Ethyl chrysanthemate

Base Information

• Chemical Name: Ethyl chrysanthemate
• CAS No.: 97-41-6
• Molecular Formula: C12H20O2
• Molecular Weight: 196.29
• Hs Code.: 29162090
• European Community (EC) Number: 202-579-7
• NSC Number: 10819
• DSSTox Substance ID: DTXSID2052651
• Nikkaji Number: J23.507E
• Wikidata: Q72473877
• Metabolomics Workbench ID: 123690
• ChEMBL ID: CHEMBL1596099
• Mol file: 97-41-6.mol

Synonyms:chrysanthemic acid ethyl ester;ethyl chrysanthemate;ethyl chrysanthemate, (cis)-isomer;ethyl chrysanthemate, (trans)-isomer;ethyl chrysanthemate, cis(+-)-isomer;ethyl chrysanthemate, trans(+-)-isomer

Chemical Property of Ethyl chrysanthemate

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 0.0372mmHg at 25°C
• Melting Point: 0oC
• Refractive Index: n20/D 1.461(lit.)
• Boiling Point: 240.8 °C at 760 mmHg
• Flash Point: 84.4 °C
• PSA: 26.30000
• Density: 0.991 g/cm³
• LogP: 2.78790
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 196.146329876
• Heavy Atom Count: 14
• Complexity: 260

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl chrysanthemate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1C(C1(C)C)C=C(C)C
• Uses: Ethyl Chrysanthemate is an organic building block used in the synthesis of various chemical compounds, such as insecticide, Resmethrin (R144685). It is used in the preparation of trans-norchrysanthemates and trans-norpyrethrates, having insecticidal activity.

Technology Process of Ethyl chrysanthemate

There total 67 articles about Ethyl chrysanthemate 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: 92.0%

2,5-Dimethyl-2,4-hexadiene (764-13-6) + GlyOEt*HCl (459-73-4) → ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate (97-41-6)

Guidance literature:

GlyOEt*HCl; With acetic acid; carbonic acid dimethyl ester; at 20 - 28 ℃; pH=3.5 - 4.53; Large scale;

2,5-Dimethyl-2,4-hexadiene; With copper(l) chloride; at 90 - 95 ℃; Large scale;

Reference yield: 91.0%

diazoacetic acid ethyl ester (623-73-4) + 2,5-Dimethyl-2,4-hexadiene (764-13-6) → ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate (97-41-6) + diethyl Fumarate (623-91-6) + Diethyl maleate (141-05-9)

Guidance literature:

hexarhodium hexadecacarbonyl; at 60 ℃; for 7h;

DOI:10.1016/S0040-4039(01)90438-1

Reference yield: 89.6%

diazoacetic acid ethyl ester (623-73-4) + 2,5-Dimethyl-2,4-hexadiene (764-13-6) → ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate (97-41-6)

Guidance literature:

K-PFIEP[SO₃ H]; In dichloromethane;

upstream raw materials:

diazoacetic acid ethyl ester

2,5-Dimethyl-2,4-hexadiene

ethyl 3-methylbut-2-enoate

prenyl tolyl sulfone

Downstream raw materials:

chrysanthemol

ethyl trans-(+/-)-chrysanthemate

2,2-Dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid 2-benzyl-furan-3-ylmethyl ester

resmethrin

Refernces

• 1、 -. "Synthesis Method of Cyclopropane or Cyclopentene Derivatives via Fe-catalyzed Cationic Radical Cycloaddition Reaction". Paragraph 0080-0081; 0101-0102. . Retrieved 2021/11/02.
• 2、 Cho, Yong Hyun,Kim, Jae Hyung,An, Hyeju,Ahn, Kwang-Hyun,Kang, Eun Joo. "Cycloaddition Reactions of Alkene Radical Cations using Iron(III)-Phenanthroline Complex". supporting information. p. 2183 - 2188. Retrieved 2020/04/29.