Furamethrin

Base Information

• Chemical Name: Furamethrin
• CAS No.: 23031-38-1
• Deprecated CAS: 23031-15-4,51496-89-0,8064-25-3,39322-34-4,51496-89-0,8064-25-3
• Molecular Formula: C₁₈H₂₂O₃
• Molecular Weight: 286.371
• DSSTox Substance ID: DTXSID9058028
• Nikkaji Number: J27.278G
• Wikidata: Q27155604
• Metabolomics Workbench ID: 144197
• Mol file: 23031-38-1.mol

Synonyms:FURAMETHRIN;23031-38-1;Prothrin;Pynamin D forte;Pynamin D;Furamethrin, racemic-;CCRIS 3281;5-Propargylfurfuryl chrysanthemate;AI3-27972;5-(2-Propynyl)-2-furfuryl chrysanthemumcarboxylate;(5-prop-2-ynylfuran-2-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;5-Propargyl-2-furylmethyl dl-cis,trans-chrysanthemate;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, 5-(2-propynyl)furfuryl ester;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (5-(2-propynyl)-2-furanyl)methyl ester, cis,trans-(+/-)-;SCHEMBL8822206;DTXSID9058028;CHEBI:81795;LS-58723;LS-58724;LS-58725;C18506;Q27155604;[5-(prop-2-yn-1-yl)furan-2-yl]methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, [5-(2-propyn-1-yl)-2-furanyl]methyl ester;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, [5-(2-propynyl)-2-furanyl]methyl ester;Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-,5-(2-propynyl)furfuryl ester

Chemical Property of Furamethrin

Chemical Property:

• Vapor Pressure: 6.94E-05mmHg at 25°C
• Refractive Index: 1.557
• Boiling Point: 343.7°Cat760mmHg
• Flash Point: 161.6°C
• PSA: 39.44000
• Density: 1.109g/cm³
• LogP: 3.73690
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 286.15689456
• Heavy Atom Count: 21
• Complexity: 476

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1C(C1(C)C)C(=O)OCC2=CC=C(O2)CC#C)C
• Uses: Furamethrin is a synthetic pyrethroid insecticide which is very effective against the yellow fever mosquito Aedes aegypti.

Technology Process of Furamethrin

There total 9 articles about Furamethrin 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: 84.0%

(±)-cis- and (±)-trans-{5-[3-(trimethylsilyl)prop-2-yn-1-yl]furan-2-yl}methyl-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate (1531604-80-4) → furamethrin (23031-38-1,23031-15-4,51496-89-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -20 ℃; for 0.25h;

DOI:10.1021/jf4045843 DOI:10.1021/jf4045843

Reference yield:

3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride (4489-12-7,4489-14-9,26770-95-6,28684-92-6,34909-52-9,51348-74-4,53955-46-7,56650-12-5,14297-81-5) + 5-propargyl-furfuryl alcohol (3311-29-3) → furamethrin (23031-38-1,23031-15-4,51496-89-0)

Guidance literature:

Reference yield:

2-(chloromethyl)-5-(dibutoxymethyl)furan (126080-78-2) → furamethrin (23031-38-1,23031-15-4,51496-89-0)

Guidance literature:

Multi-step reaction with 5 steps

1: copper(l) iodide; potassium carbonate / acetonitrile / 55 °C / Inert atmosphere

2: hydrogenchloride / water / 2 h

3: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C

4: benzene / 5 h / Inert atmosphere; Reflux

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / -20 °C

With hydrogenchloride; sodium tetrahydroborate; copper(l) iodide; tetrabutyl ammonium fluoride; potassium carbonate; In tetrahydrofuran; methanol; water; acetonitrile; benzene;

DOI:10.1021/jf4045843

upstream raw materials:

3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride

5-propargyl-furfuryl alcohol

2-(hydroxymethyl)-5-[3-(trimethylsilyl)prop-2-yn-1-yl]furan

(±)-cis- and (±)-trans-{5-[3-(trimethylsilyl)prop-2-yn-1-yl]furan-2-yl}methyl-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

Refernces

• 1、 Chang, Fei,Dutta, Saikat,Becnel, James J.,Estep, Alden S.,Mascal, Mark. "Synthesis of the insecticide prothrin and its analogues from biomass-derived 5-(Chloromethyl)furfural". . p. 476 - 480. Retrieved 2015/04/22.