Estragole

Base Information

• Chemical Name: Estragole
• CAS No.: 140-67-0
• Deprecated CAS: 1407-27-8,77525-18-9
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• Hs Code.: 2909309090
• European Community (EC) Number: 205-427-8
• NSC Number: 404113
• UNII: 9NIW07V3ET
• DSSTox Substance ID: DTXSID0020575
• Nikkaji Number: J5.794K
• Wikipedia: Estragole
• Wikidata: Q419495
• Metabolomics Workbench ID: 46370
• ChEMBL ID: CHEMBL470671
• Mol file: 140-67-0.mol

Synonyms:4-allylanisole;estragole;methyl chavicol;p-allylanisole

Chemical Property of Estragole

Chemical Property:

• Appearance/Colour: colourless liquid with an aniseed smell
• Vapor Pressure: 0.21mmHg at 25°C
• Melting Point: 28-35 °C
• Refractive Index: n20/D 1.521(lit.)
• Boiling Point: 216 °C at 760 mmHg
• Flash Point: 81.1 °C
• PSA: 9.23000
• Density: 0.938 g/cm³
• LogP: 2.42370
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 148.088815002
• Heavy Atom Count: 11
• Complexity: 112

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: R22:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: COC1=CC=C(C=C1)CC=C

Technology Process of Estragole

There total 138 articles about Estragole 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: 70.0%

4-methoxyphenethyl bromide (14425-64-0) + trimethylsulphonium iodide (2181-42-2) → 4-Methoxystyrene (637-69-4,24936-44-5) + Estragole (140-67-0)

Guidance literature:

With n-butyllithium; lithium iodide; In tetrahydrofuran; hexane; from 0 degC to room temp.;

DOI:10.1016/S0040-4039(00)73523-4

Reference yield: 65.0%

4-chloromethoxybenzene (623-12-1) + allyl-trimethyl-silane (762-72-1) → Estragole (140-67-0) + methoxybenzene (100-66-3)

Guidance literature:

In water; acetonitrile; for 3.58333h; Concentration; Irradiation; Flow reactor;

DOI:10.1002/adsc.201600019

Reference yield: 60.0%

1-bromo-4-methoxy-benzene (104-92-7) + Allyl acetate (591-87-7) → Estragole (140-67-0) + 4,4'-Dimethoxybiphenyl (2132-80-1) + methoxybenzene (100-66-3)

Guidance literature:

With bromobenzene; zinc dibromide; zinc; acetic acid; cobalt(II) bromide; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1021/ol0340641

upstream raw materials:

allyl iodid

(4-methoxyphenyl)magnesium iodide

4-(3-chloro-allyl)-anisole

3-(p-methoxyphenyl)-1-propanol

Downstream raw materials:

4-(prop-2-enyl)phenol

4-Methoxyphenylacetic acid

cis-Anethole

4-Methoxyphenylacetaldehyde

Refernces

• 1、 Jeffery. "Tetraalkylammonium salt-based catalyst systems for directing Heck-type reactions. Arylation of allyltrimethylsilane". . p. 8445 - 8449. Retrieved 2000.
• 2、 Martinez-Arranz, Sheila,Carrera, Nora,Albeniz, Ana C.,Espinet, Pablo,Vidal-Moya, Alejandro. "Batch stille coupling with insoluble and recyclable stannylated polynorbornenes". . p. 3551 - 3560. Retrieved 2012.
• 3、 Kotha, Sambasivarao,Behera, Manoranjan,Shah, Vrajesh R.. "A simple synthetic approach to allylated aromatics via the Suzuki-Miyaura cross-coupling reaction". . p. 1877 - 1880. Retrieved 2005.
• 4、 Martínez-Arranz, Sheila,Presa-Soto, David,Carriedo, Gabino A.,Presa Soto, Alejandro,Albéniz, Ana C.. "Polyphosphazenes for the Stille reaction: A new type of recyclable stannyl reagent". . p. 2227 - 2236. Retrieved 2016.
• 5、 Fiorio, Jhonatan L.,Rossi, Liane M.. "Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold". . p. 312 - 318. Retrieved 2021/01/29.
• 6、 Yoo, Byung Woo,Kim, Jung Youn. "Selective and efficient desulfurization of thiiranes with Mo(CO)6". . p. 13 - 18. Retrieved 2019/08/26.