alpha-Cypermethrin

Base Information

• Chemical Name: alpha-Cypermethrin
• CAS No.: 65731-84-2
• Deprecated CAS: 70982-02-4
• Molecular Formula: C22H19Cl2NO3
• Molecular Weight: 416.304
• European Community (EC) Number: 276-458-2,265-898-0,614-054-3
• UNII: 2TF5M1O25X,99W8X078CA
• DSSTox Substance ID: DTXSID80274146
• Nikkaji Number: J307.470F
• Wikidata: Q27119819
• NCI Thesaurus Code: C77378
• Metabolomics Workbench ID: 56242
• Mol file: 65731-84-2.mol

Synonyms:alpha-cypermethrin;alphacypermethrin;alphamethrin;beta-cipermetrina;Cymbush;cypermethrin;cypermethrin, (1alpha(S*),3alpha)-(+-)-isomer;cypermethrin, (1R-(1alpha(R*),3beta))-isomer;cypermethrin, (1R-(1alpha(S*),3beta))-isomer;Fastac 50EC;Fendona;NRDC 149;supercypermethrin;supermethrin;WL 85871;WL-85871

Chemical Property of alpha-Cypermethrin

Chemical Property:

• Vapor Pressure: 2.03E-27mmHg at 25°C
• Melting Point: 60-80oC
• Boiling Point: 511.3 °C at 760 mmHg
• Flash Point: 263 °C
• PSA: 59.32000
• Density: 1.329 g/cm³
• LogP: 6.17798
• Water Solubility.: 0.09 mg l-1(25 °C)
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 415.0741989
• Heavy Atom Count: 28
• Complexity: 643

Purity/Quality:

99% ^*data from raw suppliers

(1R,2R,1''S)-Cypermethrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Pyrethrins/Pyrethroids
• Canonical SMILES: CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
• Isomeric SMILES: CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
• Uses: Beta-cypermethrin is used to control a wide range of insects, especially Lepidoptera and Coleoptera, in alfalfa, cotton, cereals, fruit, vines, vegetables, beans, beets, tobacco, oilseed rape and other crops. It is also used for insect control in public health and for ectoparasite control on animals. (1R,2R,1''S)-Cypermethrin functions as a degartion product (Pyrethroid insecticides) used in agriculture. Insecticidal activity of most active isomers of fenvalerate and other recent pyrethroids.

Technology Process of alpha-Cypermethrin

There total 22 articles about alpha-Cypermethrin 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: 82.0%

(1R,3R)-(+)-3-(2,2-Dichlorvinyl)-2,2-dimethylcyclopropanecarboxylic acid chloride (69831-14-7) + (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4,52315-06-7,61826-76-4,71962-66-8) → (+)-(S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate (65731-84-2)

Guidance literature:

With pyridine; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1016/S0957-4166(98)00047-0

Reference yield:

cypermethrine (52315-07-8) → [(S)-cyano-(3-phenoxyphenyl)methyl](1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate (488113-10-6) + (R)-α-cyano-3-phenoxybenzyl (1R,3R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (66841-24-5) + (+)-(S)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate (65731-84-2) + (R)-α-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2,2-dimethyl-cycloprpanecarboxylate

Guidance literature:

Resolution of stereoisomers;

DOI:10.1021/jf900921g

Reference yield:

→ Alpha-cypermethrin (52315-07-8,65731-83-1,65731-84-2,65732-07-2,66290-20-8,66290-21-9,66841-24-5,67375-30-8,70982-01-3,70982-02-4,71697-59-1,72204-43-4,72204-44-5,83860-31-5,83860-32-6,137430-99-0,137432-55-4)

Guidance literature:

entspr.Saeurechlorid, entspr.Alkohol;

upstream raw materials:

(1R,3R)-(+)-3-(2,2-Dichlorvinyl)-2,2-dimethylcyclopropanecarboxylic acid chloride

(S)-m-phenoxybenzaldehyde cyanohydrin

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

alpha-cyano-3-phenoxybenzyl acetate

Downstream raw materials:

4-{[2-[3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarbonyloxy]-2-(3-phenoxy-phenyl)-acetylamino]-methyl}-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester

4-{[2-[3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarbonyloxy]-2-(3-phenoxy-phenyl)-acetylamino]-methyl}-cyclohexanecarboxylic acid

3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid (2-tert-butoxycarbonyl-ethylcarbamoyl)-(3-phenoxy-phenyl)-methyl ester

3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid (2-tert-butoxycarbonyl-ethylcarbamoyl)-(3-phenoxy-phenyl)-methyl ester

Refernces

• 1、 Nillos, Mae Grace,Qin, Sujie,Larive, Cynthia,Schlenk, Daniel,Gan, Jay. "Epimerization of cypermethrin stereoisomers in alcohols". experimental part. p. 6938 - 6943. Retrieved 2010/07/15.
• 2、 Roos, Juergen,Stelzer, Uwe,Effenberger, Franz. "Synthesis of (1R,cis,αS)-cypermethrine via lipase catalyzed kinetic resolution of racemic m-phenoxybenzaldehyde cyanohydrin acetate". . p. 1043 - 1049. Retrieved 2007/10/03.