494-99-5

Basic information

• Product Name: 3,4-Dimethoxytoluene
• Synonyms: 1,2-Dimethoxy-4-methylbenzene;1,2-dimethoxy-4-methyl-Benzene;1,2-Dimethoxy-4-methyl-benzene (4-methylveratrol);4-Methylveratrol;Benzene,1,2-dimethoxy-4-methyl-;Toluene, 3,4-dimethoxy-;4-Methylcatechol dimethyl ether;3,4-DIMETHOXYTOLUENE 99.5%
• CAS NO: 494-99-5
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• EINECS: 207-796-0
• Product Categories: Aromatic Ethers;Anisoles, Alkyloxy Compounds & Phenylacetates
• Mol File: 494-99-5.mol
• Article Data: 63

Chemical Properties

• Melting Point: 22-23 °C(lit.)
• Boiling Point: 133-135 °C50 mm Hg(lit.)
• Flash Point: 185 °F
• Appearance: clear colorless to light yellow liquid
• Density: 1.051 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.171mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: insoluble
• BRN: 2045328
• CAS DataBase Reference: 3,4-Dimethoxytoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dimethoxytoluene(494-99-5)
• EPA Substance Registry System: 3,4-Dimethoxytoluene(494-99-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 494-99-5(Hazardous Substances Data)

Usage

Description

3,4-Dimethoxytoluene, a clear colorless to light yellow liquid, is the main component of essential oil isolated from Phoenix dactylifera L. It is selectively oxidized to the corresponding 1,4-benzoquinones in the presence of hydrogen peroxide/methyltrioxorhenium in 1-butyl-3-methylimidazolium tetrafluoroborate.

Uses

Used in Chromatography:
3,4-Dimethoxytoluene is used as an internal standard in High-Performance Liquid Chromatography (HPLC) quantifications for its stability and reliability in the process.
Used in Essential Oils:
3,4-Dimethoxytoluene is used as a key component in the essential oil extracted from Phoenix dactylifera L., contributing to the oil's properties and applications in various industries.
Used in Chemical Synthesis:
3,4-Dimethoxytoluene is used as a starting material or intermediate in the synthesis of various organic compounds, particularly those involving the formation of 1,4-benzoquinones through selective oxidation processes.

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

Upstream product

• 58-74-2 Papaverine 
• 121-33-5 vanillin 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 93-51-6 2-Methoxy-4-methylphenol 
• 77-78-1 dimethyl sulfate 
• 512-42-5 sodium methyl sulfate 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 
• 74-88-4 methyl iodide 
• 2024-83-1 veratronitrile 
• 186581-53-3 diazomethane 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 53751-40-9 veratryl acetate 
• 22002-45-5 2-bromo-4-methylanisole 
• 124-41-4 sodium methylate 

Downstream Products

• 6575-51-5 4-(4,5-dimethoxy-2-methyl-phenyl)-4-oxo-butyric acid 
• 1164-05-2 bis-(4,5-dimethoxy-2-methyl-phenyl)-methane 
• 7721-62-2 4,5-dimethoxy-2-methylbenzaldehyde 
• 1195-09-1 5-methyl-2-methoxyphenol 
• 7509-11-7 1,2-dimethoxy-4-methyl-5-nitrobenzene 
• 4493-67-8 4,5-dimethoxy-1-methylcyclohexa-1,4-diene 
• 20023-36-3 2,5-dihydro-4-methylanisole 
• 7509-10-6 4,5-dimethoxy-2,3-dinitro-toluene 
• 52806-46-9 1-bromo-4,5-dimethoxy-2-methylbenzene 
• 60987-20-4 4,5-dimethoxy-2-methyl-benzenesulfonyl chloride 
• 116131-35-2 1-Iodo-4,5-dimethoxy-2-methylbenzene 
• 60987-21-5 4,5-dimethoxy-2-methyl-benzenesulfonic acid amide 
• 93-07-2 Veratric acid 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 

Relevant articles and documents

Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups

We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.

Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?

Hydrogenation of over a dozen aromatic compounds, including both heteroarenes and arenes, over palladium on carbon (Pd/C, 1–100 molpercent) with H2-balloon pressure at room temperature is reported. Analyses using pyridine as a model substrate revealed that acetic acid was the best solvent, as using only 1 molpercent Pd/C provided piperidine quantitatively. Substrate scope analysis and density functional theory calculations indicated that reaction rates are highly dependent on frontier molecular orbital characteristics and the steric bulkiness of substituents. Moreover, the established method was used for the concise synthesis of the anti-Alzheimer drug donepezil (Aricept?).