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

• 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 
• 32378-21-5 2-(Chloromethyl)-5-methyl-1,4-dimethoxybenzene 
• 3948-92-3 bis(2,5-dimethoxy-4-methylphenyl)methane 
• 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 
• 13736-49-7 2-Hydroxy-5-methoxy-4-methyl-heneicosanophenon 
• 13736-50-0 2-hydroxy-5-heneicosanoyloxy-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.

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.

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.