Anisole

Base Information

• Chemical Name: Anisole
• CAS No.: 100-66-3
• Molecular Formula: C7H8O
• Molecular Weight: 108.14
• Hs Code.: 29093090
• European Community (EC) Number: 202-876-1
• ICSC Number: 1014
• NSC Number: 7920
• UN Number: 2222
• UNII: B3W693GAZH
• DSSTox Substance ID: DTXSID4041608
• Nikkaji Number: J4.012F
• Wikipedia: Anisole
• Wikidata: Q312244,Q82914737,Q83049137
• Metabolomics Workbench ID: 46264
• ChEMBL ID: CHEMBL278024
• Mol file: 100-66-3.mol

Synonyms:anisol;anisole;methoxybenzene;methyl phenyl ether;phenyl methyl ether

Chemical Property of Anisole

Chemical Property:

• Appearance/Colour: Clear straw colored liquid
• Vapor Pressure: 10 mm Hg ( 42.2 °C)
• Melting Point: -37 °C
• Refractive Index: n20/D 1.516(lit.)
• Boiling Point: 153.599 °C at 760 mmHg
• Flash Point: 44.454 °C
• PSA: 9.23000
• Density: 0.953 g/cm³
• LogP: 1.69520
• Storage Temp.: Store at RT.
• Solubility.: 1.71g/l
• Water Solubility.: 1.6 g/L (20 ºC)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 108.057514874
• Heavy Atom Count: 8
• Complexity: 55.4
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Anisole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 10-38-20-36/37
• Safety Statements: 37/39-26-16-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: COC1=CC=CC=C1
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking.
• Uses: 1. Anisole is a solvent used in the synthesis of organic compounds and in large-scale applications such as the production of perfumes.2. GB2760-1996 stipulates it as allowable usable spices in food. It is mainly used for the preparation of vanilla, fennel and beer flavor.3. It is used for analyzing the reagents, solvents, and used for preparing perfumery and enteral pesticides.4. Anisole has been used directly in the synthesis of the marine pyrrole alkaloids polycitone A and B and the nonylphenol isomer 4-(3',6'-dimethyl-3-heptyl)phenol.5. It is used as solvents for recrystallization, fillers of thermostat, and used for measuring refractive index, as spices and organic synthesis intermediates. Anisole is widely used as a solvent for the synthesis of various organic compounds, anethole, nonylphenol isomer 4-(3',6'-dimethyl-3-heptyl)phenol, perfumes, insect pheromones and pharmaceuticals. It finds application in the preparation of inorganic complexes and materials such as tin-core/tin oxide nanoparticles.
• Production method: Anisole is produced through the reaction of methylating agent of dimethyl sulfate with phenol in alkaline aqueous solution. Phenol was mixed with sodium hydroxide solution, dimethyl sulfate was slowly added at below 10°C. And then heat to 40 °C, reflux for 18h, then stand for separation of the oil and dried with anhydrous calcium chloride, vacuum distillation to obtain anisole. It is derived by introducing the methyl chloride into the sodium phenol of liquid ammonia to react. It is generated from heating phenol and methanol. It is obtained from the reaction of phenol with dimethyl sulfate in the presence of sodium hydroxide.

Technology Process of Anisole

There total 1176 articles about Anisole 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: 63%

4-chloromethoxybenzene (623-12-1) + carbon dioxide (124-38-9,18923-20-1) → methoxybenzene (100-66-3) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

4-chloromethoxybenzene; With bis(cyclopentadienyl)titanium dichloride; butyl magnesium bromide; In tetrahydrofuran; at 40 ℃; for 6h; Inert atmosphere; Schlenk technique;

carbon dioxide; In tetrahydrofuran; at 20 ℃; for 2h; Solvent; Reagent/catalyst; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.organomet.9b00712

