55701-08-1

Basic information

• Product Name: Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1S,3S)-
• Synonyms: 1S-cis-permethric acid;[1S,-cis]-2,2-dimethyl-3-(2,2-dichlorovinyl) cyclopropane carboxylic acid;(1S,3S)-PERMETHRIC ACID;2,2-Dimethyl-3-cis-(β,β-dichlorvinyl)-cyclopropancarbonsaeure;(1R)-cis-permethrinic acid;(1S,3S)-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid;2,2-Dimethyl-3-(2,2-dichlorvinyl)cyclopropancarbonsaeure;(1S)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid
• CAS NO: 55701-08-1
• Molecular Formula: C8H10Cl2O2
• Molecular Weight: 209.072
• Mol File: 55701-08-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 290.6±30.0 °C(Predicted)
• Density: 1.433±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1S,3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1S,3S)-(55701-08-1)
• EPA Substance Registry System: Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1S,3S)-(55701-08-1)

Safety Data

• Hazardous Substances Data: 55701-08-1(Hazardous Substances Data)

Upstream product

• 55701-05-8 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 
• 63142-56-3 ethyl (+/-)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 61898-95-1 cis,trans methyl 2,2-dimethyl-3-(2',2'-dichlorovinyl)-cyclopropanecarboxylate 
• 59897-93-7 methyl trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate 
• 56-23-5 tetrachloromethane 
• 7796-73-8 3,3-dimethylpent-4-enoic acid 
• 63170-40-1 1,1,1-trichloro-2-acetoxy-4-methyl-3-pentene 
• 72800-48-7 1,1,1-trichloro-4-methyl-3-penten-2-ol 
• 72183-62-1 4-(2',2',2'-Trichloraethyl)-2-hydroxy-3,3-dimethylcyclobutanon 
• 202519-12-8 3,3-Dichloro-5-(2,2-dichloro-vinyl)-4,4-dimethyl-dihydro-furan-2-one 
• 202519-14-0 2,2,4,6,6-pentachloro-3,3-dimethylhex-5-enoic acid nitrile 
• 63406-23-5 methyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate 

Downstream Products

• 52315-02-3 3t-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropane-r-carboxylic acid-(3-allyl-2-methyl-4-oxo-cyclopent-2-enyl ester) 
• 55701-03-6 (+)-trans-(1R,3S)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid 
• 52314-67-7 (+/-)-trans-2-(2,2-dichloroethenyl)-3,3-dimethylcyclopropanecarboxylic acid chloride 
• 52341-32-9 permethrin 
• 55701-09-2 (-)-trans-(1S,3R)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid 
• 569679-06-7 3-(tert-butyl) 2-methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate 
• 60066-48-0 (1R,3S)-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid benzyl ester 
• 79224-20-7 (1R,3S)-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid phenylamide 

Relevant articles and documents

A diastereoselective synthesis of boceprevir's gem-dimethyl bicyclic [3.1.0] proline intermediate from an insecticide ingredient cis-cypermethric acid

An efficient multi-gram synthesis of (1R,2S,5S)-methyl 6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate, a key chiral bicyclic proline fragment employed in the construction of the potent anti-HCV drug boceprevir, has been presented. The synthetic route commences with the readily available cis-cypermethric acid, a cheap source of the cyclopropane ring required in the targeted compound, and utilizes the cis-orientation of the 2,2-dichlorovinyl and carboxylic acid side arms, already present in the starting material, to effect a diastereoselective construction of the proline moiety.

Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11

The pyrethroid pesticides residues on foods and environmental contamination are a public safety concern. Pretreatment with pyrethroid hydrolase has the potential to alleviate the conditions. For this purpose, a fungus capable of using pyrethroid pesticides as a sole carbon source was isolated from the soil and characterized as Aspergillus niger ZD11. A novel pyrethroid hydrolase from cell extract was purified 41.5-fold to apparent homogeneity with 12.6% overall recovery. It is a monomeric structure with a molecular mass of 56 kDa, a pl of 5.4, and the enzyme activity was optimal at 45°C and pH 6.5. The activities were strongly inhibited by Hg2+, Ag+, and p-chloromercuribenzoate, whereas less pronounced effects (5-10% inhibition) were observed in the presence of the remaining divalent cations, the chelating agent EDTA and phenanthroline. The purified enzyme hydrolyzed various insecticides with similar carboxylester. trans-Permethrin is the preferred substrate.

Free radical addition of haloalkanes to polymer bound olefins and its application to the solid-phase synthesis of pyrethroids

Polymer bound olefins undergo free radical initiated 1,2-addition when reacted with a variety of haloalkanes. The strategy could be applied successfully to the solid-phase synthesis of dihaloethenylcyclopropane carboxylic acids which are the key fragments of synthetic pyrethroids.