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
• Uses: 3-Methylanisole, is widely used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photo initiators and agrochemicals. It is also used as a solvent and in perfumery. 3-Methylanisole was used to study the functionalized core of calyciphylline A-type alkaloids.

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%

(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%

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%

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

• 1、 Geise, C. Michael,Hadad, Christopher M.,Zheng, Fengmei,Shevlin, Philip B.. "An experimental and computational evaluation of the energetics of the isomeric methoxyphenylcarbenes generated in carbon atom reactions". . p. 355 - 364. Retrieved 2002.
• 2、 Jones. "-". . p. 197,203. Retrieved 1968.
• 3、 Huang, Jian-Lin,Dai, Xi-Jie,Li, Chao-Jun. "Iridium-catalyzed direct dehydroxylation of alcohols". . p. 6496 - 6500. Retrieved 2013.
• 4、 Chazin, Walter J.,Colebrook, Lawrence D.. "Steric Influences on Spin-Lattice Relaxation Rates of Methyl Protons in Substituted Aromatic Molecules". . p. 597 - 604. Retrieved 1985.
• 5、 Dai, Xi-Jie,Li, Chao-Jun. "En Route to a Practical Primary Alcohol Deoxygenation". . p. 5433 - 5440. Retrieved 2016.
• 6、 Oriyama, Takeshi,Ichimura, Yuichi,Koga, Gen. "Stepwise Reduction of Acetals to the Corresponding Hydrocarbons. A Mild and Effective Transformation via Carbinyl Bromides". . p. 2581 - 2582. Retrieved 1991.
• 7、 Ouellet, étienne,Poirier, Donald. "Simple and efficient one-step conversion of benzonitrile into methylarene under mild conditions". . p. 2025 - 2028. Retrieved 2011.
• 8、 Lipschutz, Michael I.,Tilley, T. Don. "Carbon-carbon cross-coupling reactions catalyzed by a two-coordinate nickel(II)-Bis(amido) complex via observable NiI, NiII, and NiIII intermediates". . p. 7290 - 7294. Retrieved 2014.
• 9、 Crocella,Cerrato,Magnacca,Morterra,Cavani,Cocchi,Passeri,Scagliarini,Flego,Perego. "The balance of acid, basic and redox sites in Mg/Me-mixed oxides: The effect on catalytic performance in the gas-phase alkylation of m-cresol with methanol". . p. 125 - 135. Retrieved 2010.
• 10、 Kang, Qi-Kai,Li, Ke,Li, Yuntong,Lin, Yunzhi,Shi, Hang,Xu, Lun. "Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides". supporting information. p. 20391 - 20399. Retrieved 2021/08/13.