Anethole

Base Information

• Chemical Name: Anethole
• CAS No.: 4180-23-8
• Deprecated CAS: 12002-40-3,8022-08-0,109957-71-3,57131-42-7
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• Hs Code.: 29093090
• 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: 4180-23-8.mol

Synonyms:1-(4-methoxyphenyl)propene;1-methoxy-4-(1-propenyl)benzene;anethole;anethole, (E)-isomer;anethole, (Z)-isomer;p-propenylanisole;trans-anethole

Chemical Property of Anethole

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow liquid
• Vapor Pressure: 1.33 hPa (63 °C)
• 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: 0.959 g/cm³
• LogP: 2.72830
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in benzene, ethyl acetate, acetone, carbon disulfide.
• Water Solubility.: practically insoluble
• 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

Anethole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N
• Statements: 43-51/53
• Safety Statements: 36/37-61

MSDS Files:

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
• General Description: **Conclusion:** trans-Anethole is a compound that undergoes photoinduced electron transfer reactions, leading to isomerization, dimerization, and oxygenation when irradiated in the presence of electron acceptors. The isomerization occurs via triplet-state formation, while dimerization proceeds through a quasi-concerted [2 + 1] cycloaddition of cation radicals, yielding cyclobutane dimers. Oxygen inhibits these processes, instead promoting the formation of oxygenated products like p-anisaldehyde. The study rules out the involvement of an acyclic 1,4-cation radical in these reactions, as no [2 + 4] dimers or 1,2-dioxanes are observed.

Technology Process of Anethole

There total 126 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: 99.0%

Estragole (140-67-0) → E-1-(4'-methoxyphenyl)prop-1-ene (4180-23-8,25086-72-0,63589-56-0)

Guidance literature:

With Polystyrene-supported 4-tert-butyl-2-(diisopropylphosphino)-1H-imidazole and ruthenium complex; In [⁽²⁾H₆]acetone; at 25 ℃; for 0.166667h; Reagent/catalyst; stereoselective reaction; Inert atmosphere; Glovebox;

DOI:10.1021/ol500327k

Reference yield: 99.0%

cis-Anethole (25679-28-1,25086-72-0,63589-56-0) → E-1-(4'-methoxyphenyl)prop-1-ene (4180-23-8,25086-72-0,63589-56-0)

Guidance literature:

cis-Anethole; With cobalt(II) chloride; 2,2'-bis(diphenylphosphino)diphenylamine; In toluene; at 20 ℃; for 0.0833333h; Schlenk technique; Inert atmosphere;

With sodium triethylborohydride; In toluene; at 20 ℃; for 1h; Reagent/catalyst; diastereoselective reaction; Catalytic behavior; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00072

Reference yield: 97.0%

1-bromo-4-methoxy-benzene (104-92-7) + potassium trifluoro(prop-1-en-2-yl)borate → E-1-(4'-methoxyphenyl)prop-1-ene (4180-23-8,25086-72-0,63589-56-0)

Guidance literature:

With potassium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In water; isopropyl alcohol; at 120 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

upstream raw materials:

Estragole

4-(3-chloro-allyl)-anisole

ethylmagnesium iodide

4-methoxy-benzaldehyde

Downstream raw materials:

(+/-)-erythro-1-chloro-2-(2.4-dinitro-phenylsulfanyl)-1-(4-methoxy-phenyl)-propane

p-methoxy-α-methylcinnamaldehyde

(E)-1-(4-hydroxyphenyl)propene

4-Propenyl-phenol

Refernces

Electron Transfer Induced Photoisomerization, Dimerization, and Oxygenation of trans- and cis-Anethole. The Role of Monomer and Dimer Cation Radicals

10.1021/ja00234a014

The study investigates the photoinduced electron transfer reactions of trans-anethole (t-A) and cis-anethole (c-A), focusing on their isomerization, dimerization, and oxygenation processes. When irradiated in the presence of electron acceptors like 9-cyanoanthracene (CA) or 9,10-dicyanoanthracene (DCA), both t-A and c-A undergo trans,cis isomerization and dimerization to form various cyclobutane dimers, with the dimer ratio being sensitive to reaction conditions. The presence of oxygen quenches isomerization and dimerization, leading to the formation of oxygenated products like p-anisaldehyde. The study concludes that isomerization occurs via reverse electron transfer to generate triplet anethole, while dimerization proceeds via quasi-concerted [2 + 1] cycloaddition of cation radicals. The results also suggest that an acyclic 1,4-cation radical is not involved in these reactions, as no [2 + 4] dimers or 1,2-dioxanes are detected.