578-58-5

Basic information

• Product Name: 2-Methylanisole
• Synonyms: 1-methoxy-2-methyl-benzen;2-Methylanisol;2-Methylmethoxybenzene;Anisole, o-methyl-;Methyl o-cresyl ether;Methyl o-methylphenyl ether;o-Cresyl methyl ether;o-Methoxytoluene
• CAS NO: 578-58-5
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.16
• EINECS: 209-426-3
• Product Categories: Anisoles, Alkyloxy Compounds & Phenylacetates;Ethers;Organic Building Blocks;Oxygen Compounds;Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 578-58-5.mol
• Article Data: 103

Chemical Properties

• Melting Point: -34.1°C
• Boiling Point: 170-172 °C(lit.)
• Flash Point: 125 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.985 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.65mmHg at 25°C
• Refractive Index: n20/D 1.516(lit.)
• Storage Temp.: Flammables area
• Water Solubility: immiscible
• BRN: 1857415
• CAS DataBase Reference: 2-Methylanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylanisole(578-58-5)
• EPA Substance Registry System: 2-Methylanisole(578-58-5)

Safety Data

• Hazard Codes: F
• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 578-58-5(Hazardous Substances Data)

Usage

Description

2-Methylanisole, also known as o-cresol methyl ether, is a monomethoxybenzene that is derived from o-cresol, where the phenolic hydroxy group has been converted to the corresponding methyl ether. It is a clear colorless to light yellow liquid, soluble in alcohol and ether, but insoluble in water. 2-Methylanisole is found in mastic oils, virgin olive oils, and frankincense, and it possesses a pungent, warm, floral odor with earthy, walnut undertones and a sweet, fruity, nut-like flavor at low levels.

Uses

Used in Chemical Synthesis:
2-Methylanisole is used as an intermediate in the chemical synthesis of various compounds, particularly those with a methylhydroquinone core. It plays a crucial role in the total synthesis of complex organic molecules, such as (±)-heliannuol D, its epimer, and the phenolic sesquiterpene mutisianthol.
Used in Flavor and Fragrance Industry:
2-Methylanisole is used as a flavoring agent due to its sweet, fruity, nut-like flavor at low levels. It is also used in the fragrance industry for its naphthyl, camphoreous, phenolic, and woody aroma with a salicylate nuance.
Used in Solvent Applications:
2-Methylanisole serves as a polar aprotic solvent in various chemical reactions and processes, making it a valuable component in the chemical and pharmaceutical industries.
Used in the Food Industry:
As a 'green' solvent with a boiling point of 171°C, 2-Methylanisole is utilized in the food industry as a flavor ingredient, adding unique taste characteristics to various products.
Occurrence:
2-Methylanisole is naturally found in starfruit, mastic gum oil, and rooibus tea (Aspalathus linearis), contributing to their distinct flavors and aromas.

Preparation

2-Methylanisole is synthesized by methylation of o-cresol using dimethylsulfate in caustic soda at 40°C.synthesis of 2-methylanisole: Make sodium hydroxide into a 20% solution, stir and mix with o-cresol, cool to below 10°C, and slowly add dimethyl sulfate dropwise. After the addition was completed, the temperature was raised to 40 °C for 20 min, and then reacted with 100 °C for 12 h. Then the reactant was washed with water until neutral, water was removed, distilled, and the fraction at 171°C was collected to obtain the finished product of 2-methylanisole.

