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 
• 60-29-7 diethyl ether 
• 578-57-4 2-bromoanisole 
• 917-54-4 methyllithium 
• 529-28-2 4-iodoanisol 
• 40794-04-5 1-chloro-3-methoxy-4-methylbenzene 
• 6609-56-9 2-methoxy-benzonitrile 
• 95-53-4 o-toluidine 
• 34257-57-3 1-(isopropylthio)-2-methoxybenzene 
• 2388-73-0 1-methoxy-2-(methylsulfanyl)benzene 
• 64-19-7 acetic acid 
• 100-66-3 methoxybenzene 
• 369-57-3 benzenediazonium tetrafluoroborate 

Downstream Products

• 33446-14-9 4-(4-methoxy-3-methylphenyl)-4-oxobutyric acid 
• 858007-62-2 4,4'-Dimethoxy-3,3'-dimethyl-benzil 
• 103158-41-4 2-methyl-4-trityl-anisole 
• 861307-00-8 4,4'-dimethoxy-3,3'-dimethyl-thiobenzophenone 
• 32723-67-4 3-methyl-4-anisaldehyde 
• 7288-15-5 3,4-bis-(4-methoxy-3-methyl-phenyl)-hexane 
• 108667-62-5 4-(4-methoxy-3-methyl-phenyl)-valeric acid ethyl ester 
• 106380-49-8 3-bromo-2,2-bis-bromomethyl-1-(4-methoxy-3-methyl-phenyl)-propan-1-one 
• 5394-88-7 1-(4-methoxy-3-methylphenyl)-1-pentanone 
• 859979-73-0 ethyl 2-(4-methoxy-3-methylphenyl)-2-oxoacetate 
• 10024-90-5 4-methoxy-3-methylacetophenone 
• 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 

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

Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols

Chemoselective deoxygenation of carbonyls and alcohols using hydrogen by heterogeneous base-metal catalysts is crucial for the sustainable production of fine chemicals and biofuels. We report an aluminum metal-organic framework (DUT-5) node support cobalt(II) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones, aldehydes, and primary and secondary alcohols, including biomass-derived substrates under 1 bar H2. The single-site cobalt catalyst (DUT-5-CoH) was easily prepared by postsynthetic metalation of the secondary building units (SBUs) of DUT-5 with CoCl2 followed by the reaction of NaEt3BH. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of CoII and AlIII centers in DUT-5-CoH and DUT-5-Co after catalysis. The coordination environment of the cobalt center of DUT-5-Co before and after catalysis was established by extended X-ray fine structure spectroscopy (EXAFS) and density functional theory. The kinetic and computational data suggest reversible carbonyl coordination to cobalt preceding the turnover-limiting step, which involves 1,2-insertion of the coordinated carbonyl into the cobalt-hydride bond. The unique coordination environment of the cobalt ion ligated by oxo-nodes within the porous framework and the rate independency on the pressure of H2 allow the deoxygenation reactions chemoselectively under ambient hydrogen pressure.

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.