesis. Synthetic nobiletin was labelled by selective demethylation and rapid incorporation of 11C atom. Positron emission tomography images successfully visualized the brain distribution, which may provide therapeutic benefits in the treatment of Alzheimer's disease. The Royal Society of Chemistry.

Alternative synthesis of 1,2,3,4-tetramethoxy-5-methylbenzene: A key intermediate for preparing coenzyme Q homologs and analogs

Preparation of 1,2,3,4-tetramethoxy-5-methylbenzene (1) through a new process from pyrogallol is described. In the preparation, a modified mild brominating agent was employed, and a simple introduction of methyl group into aromatic ring through chloromethylation of the corresponding substrate (4), followed by reductive dehalogenation, was achieved successfully with good yields. Copyright Taylor & Francis Group, LLC.

Quinol fatty alcohols as promoters of axonal growth

The synthesis of three series of quinol fatty alcohols (QFAs) and their biological activities on the promotion of axonal growth are described. Interestingly, the 15-(2,5-dimethoxyphenyl)pentadecan-1-ol, the QFA bearing 15 carbon atoms on the side chain (n = 15), shows the most potent promotion of axonal growth in the presence of both permissive and non-permissive naturally occurring substrates such as Sema3A and myelin proteins.

A new fluorogenic transformation: Development of an optical probe for coenzyme Q

(Chemical Equation Presented) A new fluorogenic transformation based on a quinone reduction/lactonization sequence has been developed and evaluated as a tool for probing redox phenomena in a biochemical context. The probe presented herein is an irreversible redox probe and is reduced selectively by biologically relevant quinols such as ubiquinol but is inert to reduced nicotinamides (e.g., NADH). The ensuing cyclization is fast and quantitative and provides a measurable optical response.