24599-58-4

Basic information

• Product Name: 2,5-Dimethoxytoluene
• Synonyms: 1,4-dimethoxy-2-methyl-benzen;1,4-Dimethoxy-2-methylbenzene;2-Methylhydroquinone dimethyl ether;Benzene, 1,4-dimethoxy-2-methyl-;Toluene, 2,5-dimethoxy-;2,5-DIMETHOXYTOLUENE;2,5-Dimethoxytoluene, GC 99%;2,5-DIMETHOXYTOLUENE 99%
• CAS NO: 24599-58-4
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• EINECS: 246-343-1
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 24599-58-4.mol
• Article Data: 26

Chemical Properties

• Melting Point: 19-21 °C
• Boiling Point: 218-220 °C751 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: clear slightly yellow liquid
• Density: 1.049 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.152mmHg at 25°C
• Refractive Index: n20/D 1.522(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: PRACTICALLY INSOLUBLE
• CAS DataBase Reference: 2,5-Dimethoxytoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethoxytoluene(24599-58-4)
• EPA Substance Registry System: 2,5-Dimethoxytoluene(24599-58-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 24599-58-4(Hazardous Substances Data)

Usage

Description

2,5-Dimethoxytoluene, also known as 1,4-dimethoxy-2-methyl benzene, is a methoxy methyl benzene derivative that has been synthesized from 2-methylhydroquinone. It is one of the volatile constituents identified from beechwood creosote and Tuber brumale species, and is also reported to be one of the thermochemolysis products in Delaware bay particles and dissolved organic matters. This clear light yellow liquid is characterized by its distinct chemical properties.

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

• 95-71-6 2-methylbenzene-1,4-diol 
• 616-38-6 carbonic acid dimethyl ester 
• 60732-17-4 2,5-dimethoxybenzyl bromide 
• 33524-31-1 2,5-dimethoxybenzyl alcohol 
• 65-85-0 benzoic acid 
• 150-78-7 1,4-dimethoxybezene 
• 67-56-1 methanol 
• 27060-75-9 4-bromo-3-methylanisole 
• 64-17-5 ethanol 
• 13523-12-1 1-bromo-2,5-dimethoxy-3-methylbenzene 
• 39835-11-5 2-hydroxy-4 methoxybenzonitrile 
• 917-58-8 potassium ethoxide 
• 74-88-4 methyl iodide 
• 61176-68-9 Aethyl-2,3,6-tridesoxy-α-L-glycero-hex-2-enopyranosid-4-ulose 

Downstream Products

• 476-43-7 cynodontin 
• 13321-74-9 1-bromo-2,5-dimethoxy-4-methylbenzene 
• 4925-88-6 2,5-dimethoxy-4-methylbenzaldehyde 
• 155126-91-3 2-(2,5-dimethoxy-4-methylbenzoyl)-3,6-dimethoxybenzoic acid 
• 153906-99-1 (2,4-Dichloro-phenyl)-(2,5-dimethoxy-3-methyl-phenyl)-methanone 
• 154659-01-5 2-(2,5-Dimethoxy-4-methyl-benzoyl)-benzoic acid 
• 60732-17-4 2,5-dimethoxybenzyl bromide 
• 60736-94-9 2-Methyl-1,1,4,4-tetramethoxy-2,5-cyclohexadiene 
• 21182-64-9 1-(2,5-dihydroxy-4-methyl-phenyl)-hexadecan-1-one 
• 13720-58-6 1-(2,5-Dimethoxy-4-methyl-phenyl)-ethanone 
• 61042-30-6 (2,5-Dimethoxy-4-methyl-phenyl)-oxo-acetic acid ethyl ester 
• 53581-93-4 1-(2,5-Dimethoxy-4-methyl-phenyl)-butan-3-on 
• 13736-50-0 2-hydroxy-5-heneicosanoyloxy-4-methyl-heneicosanophenon 
• 13736-49-7 2-Hydroxy-5-methoxy-4-methyl-heneicosanophenon 

Relevant articles and documents

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.

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.

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.