55701-05-8

Basic information

• Product Name: Permethric acid
• Synonyms: 3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropanecarboxylicaci;3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylicacid;trans-dcva;Permethric acid;3-(2,2-Dichloroethenyl)-2,2-dimethyl-cyclopropanecarboxylate;Permethrinic acid;3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid;dichloro chrysanthemic acid，(±)cis，trans-2，2-dimethyl-3-(2，2-dichloro vinyl cyclopropane carboxylic acid)
• CAS NO: 55701-05-8
• Molecular Formula: C₈H₁₀Cl₂O₂
• Molecular Weight: 209.07
• EINECS: 259-768-2
• Mol File: 55701-05-8.mol
• Article Data: 54

Chemical Properties

• Melting Point: 58.33 °C
• Boiling Point: 290.6 ºC at 760 mmHg
• Flash Point: 129.6 ºC
• Appearance: /
• Density: 1.433 g/cm3
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 4.09±0.33(Predicted)
• CAS DataBase Reference: Permethric acid(CAS DataBase Reference)
• NIST Chemistry Reference: Permethric acid(55701-05-8)
• EPA Substance Registry System: Permethric acid(55701-05-8)

Safety Data

• Hazardous Substances Data: 55701-05-8(Hazardous Substances Data)

Usage

Uses

3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic Acid is a reagent used in the preparation of hapten and immunogen for the production of polyclonal antibodies, specific to Cypermethrin (C989000).

InChI:InChI=1/C8H10Cl2O2/c1-8(2)4(3-5(9)10)6(8)7(11)12/h3-4,6H,1-2H3,(H,11,12)

Upstream product

• 68359-37-5 cyfluthrin 
• 59897-93-7 methyl trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate 
• 59609-49-3 ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 61898-95-1 cis,trans methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 42125-67-7 trivinyl orthoacetate 
• 556-82-1 3-methyl-2-buten-1-ol 
• 52645-53-1 permethrin 
• 61820-11-9 1-cyano-3-(2',2'-dichlorovinyl)-2,2-dimethylcyclopropane 
• 59897-92-6 ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate 
• 52314-67-7 permethric acid chloride 
• 31896-10-3 N-(2,2,2-trichloro-1-piperazin-1-yl-ethyl)-formamide 
• 1310-58-3 potassium hydroxide 

Downstream Products

• 52341-32-9 permethrin 
• 55701-08-1 (-)-cis-(1S,3S)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclopropanecarboxylic acid 
• 55701-03-6 (+)-trans-(1R,3S)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid 
• 55667-40-8 1(R)-cis-permethrinic acid 
• 55701-09-2 (-)-trans-(1S,3R)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid 
• 59609-49-3 ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 52314-67-7 permethric acid chloride 
• 52315-07-8 cypermethrine 
• 74569-26-9 α-fluoro-3-phenoxybenzyl 2,2-dimethyl-3-(β,β-dichlorovinyl)cyclopropane-1-carboxylate 
• 67328-58-9 4-OH-c,t-permethrin 
• 61949-76-6 3-phenoxybenzyl (1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 93388-66-0 3-phenoxybenzyl (1RS)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 1293376-79-0 3-(2,2-dichlorovinyl)-2,2-dimethyl-N-[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide 
• 1293376-88-1 3-(2,2-dichlorovinyl)-2,2-dimethyl-N-[5-(3-fluorophenyl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide 

Relevant articles and documents

Biodegradation of β-Cyfluthrin by Fungi

Five fungal species, namely, Trichoderma viride strain 5-2, T. viride strain 2211, Aspergillus niger, A. terricola, and Phanerochaete chrysoporium were screened for degradation study of β-cyfluthrin. Each fungal species was allowed to grow in Czapek dox medium containing β-cyfluthrin (5 mg/mL) as the major carbon source of the medium. The highest degradation of β-cyfluthrin was observed by T. viride 5-2 (T1/2 = 7.07 days), followed by T. viride 2211 (T1/2 = 10.66 days). The degradation of β-cyfluthrin followed first-order kinetics with a fast degradation rate during first 7 days of growth of the fungi. In the case of T. viride strain 5-2, five degradation products were isolated after 20 days of growth of the fungi, out of which three products were identified as α -cyano-4-fluorobenzyl-3-(2,2-dichlorovinyl)-2,2-dimethyl cyclopropane carboxylate, α-cyano-4-fluoro-3-phenoxy benzyl alcohol, and 3(2,2-dichlorovinyl)-2,2-dimethyl cyclopropanoic acid.

Synthesis method of DV-chrysanthemic acid

The invention provides a synthesis method of DV-chrysanthemic acid. The synthesis method comprises the steps of firstly, heating isopentenol and ethyltrivinyl under an acidic condition to synthesize an intermediate dimethyl-pentenoic acid ethyl ester; secondly, adding carbon tetrachloride, isopropanol and aluminum trichloride, mixing, and cooling for reaction to obtain methyl dichlorochrysanthemate; and finally, hydrolyzing and distilling under reduced pressure to remove the organic solvent to obtain the product 3-(2,2-dichloroethyenyl)-2,2-dimethylcyclopropanecarboxylic acid. The product 3-(2,2-dichloroethyenyl)-2,2-dimethylcyclopropanecarboxylic acid is obtained through a three-step reaction, and the preparation method has the advantages of small side reaction, safety, environmental protection, suitableness for large-batch industrial production, and wide application prospect.

Stereoselective biotransformation of permethrin to estrogenic metabolites in fish

This study investigated the stereoselective biotransformation and resulting estrogenic activity of the pyrethroid insecticide, permethrin (PM). Results of both in vivo (male Japanese medaka, vitellogenin (VTG) protein in plasma) and in vitro (primary rainbow trout hepatocyte VTG-mRNA expression) assays indicated stereoselective estrogenic activity of PM. 1S-cis-PM was observed to have significantly higher activity (P ≤ 0.05) than the 1R-cis enantiomer in both in vivo and in vitro evaluations. All enantiomers of PM were oxidized to a 4′-hydoxy PM (4OH PM) metabolite and underwent esterase cleavage to 3-phenoxybenzyl alcohol (3-PBOH) and 3-(4′-hydroxyphenoxy)-benzyl alcohol) (3,4′-PBOH). Racemic 4OH PM as well as 3-PBOH, and 3,4′-PBOH possessed significant (P ≤ 0.05) estrogenicity. 1S-trans-PM underwent esterase cleavage more extensively than the corresponding 1R-trans-PM. Inhibition studies with ketoconazole confirmed cytochrome P450-catalyzed hydroxylation as well as esterase cleavage of PM for all stereoisomers. These studies indicated stereoselectivity in the estrogenic activity of PM resulting from stereoselective biotransformation of the parent compound to more estrogenic metabolites.