Flammability and Explosibility

Flammable

InChI:InChI=1/3C8H10O/c1-7-3-5-8(9-2)6-4-7;1-7-4-3-5-8(6-7)9-2;1-7-5-3-4-6-8(7)9-2/h3*3-6H,1-2H3

Upstream product

• 67-56-1 methanol 
• 4549-72-8 sodium o-cresolate 
• 6609-56-9 2-methoxy-benzonitrile 
• 95-48-7 ortho-cresol 
• 80-48-8 methyl p-toluene sulfonate 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 95-53-4 o-toluidine 
• 95-49-8 2-methylchlorobenzene 
• 865-33-8 potassium methanolate 
• 34257-57-3 1-(isopropylthio)-2-methoxybenzene 
• 2388-74-1 1-methoxy-3-methylsulfanyl-benzene 
• 64-19-7 acetic acid 
• 100-66-3 methoxybenzene 

Downstream Products

• 103158-41-4 2-methyl-4-trityl-anisole 
• 32723-67-4 3-methyl-4-anisaldehyde 
• 93-25-4 2-methoxyphenylacetic acid 
• 26507-91-5 2-methoxy-3-methylbenzoic acid 
• 108667-62-5 4-(4-methoxy-3-methyl-phenyl)-valeric acid ethyl ester 
• 5394-88-7 1-(4-methoxy-3-methylphenyl)-1-pentanone 
• 859979-73-0 ethyl 2-(4-methoxy-3-methylphenyl)-2-oxoacetate 
• 2954-63-4 1-(4-methoxy-3-methylphenyl)-2-methyl-1-propanone 
• 99070-16-3 2-bromo-1-(4-methoxy-3-methylphenyl)ethanone 
• 107777-42-4 5-benzenesulfonyl-2-methoxy-toluene 
• 31040-84-3 4-tert-butyl-2-methylanisole 
• 60736-71-2 3-methyl-4-methoxybenzyl chloride 
• 18102-31-3 2-methoxy-3-methylphenol 
• 2207-57-0 2-methoxy-3-methyl-1,4-benzoquinone 

Relevant articles and documents

Solvolysis of o-methylbenzenediazonium tetrafluoroborate in acidic methanol-water mixtures. Further evidence for nucleophilic attack on a solvent separated aryl cation

Rate constants for dediazoniation product formation and arenediazonium ion loss and product yields of solvolysis of o-methylbenzenediazonium tetrafluoroborate in acidic methanol-water mixtures at T = 35 °C are reported. Observed rate constants for diazonium ion loss and product formation are the same, increasing about 45% ongoing from water to methanol, and are not affected by added electrolytes like HCl, NaCl, and CuCl2. Only three dediazoniation products are detected, o-cresol, o-chlorotoluene, and o-anisole. All data are consistent with a rate-determining step formation of an aryl cation that reacts immediately with available nucleophiles. The selectivity of the reaction toward nucleophiles, S, which can be is low and essentially constant upon changing solvent composition, suggesting that the nucleophilic attack takes place on a solvent separated aryl cation.

Impact of oxygen vacancies in Ni supported mixed oxide catalysts on anisole hydrodeoxygenation

The hydrodeoxygenation (HDO) activity of anisole has been investigated over Ni catalysts on mixed metal oxide supports containing Nb–Zr and Ti–Zr in 1:1 and 1:4 ratios. XRD patterns indicate the incorporation of Ti (or Nb) into the ZrO2 framewo

Optimizing the carburization conditions of supported rhenium carbide for guaiacol conversion

The present work evaluates the effect of ethylene content of a carburization mixture on the formation of carburized rhenium supported on activated carbon. The resulting catalysts were characterized by N2 physisorption, X-ray diffraction, Raman spectroscopy, X-ray photoelectron spectroscopy and temperature-programmed reduction, and the results show a strong effect on the final phase obtained. A high amount of ethylene inhibited the carburization process, resulting in carbon formation, while a lower amount (≤ 35 %) of ethylene was favorable to the formation of the carbide phase. The catalysts were evaluated for the hydrodeoxygenation (HDO) of guaiacol, a bio-oil model compound, and a high yield of benzene (50 %), a desirable aromatic compound, was obtained at complete conversion over the catalysts containing the carbide phase.

Ceramic boron carbonitrides for unlocking organic halides with visible light

Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C-H, C-C, and C-S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C-X (carbon-halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. This journal is