cis-Permethrin

Base Information

• Chemical Name: cis-Permethrin
• CAS No.: 52341-33-0
• Molecular Formula: C₂₁H₂₀Cl₂O₃
• Molecular Weight: 391.294
• European Community (EC) Number: 263-346-3
• UNII: 620Q217008,GC30YV53C8
• DSSTox Substance ID: DTXSID0038338,DTXSID5052208
• Nikkaji Number: J85.254F
• Metabolomics Workbench ID: 144188
• ChEMBL ID: CHEMBL589356
• Mol file: 52341-33-0.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 cis-Permethrin

Chemical Property:

• Refractive Index: 1.6500 (estimate)
• Boiling Point: 505.74°C (rough estimate)
• PSA: 71.06000
• Density: 1.1531 (rough estimate)
• LogP: 12.22660
• 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

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
• Isomeric SMILES: CC1([C@H]([C@H]1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

Technology Process of cis-Permethrin

There total 9 articles about cis-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:

3-phenoxybenzyl bromide (51632-16-7) + cis-permethrinic acid (59042-49-8) → (1RS)-cis-permethrin (51877-74-8,52341-32-9,52341-33-0,54774-45-7,54774-46-8,54774-47-9,61949-76-6,61949-77-7,52645-53-1,93388-66-0)

Guidance literature:

With triethylamine; In acetone; at 35 ℃; for 3h;

Reference yield:

1,1-dichloro-4-methyl-penta-1,3-diene (55667-43-1) → (1RS)-cis-permethrin (51877-74-8,52341-32-9,52341-33-0,54774-45-7,54774-46-8,54774-47-9,61949-76-6,61949-77-7,52645-53-1,93388-66-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 20 percent / Cu₂O, CuCl, dibutylamine / 1 h / 100 - 110 °C

2: 87 percent / Zn/Cu / methanol

3: 80 percent / HCl / 4 h / Ambient temperature

4: NaOMe / methanol / 2 h / 50 °C

5: 95 percent / NaOH / methanol / 8 h / 40 °C

6: 3.52 g / Et₃N / acetone / 3 h / 35 °C

With copper(I) oxide; hydrogenchloride; sodium hydroxide; sodium methylate; copper; dibutylamine; triethylamine; copper(l) chloride; zinc; In methanol; acetone;

Reference yield:

methyl 2,2-dimethyl-3-(2,2-dichloroethenyl)cyclopropane-1-carboxylate (61976-30-5) → (1RS)-cis-permethrin (51877-74-8,52341-32-9,52341-33-0,54774-45-7,54774-46-8,54774-47-9,61949-76-6,61949-77-7,52645-53-1,93388-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / NaOH / methanol / 8 h / 40 °C

2: 3.52 g / Et₃N / acetone / 3 h / 35 °C

With sodium hydroxide; triethylamine; In methanol; acetone;

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

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

Refernces