Permethrin

Base Information

• Chemical Name: Permethrin
• CAS No.: 52645-53-1
• Deprecated CAS: 57608-04-5,60018-94-2,63364-00-1,75497-64-2,93388-66-0,60018-94-2,63364-00-1,75497-64-2,93388-66-0
• Molecular Formula: C21H20Cl2O3
• Molecular Weight: 391.294
• Hs Code.: 29162090
• European Community (EC) Number: 258-067-9
• ICSC Number: 0312
• NSC Number: 760105
• UN Number: 3077,3352,2588
• DSSTox Substance ID: DTXSID8022292
• Nikkaji Number: J10.127C
• Wikipedia: Permethrin
• Wikidata: Q411635
• NCI Thesaurus Code: C29354
• RXCUI: 33199
• Metabolomics Workbench ID: 123595
• ChEMBL ID: CHEMBL1525
• Mol file: 52645-53-1.mol

Synonyms:(m-Phenoxybenzyl)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate;3-Phenoxybenzyl-(+-)-cis,trans-2,2-dichlorovinyl-2,2-dimethyl-cyclopropylcarboxylic acid, ester;3-Phenoxybenzyl-cis,trans-(1RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate;Ambush;cis permethrin;cis-(1RS)-permethrin;cis-permethrin;Cyclopropanecarboxylic Acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester;Elimite;FMC 33297;FMC-33297;FMC33297;NIA 33297;NIA-33297;NIA33297;Nittifor;NRDC 143;NRDC 147;NRDC-143;NRDC-147;NRDC143;NRDC147;Permethrin;Permethrin, (1R-cis)-Isomer;Permethrin, (1R-trans)-Isomer;Permethrin, (1S-cis)-Isomer;Permethrin, (1S-trans)-Isomer;Permethrin, (cis)-Isomer;Permethrin, (cis-(+-))-Isomer;Permethrin, (trans)-Isomer;Permethrin, (trans-(+-))-Isomer;permethrin, cis-(1RS)-isomer;Permethrin, trans-(1RS)-Isomer;PP 557;PP-557;PP557;S 3151;S-3151;S3151;trans permethrin;trans-(1RS)-Permethrin;trans-permethrin

Chemical Property of Permethrin

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Vapor Pressure: 4.58E-11mmHg at 25°C
• Melting Point: 34-35 °C
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 465.9 °C at 760 mmHg
• Flash Point: 159.4 °C
• PSA: 35.53000
• Density: 1.293 g/cm³
• LogP: 6.11330
• Storage Temp.: 0-6°C
• Water Solubility.: insoluble
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 390.0789499
• Heavy Atom Count: 26
• Complexity: 521
• Transport DOT Label: Class 9

Purity/Quality:

