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

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

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 
• 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 
• 614-13-1 2-methoxy-5-methyl-1,4-benzoquinone 

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.

Methylation with Dimethyl Carbonate/Dimethyl Sulfide Mixtures: An Integrated Process without Addition of Acid/Base and Formation of Residual Salts

Dimethyl sulfide, a major byproduct of the Kraft pulping process, was used as an inexpensive and sustainable catalyst/co-reagent (methyl donor) for various methylations with dimethyl carbonate (as both reagent and solvent), which afforded excellent yields of O-methylated phenols and benzoic acids, and mono-C-methylated arylacetonitriles. Furthermore, these products could be isolated using a remarkably straightforward workup and purification procedure, realized by dimethyl sulfide‘s neutral and distillable nature and the absence of residual salts. The likely mechanisms of these methylations were elucidated using experimental and theoretical methods, which revealed that the key step involves the generation of a highly reactive trimethylsulfonium methylcarbonate intermediate. The phenol methylation process represents a rare example of a Williamson-type reaction that occurs without the addition of a Br?nsted base.

Molybdenum-Catalyzed Deoxygenation Coupling of Lignin-Derived Alcohols for Functionalized Bibenzyl Chemicals

With the growing demand for sustainability and reducing CO2 footprint, lignocellulosic biomass has attracted much attention as a renewable, carbon-neutral and low-cost feedstock for the production of chemicals and fuels. To realize efficient utilization of biomass resource, it is essential to selectively alter the high degree of oxygen functionality of biomass-derivates. Herein, we introduced a novel procedure to transform renewable lignin-derived alcohols to various functionalized bibenzyl chemicals. This strategy relied on a short deoxygenation coupling pathway with economical molybdenum catalyst. A well-designed H-donor experiment was performed to investigate the mechanism of this Mo-catalyzed process. It was proven that benzyl carbon-radical was the most possible intermediate to form the bibenzyl products. It was also discovered that the para methoxy and phenolic hydroxyl groups could stabilize the corresponding radical intermediates and then facilitate to selectively obtain bibenzyl products. Our research provides a promising application to produce functionalized aromatics from biomass-derived materials.

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?).

Cleavage of CC and Co bonds in β-O-4 linkage of lignin model compound by cyclopentadienone group 8 and 9 metal complexes

Degradation of 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphe-noxy)propane-1,3-diol (1), a model compound for lignin β-O-4 linkage was examined with iron, ruthenium, rhodium and iridium complexes bearing cyclopentadienone ligand. Cyclopentadienone iron complex gave only a small amount of degraded product with reduced molecular weight. Cyclopentadienone ruthenium complex, so called Shvo's catalyst, afforded 3,4-dimethoxybenzaldehyde (a3) in 14.3% yield after CαCβ bond cleavage. On the other hand, cyclopentadienone group-9 metal complexes catalyzed CβO bond cleavage to afford guaiacol (b1) as a main product in up to 74.9% yield.

Decyanation method of nitrile organic compound

The invention provides a decyanation method of a nitrile organic compound. The nitrile organic compound shown in a general formula (1), a sodium reagent, crown ether and a proton donor are subjected to decyanation reaction in an organic solvent I to generate an organic compound shown in a general formula (2). According to the method, a Na/15-crown-5/H2O system is adopted, so that nitrile organic matters can be converted into a decyanation product, and the generation of amine byproducts is inhibited. The new method does not need to use liquid ammonia as a solvent, and is safer and more convenient to operate. The required sodium dispersoid is low in price; and the 15-crown-5 can be recycled and repeatedly used. The method has the advantages of good chemical selectivity, wide substrate application range, good functional group compatibility and the like.

Reductive Cleavage of Unactivated Carbon-Cyano Bonds under Ammonia-Free Birch Conditions

A general protocol for the reductive cleavage of unactivated carbon-cyano bonds in aliphatic nitriles has been achieved under single-electron-transfer conditions using Na/15-crown-5/H2O. Electron is supplied by the electride derived from bench-stable sodium dispersions and recoverable 15-crown-5. H2O provides the proton source and suppresses the reduction of aromatic moieties. Compared with the Na/NH3 electride system generated under traditional Birch conditions, this ammonia-free electride system is more practical and features better reactivity and chemoselectivity for the decyanations of a broad range of aliphatic nitriles.

Selective, Catalytic, and Metal-Free Coupling of Electron-Rich Phenols and Anilides Using Molecular Oxygen as Terminal Oxidant

Selective oxidative homo- and cross-coupling of electron-rich phenols and anilides was developed using nitrosonium tetrafluoroborate as a catalyst. Oxidative coupling of phenols revealed unusual selectivities, which translated into the unprecedented synthesis of inverse Pummerer-type ketones. Mechanistic studies suggest that oxidative coupling of phenols and anilides shares a common pathway via homolytical heteroatom-hydrogen bond cleavage. Nitrosonium salt catalysis was applied for cross-dehydrogenative coupling initiated by generation of heteroatom-centered radicals.

Two Stereoinduction Events in One C?H Activation Step: A Route towards Terphenyl Ligands with Two Atropisomeric Axes

Herein we disclose the synthesis of original chiral scaffolds—ortho-orientated terphenyls presenting two atropisomeric Ar–Ar axes. These unusual structures were built up by using the C?H activation approach, and remarkably, both chiral axes were controlled with excellent stereoselectivity in a single transformation. During the reaction, not only does atroposelective functionalization of a biaryl precursor occur to establish one stereogenic axis, but an unprecedented atropo-stereoselective C?H arylation also takes place to generate the second stereogenic element. These enantiomerically pure ortho-terphenyls show an original tridimensional structure and thus constitute a unique foundation for building up a library of enantiomerically pure bidentate ligands, such as the new ligands S/N-Biax and diphosphine BiaxPhos.

Manganese-Catalyzed Direct Deoxygenation of Primary Alcohols

Deoxygenation of alcohols is an important tool in the repertoire of defunctionalization methods in modern synthetic chemistry. We report the base-metal-catalyzed direct deoxygenation of benzylic and aliphatic primary alcohols via oxidative dehydrogenation/Wolff-Kishner reduction. The reaction is catalyzed by a well-defined PNP pincer complex of Earth-abundant manganese, evolving H2, N2, and water as the only byproducts.