Esfenvalerate

Base Information

• Chemical Name: Esfenvalerate
• CAS No.: 66230-04-4
• Deprecated CAS: 72650-28-3
• Molecular Formula: C25H22ClNO3
• Molecular Weight: 419.908
• Hs Code.: 29269090
• European Community (EC) Number: 613-911-9
• ICSC Number: 1516
• UN Number: 3349
• UNII: 7F07OXM0PP
• DSSTox Substance ID: DTXSID4032667
• Wikipedia: Esfenvalerate
• Wikidata: Q424851
• Metabolomics Workbench ID: 56252
• ChEMBL ID: CHEMBL1891190
• Mol file: 66230-04-4.mol

Synonyms:alpha-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3- methylbutyrate;alpha-cyano-3-phenoxybenzyl alpha-isopropyl-4-chlorophenyl acetate;Belmark;esfenvalerate;fenvalarate;fenvalerate;Pydrin;pydrin, (R-(R*,R*))-isomer;pydrin, (R-(R*,S*))-isomer;pydrin, (S-(R*,R*))-isomer;pydrin, (S-(R*,S*))-isomer;S-5602;Sumi-alpha;Sumicidin;WL 43775

Chemical Property of Esfenvalerate

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 1.11E-11mmHg at 25°C
• Melting Point: 59 °C
• Refractive Index: 1.586
• Boiling Point: 538.9 °C at 760 mmHg
• Flash Point: 279.7 °C
• PSA: 59.32000
• Density: 1.21 g/cm³
• LogP: 6.67998
• Storage Temp.: 0-6°C
• Water Solubility.: 0.002 mg l-1 (25 °C)
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 419.1288213
• Heavy Atom Count: 30
• Complexity: 586

Purity/Quality:

99% ^*data from raw suppliers

Esfenvalerate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N
• Hazard Codes: T;N,N,T
• Statements: 23/25-43-50/53
• Safety Statements: 24-36/37/39-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C(C1=CC=C(C=C1)Cl)C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3
• Isomeric SMILES: CC(C)[C@@H](C1=CC=C(C=C1)Cl)C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the skin and respiratory tract. The substance is mildly irritating to the eyes. The substance may cause effects on the nervous system.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Description: Esfenvalerate is a synthetic pyrethoid insecticide – a class of pesticides originating from the chrysanthemum flower, which disrupt sodium channels. It has replaced fenvalerate, a less effective and more chronically toxic enantiomer. It can be used for general pest control, including spiders, fleas, scorpions, moths, beetles, etc. It is frequently applied on vegetable, nut, and non-crop products, often in combination with other active ingredients such as carbamate compounds and organophosphates. Product labels containing esfenvalerate include Sumi-Alpha, Hounddog, Sven, Asana, and Esfenvalerate 5EC, manufactured variously by BASF, Greencrop, and Standon.
• Uses: Esfenvalerate is the most potent insecticidal isomer of Fenvalerate (F279450), a pyrethroid insecticide used to control insects from food crops, animal feed and cotton products. Insecticide. Esfenvalerate possesses a broad range of insecticidal activity and it is used on cotton, fruit, vegetables and other crops.

Technology Process of Esfenvalerate

There total 15 articles about Esfenvalerate 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: 36.0%

sodium cyanide (143-33-9,25596-52-5) + S-(+)-2-(4-chlorophenyl)isovaleryl chloride (66230-05-5) + 3-Phenoxybenzaldehyde (39515-51-0) → esfenvalerate (66230-04-4,67890-40-8)

Guidance literature:

With N-butyl-N,N-dimethyl-(α-phenyl)ethylammonium bromide; In water; 1,2-dichloro-ethane; at 0 - 5 ℃; for 2.25h;

DOI:10.1081/SCC-120006462

Reference yield: 23.0%

α-cyano-3-phenoxybenzyl S-(+)-2-(4-chlorophenyl)isovalerate (956498-38-7,67890-40-8) → (R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate (67614-32-8,67890-40-8) + esfenvalerate (66230-04-4,67890-40-8)

Guidance literature:

With ammonia; In methanol; at -19 - 17 ℃; for 17 - 260h; Purification / work up; Resolution of racemate;

Reference yield:

racemic alpha-isopropyl-p-chlorophenylacetyl chloride + (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4,52315-06-7,61826-76-4,71962-66-8) → esfenvalerate (66230-04-4,67890-40-8)

Guidance literature:

With pyridine; In methanol; hexane; toluene;

upstream raw materials:

S-(+)-2-(4-chlorophenyl)isovaleryl chloride

(S)-m-phenoxybenzaldehyde cyanohydrin

2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride

Downstream raw materials:

1-allyl-4-chlorobenzene

4-chloro(ethylbenzene)

2-(4-Chlorophenyl)ethanol

2-(4-chlorophenyl)-3-methylbutyric acid

Refernces

• 1、 Reddy, Ch. Venkateshwar,Mahesh,Raju,Reddy, V.V. Narayana. "A new phase transfer catalyst and its applications in organic transformations". . p. 2797 - 2802. Retrieved 2007/10/03.
• 2、 Shan, Guomin,Stoutamire, Donald W.,Wengatz, Ingrid,Gee, Shirley J.,Hammock, Bruce D.. "Development of an immunoassay for the pyrethroid insecticide esfenvalerate". . p. 2145 - 2155. Retrieved 2007/10/03.