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

Chemical Properties

CLEAR LIGHT YELLOW LIQUID

Uses

2,5-Dimethoxytoluene may be used as a reagent in the synthesis of 2,5-dimethoxy-4-methylbenzaldehyde-7-14C. Its IR spectrum has been used to establish the methyl group migration in the acid catalyzed rearrangement of 4-methoxy-4-methylcyclohexadienone.

General Description

2,5-Dimethoxytoluene (1,4-dimethoxy-2-methyl benzene) is a methoxy methyl benzene derivative. It has been synthesized from 2-methylhydroquinone. It is one of the volatile constituents identified from beechwood creosote and Tuber brumale species. It is reported to be one of the thermochemolysis products in Delaware bay particles and dissolved organic matters.

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

Upstream product

• 553-97-9 2-Methyl-1,4-benzoquinone 
• 95-71-6 2-methylbenzene-1,4-diol 
• 74-88-4 methyl iodide 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 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 
• 67-56-1 methanol 
• 27060-75-9 4-bromo-3-methylanisole 
• 124-41-4 sodium methylate 
• 65-85-0 benzoic acid 
• 150-78-7 1,4-dimethoxybezene 

Downstream Products

• 3840-27-5 2,5-dimethoxybenzyl chloride 
• 2675-78-7 2-Chloro-5-methyl-1,4-dimethoxybenzene 
• 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 
• 61042-30-6 (2,5-Dimethoxy-4-methyl-phenyl)-oxo-acetic acid ethyl ester 
• 153906-99-1 (2,4-Dichloro-phenyl)-(2,5-dimethoxy-3-methyl-phenyl)-methanone 
• 153906-98-0 (2-Chloro-phenyl)-(2,5-dimethoxy-3-methyl-phenyl)-methanone 
• 180578-81-8 1,5-Bis-(2,5-dimethoxy-4-methyl-phenyl)-pentane-1,5-dione 
• 180578-80-7 1,6-Bis-(2,5-dimethoxy-4-methyl-phenyl)-hexane-1,6-dione 
• 4925-88-6 2,5-dimethoxy-4-methylbenzaldehyde 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 13720-53-1 2',5'-dimethoxy-4'-methylpropiophenone 

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.

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.

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.