55701-06-9

Basic information

• Product Name: (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid
• Synonyms: (1R,3R)-3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid; (1R,3R)-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid; (1R-cis)-3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid; 1R-cis-Permethric acid; cis-DCVA; cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-; Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (1R,3R)-rel-
• CAS NO: 55701-06-9
• Molecular Formula: C₈H₁₀Cl₂O₂
• Molecular Weight: 209.0698
• Mol File: 55701-06-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 290.6°C at 760 mmHg
• Flash Point: 129.6°C
• Density: 1.433g/cm³
• Vapor Pressure: 0.000512mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid(55701-06-9)
• EPA Substance Registry System: (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid(55701-06-9)

Safety Data

• Hazardous Substances Data: 55701-06-9(Hazardous Substances Data)

Usage

Description

(1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid is a cyclopropane-based compound featuring a carboxylic acid functional group. As a (1R,3R) stereoisomer, it has a distinct spatial arrangement of substituents on the first and third carbon atoms of the cyclopropane ring. The molecule is characterized by the presence of two 2,2-dichloroethenyl groups and two 2,2-dimethyl groups, which contribute to its unique chemical and physical properties. (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid may hold potential applications in various fields such as pharmaceuticals, agrochemicals, and materials science due to its distinctive structure and reactivity.

Uses

Used in Pharmaceutical Industry:
(1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique structure and reactivity make it a promising candidate for the development of new therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid is utilized as a building block for the creation of novel pesticides or herbicides. Its specific chemical properties allow for the design of targeted and effective agricultural chemicals.
Used in Materials Science:
(1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid is employed in materials science for the development of new polymers or other advanced materials. Its cyclopropane core and functional groups can be leveraged to create materials with unique properties for various applications.
Further studies and research are necessary to fully explore the potential uses and applications of (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid, as its unique structure and reactivity may lead to innovative solutions in different industries.

Upstream product

• 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 
• 59609-49-3 ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 59897-93-7 methyl trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate 
• 59042-49-8 cis-permethrinic acid 
• 309274-90-6 cis/trans-2,2-Dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid hydrazide 
• 56-23-5 tetrachloromethane 
• 7796-73-8 3,3-dimethylpent-4-enoic acid 
• 52341-32-9 permethrin 
• 61820-12-0 5-(2,2-dichlorovinyl)-4,4-dimethyl-2-oxotetrahydrofuran 
• 63406-23-5 methyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate 
• 202519-14-0 2,2,4,6,6-pentachloro-3,3-dimethylhex-5-enoic acid nitrile 
• 202519-12-8 3,3-Dichloro-5-(2,2-dichloro-vinyl)-4,4-dimethyl-dihydro-furan-2-one 

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 
• 79224-20-7 (1R,3S)-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid phenylamide 
• 60066-48-0 (1R,3S)-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid benzyl ester 
• 55701-09-2 (-)-trans-(1S,3R)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid 

Relevant articles and documents

Molecular cloning, purification, and biochemical characterization of a novel pyrethroid-hydrolyzing esterase from Klebsiella sp. strain ZD112

The gene encoding pyrethroid-hydrolyzing esterase (EstP) from Klebsiella sp. strain ZD112 was cloned into Escherichia coli and sequenced. A sequence analysis of the DNA responsible for the esfP gene revealed an open reading frame of 1914 bp encoding for a protein of 637 amino acid residues. No similarities were found by a database homology search using the nucleotide and deduced amino acid sequences of the esterases and lipases. EstP was heterologously expressed in E. coli and purified. The molecular mass of the native enzyme was approximately 73 kDa as determined by gel filtration. The results of sodium dodecyl sulfate - polyacrylamide gel electrophoresis and the deduced amino acid sequence of EstP indicated molecular masses of 73 and 73.5 kDa, respectively, suggesting that EstP is a monomer. The purified EstP not only degraded many pyrethroid pesticides and the organophosphorus insecticide malathion, but also hydrolyzed ρ-nitrophenyl esters of various fatty acids, indicating that EstP is an esterase with broad substrates. The Km for trans- and cis-permethrin and kcat/Km values indicate that EstP hydrolyzes both these substrates with higher efficiency than the carboxylesterases from resistant insects and mammals. The catalytic activity of EstP was strongly inhibited by Hg2+, Ag+, and ρ-chloromercuribenzoate, whereas a less pronounced effect (3-8% inhibition) was observed in the presence of divalent cations, the chelating agent EDTA, and phenanthroline.

Development of pyrethroid substrates for esterases associated with pyrethroid resistance in the tobacco budworm, Heliothis virescens (F.)

Assays to detect esterases associated with resistance to organophosphorus and pyrethroid insecticides in larvae of H. virescens were developed and evaluated. Cross-resistance to a variety of insecticides was measured in strains resulting from selection with either profenofos (OP-R) or cypermethrin (PYR-R), and resistance in both strains appeared to have a metabolic component. Esters were synthesized that coupled 3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate, the acid moiety of some pyrethroid insecticides, with groups (e.g., p-nitrophenyl-) that could be detected spectrophotometrically following hydrolysis of the resulting esters. Activities toward these pyrethroid esters were significantly higher in both resistant strains than those in a susceptible reference strain. In addition, all pyrethroid esters significantly increased the toxicity of cypermethrin in bioassays with larvae from both PYR-R and OP-R strains. The biological and biochemical activities of these compounds are compared with those with more conventional esterase substrates and insecticide synergists, and the utility of pyrethroid esters as components of rapid assays for detecting esterases associated with insecticide resistance is discussed.

An efficient and selective conversion of hydrazides into esters and acids

Hydrazides are selectively oxidised to esters/acids in high yields using Oxone in the presence of an appropriate alcohol/water as a nucleophile at ambient temperature. A variety of functional groups including alkenes, alcohols, ethers, cyclopropyl groups and nitriles are unaffected.