Fenvalerate

Base Information

• Chemical Name: Fenvalerate
• CAS No.: 51630-58-1
• Deprecated CAS: 131641-62-8
• Molecular Formula: C25H22ClNO3
• Molecular Weight: 419.908
• Hs Code.: 2926909036
• European Community (EC) Number: 257-326-3
• ICSC Number: 0273
• UN Number: 2811,3352,2765
• UNII: Z6MXZ39302
• DSSTox Substance ID: DTXSID101017940
• Nikkaji Number: J3.515G
• Wikipedia: Fenvalerate
• Wikidata: Q412010
• NCI Thesaurus Code: C65672
• ChEMBL ID: CHEMBL492491
• Mol file: 51630-58-1.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 Fenvalerate

Chemical Property:

• Appearance/Colour: clear viscious yellow liquid
• Vapor Pressure: 1.11E-11mmHg at 25°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.: −20°C
• Water Solubility.: Soluble in 100% ethanol (>25 mg/ml), water (0.001 g/L) at 20°C, and DMSO.
• 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
• Transport DOT Label: Poison

Purity/Quality:

99.9% ^*data from raw suppliers

Fenvalerate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N
• Hazard Codes: T,N
• Statements: 25-36/37/38-50/53-57
• Safety Statements: 26-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Pyrethrins/Pyrethroids
• Canonical SMILES: CC(C)C(C1=CC=C(C=C1)Cl)C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the nervous system.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Description: Fenvalerate is a yellow-brown viscous liquid that is practically soluble in water. It is stable to moderate heat and light and is rapidly hydrolysed in basic environments (above pH 8). Fenvalerate is a racemic mixture of four stereoisomers in equal proportions owing to the presence of two chiral centres. It is a synthetic type II pyrethroid. Fenvalerate is registered as an insecticide for a wide array of crop uses, as well as a termiticide and insect repellent.
• Uses: Insecticide used against a wide variety of pests. An insecticide, used to control insects from food crops, animal feed and cotton products. Fenvalerate controls a wide range of insect pests in fruit, vines, olives, hops, nuts, vegetables, cotton, oilseed rape, sunflowers, alfalfa, cereals, maize, sorghum, potatoes, beets, soyabeans, tobacco, sugar cane and ornamentals. It is also used in public health situations and in animal houses.

Technology Process of Fenvalerate

There total 19 articles about Fenvalerate 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%

sodium hydrogencarbonate (144-55-8) + 2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride (51631-50-6) + 3-Phenoxybenzaldehyde (39515-51-0) → FENVALERATE (51630-58-1,67890-40-8)

Guidance literature:

In n-heptane; water;

Reference yield: 94.7%

2-hydroxy-2-(3-phenoxyphenyl)acetonitrile (39515-47-4) + 2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride (51631-50-6) → FENVALERATE (51630-58-1,67890-40-8)

Guidance literature:

In pyridine; benzene;

DOI:10.1007/BF00956606

Reference yield: 91.0%

2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride (51631-50-6) + 3-Phenoxybenzaldehyde (39515-51-0) → FENVALERATE (51630-58-1,67890-40-8)

Guidance literature:

In tetrahydrofuran; n-heptane; water;

upstream raw materials:

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

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

para-chlorotoluene

3-Methyl-2-(4'-chlorophenyl)-butyronitrile

Downstream raw materials:

4'-hydroxyfenvalerate

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

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

Refernces

Novel Synthesis and Insecticideal Activity of MTI-800, Desfluoro MTI-800 and Their Intermediates

10.1002/ps.2780450411

The research aimed to develop a novel synthesis route for the insecticides MTI-800 and desfluoro MTI-800, and to evaluate their insecticidal activities against the tobacco caterpillar Spodoptera litura. The study utilized a tandem Friedel-Crafts acylation and other chemical reactions, diethyl sulfate played a crucial role as a reagent in the alkylation step of the synthesis process. Specifically, it was used to convert the phenolic compound 3-(4-hydroxyphenyl)-3-methyl-2-butanone (2) into 3-(4-ethoxyphenyl)-3-methyl-2-butanone (3). The synthesis process included multiple steps, including acylation, alkylation, aldol condensation, reduction, chlorination, and hydrogenation, to produce the target compounds and their intermediates. The results showed that MTI-800 (7b) and desfluoro MTI-800 (7a) exhibited excellent insecticidal activity comparable to the well-known synthetic pyrethroids fenvalerate and cypermethrin. The study concluded that the central link structure and the presence of a fluoro substitution significantly influenced the insecticidal activity, with the alkane central link showing high activity regardless of the fluoro substitution. The research provides a simpler and cost-effective synthesis route for these insecticides and offers insights into the structure-activity relationship for further development of effective insecticidal compounds.

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