95%TC, ^*data from raw suppliers

Permethrin(cis/transmixture) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N, T, F
• Hazard Codes: Xn,N,T,F
• Statements: 20/22-43-50/53-39/23/24/25-23/24/25-11-51/53-36-20/21/22
• Safety Statements: 13-24-36/37/39-60-61-45-36/37-16-7-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Pyrethrins/Pyrethroids
• Canonical SMILES: CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
• Recent ClinicalTrials: Comparison of Topical 5% Permethrin and Topical 10% Sulfur in the Treatment of Scabies
• Recent EU Clinical Trials: Investigation to assess the efficacy of topical benzyl benzoate 10/25% emulsion versus permethrin 5% creme for scabies treatment
• 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.
• Description: Yellow-brown to brown liquid, which sometimes tends to crystallize at room temperature (technical grade). Permethrin, a pyrethroid insecticide with little mammalian toxicity, has been marketed as a tick repellent. Permethrin is the only synthetic pyrethroid that is used worldwide for head lice. The spray formulation is the most widely available form. Once applied to clothing, it is stable through several wash cycles. It is also suitable for treating sleeping bags, tents, and fabric used for insect screening. A liquid concentrate has been used to impregnate fabric for as long as the life of the garment. Permethrin is particularly helpful in the prevention of tick and chigger bites. These crawling arthropods must travel across the treated fabric, whereas flying insects tend to be attracted directly to exposed skin. The combination of a DEET-containing repellent and permethrin-treated clothing is generally highly ffective against a wide range of biting arthropods.
• Uses: Permethrin is a synthetic pyrethroid active against lice, ticks, mites, and fleas. It acts on neural cellmembranes, delaying repolarization and causing paralysis. The compound has no reported adverse properties, is heat and light stable, has 70% to 80% ovicidal activity, and leaves an active residue on the scalp. Permethrin is 26 times less toxic than lindane and 3 times less toxic than pyrethrins. A 1% permethrin cream rinse (Nix) preparation with a single application was determined to be more effective than treatment with RID. Permethrin-treated military uniforms are effective against human body lice. Apply the cream rinse for 10 minutes and rinse off with water. Localized pruritus may be reported with use of this product. Labelled Permethrin (P288500). Synthetic pyrethroid insectide, more stable to light and at least as active as the natural pyrethrins and with low mammalian toxicity. For the treatment of infestation with Sarcoptes scabiei (scabies); antihyperlipidemic; cholesterol sequestrant.
• Indications: Permethrin is a synthetic pyrethroid active against lice, ticks, mites, and fleas. It acts on neural cellmembranes, delaying repolarization and causing paralysis. The compound has no reported adverse properties, is heat and light stable, has 70% to 80% ovicidal activity, and leaves an active residue on the scalp. Permethrin 0.5% spray kills ticks and repels mosquitoes and stable flies. It is broken down when applied to skin and, hence, should be applied to clothing, shoes, tents, and so on. Spray only enough to moisten the material. Spray on clothing at least 2 hours before wearing. One treatment should last through a few washings.
• Clinical Use: Permethrin is 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylicacid (3-phenoxyphenyl)methylester or 3-(phenoxyphenyl)methyl (±)-cis, trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate(Nix). This synthetic pyrethrinoid compound is more stablechemically than most natural pyrethrins and is at least as activeas an insecticide. Of the four isomers present, the1(R),trans and 1(R),cis-isomers are primarily responsiblefor the insecticidal activity. The commercial product is amixture consisting of 60% trans and 40% cis racemic isomers.It occurs as colorless to pale yellow low-melting crystalsor as a pale yellow liquid and is insoluble in water butsoluble in most organic solvents.Permethrin exerts a lethal action against lice, ticks, mites,and fleas. It acts on the nerve cell membranes of the parasitesto disrupt sodium channel conductance. It is used as apediculicide for the treatment of head lice. A single applicationof a 1% solution effects cures in more than 99% ofcases. The most frequent side effect is pruritus, which occurredin about 6% of the patients tested.

Technology Process of Permethrin

There total 24 articles about Permethrin 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: 100.0%

2,2-Dimethyl-3-(2,2,2-trichloro-ethyl)-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester → permethrin (52645-53-1,93388-66-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; Heating;

DOI:10.1246/cl.1994.703

Reference yield: 95.0%

tetra-n-butylphosphonium chloride (2304-30-5) + 3-Phenoxybenzyl alcohol (13826-35-2) + 4-(2,2-dichloroethenyl)dihydro-5,5-dimethyl-2(3H)-furanone (63142-59-6) → permethrin (52645-53-1,93388-66-0)

Guidance literature:

With potassium hydroxide; thionyl chloride; In ice-water; toluene; benzene;

Reference yield: 94.0%

cis,trans methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate (61898-95-1) + 3-Phenoxybenzyl alcohol (13826-35-2) → (3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-chloroethynyl)cyclopropanecarboxylate + permethrin (52645-53-1,93388-66-0)

Guidance literature:

With lithium methanolate; In methanol; xylene; at 100 - 145 ℃; for 12h; Heating / reflux;

upstream raw materials:

3-phenoxybenzyl bromide

cis-permethrinic acid

1,1-dichloro-4-methyl-penta-1,3-diene

methyl 2,2-dimethyl-3-(2,2-dichloroethenyl)cyclopropane-1-carboxylate

Downstream raw materials:

cis-permethrinic acid

3-Phenoxybenzyl alcohol

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

(1R,3S)-3-Chloroethynyl-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester

Refernces

• 1、 Nakatsuji, Hidefumi,Morimoto, Mami,Misaki, Tomonori,Tanabe, Yoo. "Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively". . p. 12071 - 12080. Retrieved 2008/03/13.
• 2、 -. "Method for producing cyclopropanecarboxylates". . . Retrieved 2008/06/13.