24599-58-4

Usage

Uses

Used in Chemical Synthesis:
2,5-Dimethoxytoluene is used as a reagent in the synthesis of 2,5-dimethoxy-4-methylbenzaldehyde-7-14C. Its application in this process is crucial for the production of various chemical compounds and intermediates.
Used in Analytical Chemistry:
The IR (Infrared) spectrum of 2,5-Dimethoxytoluene has been utilized to establish the methyl group migration in the acid-catalyzed rearrangement of 4-methoxy-4-methylcyclohexadienone. This application is significant for understanding the structural changes and reaction mechanisms in organic chemistry.
Used in the Flavor and Fragrance Industry:
As one of the volatile constituents identified from natural sources like beechwood creosote and Tuber brumale species, 2,5-Dimethoxytoluene can be used as a component in the creation of various fragrances and flavors, adding unique scents and enhancing the overall sensory experience of products in this industry.
Used in Environmental Research:
Due to its identification as a thermochemolysis product in Delaware bay particles and dissolved organic matters, 2,5-Dimethoxytoluene can be employed in environmental research to study the chemical composition and behavior of organic matter in aquatic ecosystems, contributing to a better understanding of natural processes and pollution control strategies.

InChI:InChI=1/C9H12O2/c1-7-6-8(10-2)4-5-9(7)11-3/h4-6H,1-3H3

Upstream product

• 67-56-1 methanol 
• 95-71-6 2-methylbenzene-1,4-diol 
• 124-41-4 sodium methylate 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 3840-27-5 2,5-dimethoxybenzyl chloride 
• 67-68-5 dimethyl sulfoxide 
• 61176-68-9 Aethyl-2,3,6-tridesoxy-α-L-glycero-hex-2-enopyranosid-4-ulose 
• 150-78-7 1,4-dimethoxybezene 
• 64-17-5 ethanol 
• 13523-12-1 1-bromo-2,5-dimethoxy-3-methylbenzene 
• 39835-11-5 2-hydroxy-4 methoxybenzonitrile 

Downstream Products

• 856809-86-4 4-(2,5-dimethoxy-4-methyl-phenyl)-4-oxo-butyric acid 
• 3840-27-5 2,5-dimethoxybenzyl chloride 
• 2675-78-7 2-Chloro-5-methyl-1,4-dimethoxybenzene 
• 856181-96-9 1-(2,5-dihydroxy-4-methyl-phenyl)-3-methyl-but-2-en-1-one 
• 476-43-7 cynodontin 
• 13742-19-3 2-methyl-1,4-cyclohexanedione 
• 60732-17-4 2,5-dimethoxybenzyl bromide 
• 32185-64-1 1,4-dimethoxy-2-methyl-5-nitrobenzene 
• 75056-76-7 1-iodo-2,5-dimethoxy-4-methylbenzene 
• 38982-23-9 (2,5-dimethoxy-4-methylphenyl)(phenyl)methanone 
• 53581-93-4 1-(2,5-Dimethoxy-4-methyl-phenyl)-butan-3-on 
• 61042-30-6 (2,5-Dimethoxy-4-methyl-phenyl)-oxo-acetic acid ethyl ester 
• 21182-64-9 1-(2,5-dihydroxy-4-methyl-phenyl)-hexadecan-1-one 
• 60736-94-9 2-Methyl-1,1,4,4-tetramethoxy-2,5-cyclohexadiene 

Relevant academic research and scientific papers

Total synthesis of the fungal metabolite (±)-acremine G: Acceleration of a biomimetic Diels-Alder reaction on silica gel

A total synthesis of the bioactive tetracyclic natural product acremine G has been achieved in which a regio- and stereoselective biomimetic Diels-Alder reaction between two readily assembled building blocks, accelerated on a solid support (silica gel), forms the key step.

Scalable Wolff-Kishner Reductions in Extreme Process Windows Using a Silicon Carbide Flow Reactor

A safe and scalable continuous flow strategy for Wolff-Kishner reductions that employs methanol as the solvent has been developed. The use of low-cost hydrazine as the reducing agent in combination with a caustic base provides an atom-efficient, environmentally friendly method for the deoxygenation of aldehydes and ketones to alkanes. Because of the required harsh and corrosive reaction conditions (200 °C, 50 bar), reactor materials such as stainless steel, glass, or any type of polymer have compatibility problems, rendering this process problematic on a production scale. The use of corrosion-resistant silicon carbide (SiC) as the reactor material opens up the possibility of performing Wolff-Kishner reductions on scale with a considerably improved safety profile. Methanol as the solvent significantly simplifies the workup procedure compared with the generally employed high-boiling solvents such as diethylene glycol. The continuous flow protocol was applied to a number of substrates and provided the desired products in good to high yields with space-time yields of up to 152 g L-1 h-1. In addition, a pharmaceutically valuable active pharmaceutical ingredient precursor was synthesized by employing this higherature/pressure Wolff-Kishner protocol.

