Anethole

Base Information

• Chemical Name: Anethole
• CAS No.: 104-46-1
• Deprecated CAS: 12002-40-3,8022-08-0,109957-71-3,57131-42-7
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• Hs Code.: 2909309090
• European Community (EC) Number: 224-052-0,288-194-5,256-753-2,203-205-5
• NSC Number: 758626,209529,4018
• UN Number: 1993
• UNII: Q3JEK5DO4K
• DSSTox Substance ID: DTXSID9020087
• Nikkaji Number: J4.026F,J61.645A
• Wikipedia: Anethole
• Wikidata: Q255564
• NCI Thesaurus Code: C76862
• RXCUI: 17881
• Metabolomics Workbench ID: 55161
• ChEMBL ID: CHEMBL452630
• Mol file: 104-46-1.mol

Synonyms:Anise camphor;Isoestragole;NSC 4018;Nauli gum;Oil of aniseed;p-1-Propenylanisole;p-Anethole;p-Methoxy-b-methylstyrene;p-Propenylanisole;p-Propenylphenyl methyl ether;Anisole,p-propenyl- (8CI);Benzene, 1-methoxy-4-(1-propenyl)- (9CI);1-Methoxy-4-(1-propenyl)benzene;1-Methoxy-4-propenylbenzene;1-Propene,1-(4-methoxyphenyl)-;4-(1-Propenyl)anisole;4-Methoxy-1-propenylbenzene;4-Methoxypropenylbenzene;4-Propenylanisole;Anethol;

Chemical Property of Anethole

Chemical Property:

• Appearance/Colour: Colourless,clear, liquid
• Melting Point: 20-21 °C(lit.)
• Refractive Index: n20/D 1.561(lit.)
• Boiling Point: 237.5 °C at 760 mmHg
• Flash Point: 88.4 °C
• PSA: 9.23000
• Density: 0.988 g/mL at 25 °C(lit.)
• LogP: 2.72830
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 148.088815002
• Heavy Atom Count: 11
• Complexity: 121
• Transport DOT Label: Combustible Liquid

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: CC=CC1=CC=C(C=C1)OC
• Isomeric SMILES: C/C=C/C1=CC=C(C=C1)OC

Technology Process of Anethole

There total 78 articles about Anethole 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: 86.0%

C16H22N2O → 3,4,5-Trimethylpyrazole (5519-42-6) + anethole (104-46-1,25086-72-0,63589-56-0)

Guidance literature:

With organo lithium reagent; In hexane; at 20 ℃; for 24h;

DOI:10.1021/acs.orglett.6b03522

Reference yield: 80.0%

1-bromo-1-propene (590-14-7) + 4-methoxyphenylmagnesium chloride (699-19-4) → anethole (104-46-1,25086-72-0,63589-56-0)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; cobalt acetylacetonate; In tetrahydrofuran; at 15 - 20 ℃; for 0.25h;

DOI:10.1016/S0040-4039(98)01266-0

Reference yield: 79.0%

4-methoxycinnamaldehyde (1963-36-6) → anethole (104-46-1,25086-72-0,63589-56-0)

Guidance literature:

With manganese; (1,2-dimethoxyethane)dichloronickel(II); 1,1,3,3-Tetramethyldisiloxane; potassium tert-butylate; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate; In toluene; at 70 ℃; for 5h;

DOI:10.1021/acscatal.1c03980

upstream raw materials:

pyridine

1-(4-methoxyphenyl)prop-1-yl acetate

Estragole

acetic anhydride

Downstream raw materials:

1-acetoxy-1-(4-methoxy-phenyl)-2-methyl-3-piperidino-propane

4-(2-nitro-propenyl)-anisole

5-(4-methoxy-phenyl)-6-methyl-8-oxo-5,6-dihydro-8H-imidazo[5,1-c][1,4]oxazine-1-carboxylic acid methyl ester

(2S,4S,5S,6R)-4-(4-Methoxy-phenyl)-5-methyl-2,6-di-p-tolyl-[1,3]dioxane

Refernces

• 1、 Yuan, Chunchen,Tu, Guangliang,Zhao, Yingsheng. "Rhodium(III)-Catalyzed Selective Monoarylation of β or γ C(sp3)-H Bonds Assisted by a Trimethylpyrazole Group". . p. 356 - 359. Retrieved 2017.
• 2、 Malchau, Christian,Loose, Florian,Mees, Yannick,Duppe, Jens,Sun, Yu,Niedner-Schatteburg, Gereon,Thiel, Werner R.. "Electronic properties of a cationic triphenylphosphine ligand decorated with a (η5-C5H5)Fe group in late-transition-metal complexes". . p. 3335 - 3343. Retrieved 2020.
• 3、 Neumann, Ronny,Sasson, Yoel. "Mechanism of Base-Catalyzed Reactions in Phase-Transfer-Systems with Poly(ethylene glycols) as Catalysts. The Isomerization of Allylanisole". . p. 3448 - 3451. Retrieved 1984.
• 4、 Dellacoletta,Shechter. "-". . p. 4817,4818,4820. Retrieved 1979.
• 5、 Higman, Carolyn S.,Lanterna, Anabel E.,Marin, M. Luisa,Scaiano, Juan C.,Fogg, Deryn E.. "Catalyst Decomposition during Olefin Metathesis Yields Isomerization-Active Ruthenium Nanoparticles". . p. 2446 - 2449. Retrieved 2016.
• 6、 Keaveney,Pappas. "-". . p. 841. Retrieved 1969.
• 7、 Garcia, Marco A. S.,Heyder, Rodrigo S.,Oliveira, Kelley C. B.,Costa, Jean C. S.,Corio, Paola,Gusevskaya, Elena V.,dos Santos, Eduardo N.,Bazito, Reinaldo C.,Rossi, Liane M.. "Support Functionalization with a Phosphine-Containing Hyperbranched Polymer: A Strategy to Enhance Phosphine Grafting and Metal Loading in a Hydroformylation Catalyst". . p. 1951 - 1960. Retrieved 2016.
• 8、 Meng, Lingpu,Yang, Jingjie,Duan, Mei,Wang, You,Zhu, Shaolin. "Facile Synthesis of Chiral Arylamines, Alkylamines and Amides by Enantioselective NiH-Catalyzed Hydroamination". supporting information. p. 23584 - 23589. Retrieved 2021/09/28.
• 9、 Shu, Xiao,Jiang, Yuan-Yuan,Kang, Lei,Yang, Luo. "Ni-Catalyzed hydrocyanation of alkenes with formamide as the cyano source". supporting information. p. 2734 - 2738. Retrieved 2020/06/17.