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Anisole

Base Information Edit
  • 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
Anisole

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

Suppliers and Price of Anisole
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Anisole
  • 500g
  • $ 130.00
  • TRC
  • Anisole
  • 250g
  • $ 110.00
  • TCI Chemical
  • Anisole
  • 25G
  • $ 18.00
  • TCI Chemical
  • Anisole
  • 500G
  • $ 34.00
  • TCI Chemical
  • Anisole min. 99.0 %
  • 5G
  • $ 10.00
  • Sigma-Aldrich
  • Anisole ReagentPlus?, 99%
  • 18 L
  • $ 1200.00
  • Sigma-Aldrich
  • Anisole ReagentPlus , 99%
  • 18l-cs
  • $ 1160.00
  • Sigma-Aldrich
  • Anisole Anisole for synthesis. CAS No. 100-66-3, EC Number 202-876-1., for synthesis
  • 8014529025
  • $ 857.00
  • Sigma-Aldrich
  • Anisole for synthesis
  • 25 L
  • $ 820.47
  • Sigma-Aldrich
  • Anisole United States Pharmacopeia (USP) Reference Standard
  • 3x1.2ml
  • $ 366.00
Total 35 raw suppliers
Chemical Property of Anisole Edit
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:

99.0%Min *data from raw suppliers

Anisole *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn 
  • 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:
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
Guidance literature:
With sodium hydroxide; iron pentacarbonyl; tetrabutylammomium bromide; In water; benzene; at 70 ℃; for 48h; Further byproducts given;
Guidance literature:
In diethyl ether; at -3 - 0 ℃; for 1.5h; Product distribution; var. temp.;
DOI:10.1021/jo00163a012
Refernces Edit

Acidity versus metal-induced Lewis acidity in zeolites for Friedel–Crafts acylation

10.1016/j.crci.2016.03.008

This research investigates the impact of metal-induced Lewis acidity on the catalytic activity of zeolites in the Friedel-Crafts acylation of anisole with propanoic acid. The study prepared acid catalysts including Ni, Ag, and Fe-loaded zeolites of different structures (BEA and MFI) via cationic exchange or impregnation techniques from pristine H-zeolites. The results showed that regardless of the doping procedure, the introduction of transition metals led to a significant decrease in propanoic acid conversion, with the detrimental effect following the order: Ag? > Ni2? > Fe3?. In contrast, pristine acidic zeolites, particularly H-ZSM-5, were found to be the most active and selective, with the highest intrinsic activity (TOF values of 0.09 h?1).

Designing a catalytic synthesis of 4-methylcoumarin from ortho-iodophenyl 3-butenoate: Ring closure and isomerization control

10.1016/S0022-328X(96)06489-3

The research investigates the catalytic synthesis of 4-methylcoumarin from ortho-iodophenyl 3-butenoate using palladium complexes. The purpose is to control the ring closure and isomerization processes to achieve high yields of the desired cyclic compound. Key chemicals involved include palladium(0) complexes, such as Pd(dba)2 and Pd(PPh3)4, along with ligands like triphenylphosphine and bis(diphenylphosphino)ferrocene (dppf), solvents like anisole and dimethylformamide (DMF), and neutralizing agents like potassium butyrate and magnesium oxide. The study concludes that by carefully selecting ligands, solvents, and neutralizing agents, and by controlling reaction conditions, it is possible to achieve quantitative yields of 4-methylcoumarin. Specifically, the use of dppf in conjunction with Pd(PPh3)4 in DMF with MgO under nitrogen resulted in a 100% yield of the desired product, demonstrating effective control over the competing reactions.

Trifluoromethylation of Benzoic Acids: An Access to Aryl Trifluoromethyl Ketones

10.1021/acs.orglett.1c01720

The study presents an efficient method for the trifluoromethylation of benzoic acids using TMSCF3 (trimethylsilyl trifluoromethane) to produce aryl trifluoromethyl ketones. The reaction involves anhydrides as in situ activating reagents, with trifluoroacetic anhydride (TFAA) and 4-dimethylaminopyridine (DMAP) playing crucial roles in activating the carboxylic acids and facilitating nucleophilic addition. CsF (cesium fluoride) is used to enhance the yield of the desired products. The reaction is conducted in PhOMe (anisole) solvent under nitrogen at 120 °C for 15 hours. The study demonstrates a wide substrate scope, including various carboxylic acids with different functional groups, and shows high functional group tolerance. Notably, bioactive molecules such as adapalin, probenecid, and telmisartan can also be trifluoromethylated using this method, highlighting its potential in drug design and development. The reaction conditions are relatively mild, and the process is scalable, making it a practical and environmentally benign approach for synthesizing aryl trifluoromethyl ketones.

Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins

10.7164/antibiotics.53.1305

The study focuses on the synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins. Cephalosporins are widely used antibiotics, but many have become ineffective against respiratory tract infections due to resistance issues, particularly from penicillin-resistant Streptococcus pneumoniae (PRSP). To address this, researchers introduced a vinyl spacer at the C-3 position of the cephem nucleus and synthesized new cephalosporins with a C(3) substituted aminopyrimidinyl group. The synthesis involved coupling acid 3 with 7-ACLE in the presence of pyridine and phosphorous oxychloride to form intermediate 5, which was then reacted with nucleophiles (pyrimidinylthiol group) in DMF. The protecting groups were removed using trifluoroacetic acid (TFA) and anisole to obtain the final cephalosporins. Another series of compounds was prepared from chloride 5 via allyl chloride 6, using a Wittig reagent and subsequent displacement reactions. The synthesized compounds were tested for their antibacterial activities against various bacterial strains, including Gram-positive and Gram-negative bacteria, and showed improved activities against respiratory tract pathogens compared to the reference antibiotic cefdinir.

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