Reference yield: 62%

carbon monoxide (201230-82-2) + para-iodoanisole (696-62-8) → bis(p-methoxyphenyl)methanone (90-96-0) + methoxybenzene (100-66-3) + 4-methoxybenzoic acid (100-09-4) + 1,2-bis(4-methoxyphenyl)-1,2-ethanedione (1226-42-2)

Guidance literature:

With sodium hydroxide; iron pentacarbonyl; tetrabutylammomium bromide; In water; benzene; at 70 ℃; for 48h; Further byproducts given;

Reference yield: 26%

N-Nitroso-N-benzylformamide (85995-49-9) + 4-methoxyphenyl magnesium bromide (13139-86-1) → benzyl bromide (100-39-0) + methoxybenzene (100-66-3)

Guidance literature:

In diethyl ether; at -3 - 0 ℃; for 1.5h; Product distribution; var. temp.;

DOI:10.1021/jo00163a012

upstream raw materials:

tetrahydrofuran

sodium acetate

para-methoxyphenyldiazonium chloride

diazomethane

Downstream raw materials:

4-Methoxyphenethylamine

4-hydroxy-1-(4-methoxyphenyl)-butan-1-one

4-(bis(4-methoxyphenyl)methyl)pyridine

(E)-4-(4-methoxyphenyl)-4-oxo-2-butenoic acid

Refernces

• 1、 Lin, Yi,Ridge, D. P.,Munson, Burnaby. "Association Reactions of Trimethylsilyl Ions". . p. 550 - 558. Retrieved 1991.
• 2、 Nelson,Gribble. "-". . p. 1425. Retrieved 1974.
• 3、 Solvhoj, Amanda,Madsen, Robert. "Dehydrogenative coupling of primary alcohols to form esters catalyzed by a ruthenium N-heterocyclic carbene complex". . p. 6044 - 6048. Retrieved 2011.
• 4、 Wicht, Richard,Bahnmüller, Stefanie,Brandhorst, Kai,Schweyen, Peter,Br?ring, Martin. "Cationic nickel porphyrinoids with unexpected reactivity". . p. 583 - 588. Retrieved 2016.
• 5、 Langlois, Bernard R.,Roques, Nicolas. "Nucleophilic trifluoromethylation of aryl halides with methyl trifluoroacetate". . p. 1318 - 1325. Retrieved 2007.
• 6、 Hashmi, A. Stephen K.,Ramamurthi, Tanuja Dondeti,Todd, Matthew H.,Tsang, Althea S.-K.,Graf, Katharina. "Gold-catalysis: Reactions of organogold compounds with electrophiles". . p. 1619 - 1626. Retrieved 2010.
• 7、 Koppang, Miles D.,Woolsey, Neil F.,Bartak, Duane E.. "Carbon-Oxygen Bond Cleavage Reactions by Electron Transfer. 1. Electrochemical Studies on the Formation and Subsequent Reaction Pathways of Cyanoanisole Radical Anions". . p. 2799 - 2805. Retrieved 1984.
• 8、 Climent, Maria Jose,Corma, Avelino,Iborra, Sara,Mifsud, Maria. "Heterogeneous palladium catalysts for a new one-pot chemical route in the synthesis of fragrances based on the Heck reaction". . p. 1949 - 1954. Retrieved 2007.
• 9、 Shiraishi, Yasuhiro,Takeda, Yoshinori,Sugano, Yoshitsune,Ichikawa, Satoshi,Tanaka, Shunsuke,Hirai, Takayuki. "Highly efficient photocatalytic dehalogenation of organic halides on TiO2 loaded with bimetallic Pd-Pt alloy nanoparticles". . p. 7863 - 7865. Retrieved 2011.
• 10、 Dunsford, Jay J.,Cavell, Kingsley J.. "Pd-PEPPSI-type expanded ring N-heterocyclic carbene complexes: Synthesis, characterization, and catalytic activity in Suzuki-Miyaura cross coupling". . p. 2902 - 2905. Retrieved 2014.