3-Methylanisole

Base Information

• Chemical Name: 3-Methylanisole
• CAS No.: 100-84-5
• Molecular Formula: C8H10O
• Molecular Weight: 122.167
• Hs Code.: 2929-09
• European Community (EC) Number: 202-893-4
• NSC Number: 6255
• UNII: UI9I3Y6WTZ
• DSSTox Substance ID: DTXSID2051500
• Nikkaji Number: J4.985I
• Pharos Ligand ID: 35C6J5UT3K7H
• Metabolomics Workbench ID: 111215
• ChEMBL ID: CHEMBL349791
• Mol file: 100-84-5.mol

Synonyms:3-methoxytoluene

Chemical Property of 3-Methylanisole

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 1.8mmHg at 25°C
• Melting Point: -47oC
• Refractive Index: n20/D 1.513(lit.)
• Boiling Point: 172.2 °C at 760 mmHg
• Flash Point: 54.4 °C
• PSA: 9.23000
• Density: 0.941 g/cm³
• LogP: 2.00360
• Storage Temp.: Flammables area
• Water Solubility.: Soluble in alcohol and insoluble in water.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 122.073164938
• Heavy Atom Count: 9
• Complexity: 80.6

Purity/Quality:

99% ^*data from raw suppliers

3-Methoxytoluene >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-22
• Safety Statements: 16-23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: CC1=CC(=CC=C1)OC
• General Description: 3-Methylanisole (also known as m-methylanisole) is an arene compound that participates in Friedel-Crafts acylation reactions, where its nucleophilicity and reaction conditions influence the formation of unexpected products. The study highlights that higher molar proportions of 3-methylanisole and elevated temperatures can facilitate novel polyaryl compound synthesis, with the reaction pathway being affected by complexation involving AlCl3 and dichloroacetylchloride. This demonstrates its utility as a substrate in synthetic organic chemistry for generating structurally diverse derivatives.

Technology Process of 3-Methylanisole

There total 90 articles about 3-Methylanisole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(2R,3S)-2,3-dihydroxy-1-methylcyclohexa-4,6-diene (41977-20-2) + methyl iodide (74-88-4) → 2-methylmethoxybenzene (578-58-5) + (5S,6R)-dimethoxy-1-methylcyclohexa-1,3-diene + 1-methoxy-3-methyl-benzene (100-84-5)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 0 ℃; for 1.5h;

DOI:10.1016/0022-328X(89)87278-X

Reference yield: 42.0%

vanillin triflate (194018-68-3) → 3-methoxybenzyl alcohol (6971-51-3) + 1-methoxy-3-methyl-benzene (100-84-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 40h; under 760.051 Torr;

DOI:10.1021/acs.oprd.6b00314

Reference yield: 19.0%

methanol (67-56-1) + phenol (108-95-2,27073-41-2) → p-methylanizole (104-93-8) + 2-methylmethoxybenzene (578-58-5) + 2-methoxy-1,3-dimethylbenzene (1004-66-6) + 2,4-dimethylanisole (6738-23-4) + methoxybenzene (100-66-3) + 1-methoxy-3-methyl-benzene (100-84-5)

Guidance literature:

APTi-II-770; at 349.9 ℃; Product distribution; alkylation; other catalysts, other temperatures; also cresols, further products;

upstream raw materials:

3-methoxyphenyl bromide

diethyl ether

2-bromo-3-methylanisole

lithium dimethylamide

Downstream raw materials:

4-oxo-4-(4-methoxy-2-methyl-phenyl)-trans-crotonic acid

4-(4-methoxy-2-methylphenyl)-4-oxo-but-1-oic acid

4-(4-hydroxy-2-methyl-phenyl)-4-oxo-butyric acid

5-(4-methoxy-2-methyl-phenyl)-5-oxo-valeric acid

Refernces

NOVEL FRIEDEL-CRAFTS REACTIONS OF SOME ARENES

10.1016/S0040-4020(01)90320-5

The research focuses on novel secondary Friedel-Crafts acylation reactions of certain arenes, including dimethyl resorcinol, m-xylene, m-methylanisole, and m-chlorotoluene, using dichloroacetylchloride and anhydrous AlCl3 as catalysts. The purpose of the study was to explore the formation of unexpected products, which was found to depend on the nucleophilicity of the arene and the electrophilicity of the acyl carbonyl of the initially formed acylated product. The research concluded that higher molar proportions of the arene and sometimes elevated temperatures are necessary for the generation of these products, and the reaction pathway is influenced by the formation of possible complexes of AlCl3 and dichloroacetylchloride with groups adjacent to the dichloroacetyl function, especially at higher temperatures. The study demonstrated the potential of this method for preparing novel polyaryl compounds using substrates of varied nucleophilicity at different reaction temperatures.