Direct Synthesis of Hydroquinones from Quinones through Sequential and Continuous-Flow Hydrogenation-Derivatization Using Heterogeneous Au–Pt Nanoparticles as Catalysts

Pt–Au bimetallic nanoparticle catalysts immobilized on dimethyl polysilane (Pt–Au/(DMPSi-Al2O3)) have been developed for selective hydrogenation of quinones to hydroquinones. High reactivity, selectivity, and robustness of the catalysts were confirmed under continuous-flow conditions. Various direct derivatizations of quinones, such as methylation, acetylation, trifluoromethanesulfonylation, methacrylation, and benzoylation were successfully performed under sequential and continuous-flow conditions to afford the desired products in good to excellent yields. Especially, air-sensitive hydroquinones, such as anthrahydroquinones and naphthohydroquinones, could be successfully generated and derivatized under closed sequential and continuous-flow conditions without decomposition.

Synthesis and antitumor activity evaluation of compounds based on toluquinol

Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties.

Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type Cyclization: Total Synthesis of Akaol A

A Lewis acid catalyzed Nazarov-type cyclization of arylvinylcarbinol has been developed for the asymmetric synthesis of carbotetracyclic core of merosesquiterpenes. The reaction works only in the presence of 2 mol % of Sn(OTf)2 and Bi(OTf)3 in dichloroethane under elevated temperature. The methodology offers the synthesis of a variety of enantioenriched arylvinylcarbinols from commercially available (3aR)-sclareolide 9 in six steps with an eventual concise total synthesis of marine sesquiterpene quinol, akaol A (1a).

Microwave-assisted methylation of dihydroxybenzene derivatives with dimethyl carbonate

Using a focused microwave reactor, methylation with dimethyl carbonate (DMC) of 1,2- and 1,4-dihydroxybenzene derivatives, found in the product spectrum of lignin depolymerisation, leads to the respective aromatic bis-methyl ethers with excellent isolated yields. Stoichiometric as well as catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are effective for the bis-methylation of these dihydroxybenzenes at relatively mild temperatures (160-190 °C). Conversion of resorcinol (1,3-dihydroxybenzene) under similar conditions leads to a mixture of 1,3-dimethoxybenzene and methyl 2,4-dimethoxybenzoate. The unusual reactivity of resorcinol's phenyl ring towards DMC can be explained by the synergic effect of its two strongly activating ortho/para directing groups.

Charge-transfer complex formations of tetracyanoquinone (cyanil) and aromatic electron donors

Single-electron oxidants are the primary reagents for investigations of the new oxidants and the development of electron-accepting materials for application in optoelectronics. Quinones are the well-known class of the neutral single-electron oxidants. Here, we present the properties of the strongest neutral electron acceptor of this class tetracyanoquinone (cyanil) and investigate its electron-accepting strength by analyzing the charge-transfer complex formations with the aromatic donor molecules. Charge-transfer complexes of tetracyanoquinone with aromatic electron donors are characterized spectroscopically in solution and isolated as the single crystals.

Erbium trifluoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation

Erbium trifluoromethanesulfonate is found to be a good catalyst for the Friedel-Crafts acylation of arenes containing electron-donating substituents using aromatic carboxylic acids as the acylating agents under microwave irradiation. An effective, rapid and waste-free method allows the preparation of a wide range of aryl ketones in good yields and in short reaction times with minimum amounts of waste.

ALKYLATION OF PHENOLIC COMPOUNDS

The invention relates to a process for O-alkyiation of a phenolic compound comprising at least two hydroxyl groups bonded to an aromatic hydrocarbon, the process comprising reacting the phenolic compound with an alkylating agent in the presence of a base, at a suitable reaction temperature and for a suitable time period, thereby alkylating the at least two hydroxy] groups. The invention also relates to O-alkylaled phenolic compounds produced by this process.

A highly efficient approach to vanillin starting from 4-cresol

A highly efficient approach to the famous flavor and fragrance compound vanillin has been developed starting from 4-cresol with the attention focused on improving the sustainability of all the reactions. The approach involves a three-step sequence of the quasi-quantitative selective clean oxybromination of 4-cresol, the high-yield selective aerobic oxidation of 2-bromo-4-cresol, and the quantitative methoxylation of 3-bromo-4-hydroxybenzaldehyde with the recovery of pure methanol. Herein, the pivotal oxidation and methoxylation reactions are logically investigated and developed into two concise methodologies. As a green alternative, the approach holds significant value for the sustainable manufacturing of vanillin. the Partner Organisations 2014.