53179-78-5

Basic information

• Product Name: (1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid
• Synonyms: (1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid;1R，3R-dibromo chrysanthemic acid，1R，3R-2，2-dimethyl-3-(2，2-dibromovinyl cyclopropane carboxylic acid;Deltamethric Acid;(1R-cis)-Decamethrinic Acid;Deltamethrin Related Compound 1 (Bacisthemic Acid);(1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid
• CAS NO: 53179-78-5
• Molecular Formula: C₈H₁₀Br₂O₂
• Molecular Weight: 297.97
• Product Categories: API
• Mol File: 53179-78-5.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 326.4±32.0 °C(Predicted)
• Appearance: /
• Density: 1.993±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 3.94±0.42(Predicted)
• CAS DataBase Reference: (1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid(53179-78-5)
• EPA Substance Registry System: (1R-cis)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane carboxylic acid(53179-78-5)

Safety Data

• Hazardous Substances Data: 53179-78-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A pesticide transformation product.

Upstream product

• 108-20-3 di-isopropyl ether 
• 59898-05-4 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acid ethylester 
• 5137-55-3 Aliquat 336 
• 558-13-4 carbon tetrabromide 
• 26771-11-9 (1R)-cis-chrysanthemic acid 
• 61775-87-9 methyl <1R,cis>-2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropanecarboxylate 
• 7796-73-8 3,3-dimethylpent-4-enoic acid 
• 59042-49-8 cis-permethrinic acid 
• 111074-78-3 cis-(+)-3-(1'-acetoxy-2'-oxopropyl)-2,2-dimethyl-1-(2'-acetoxy-3'-oxo-1'-butenyl)-cycloproane 
• 111074-77-2 cis-(+)-3-(1'-acetoxy-2'-oxopropyl)-2,2-dimethyl-1-(2',3'-dioxobutyl)-cyclopropane 
• 111074-76-1 (-)-4-acetyl-2α-acetoxy-3-carene 
• 69791-70-4 cis-(-)-3-(2',2',2'-tribromomethyl-1-hydroxyethyl)-2,2-dimethyl cyclopropane-1-carboxylic acid 
• 111074-79-4 cis-(-)-3-(1-acetoxy-2-oxopropyl)-2,2-dimethyl-cyclopropane-1-carbaldehyde 
• 88669-01-6 (-)-4α-acetoxy-6,6-dimethyl-3-oxabicyclo-(3.1.0)-hex-2-one 

Downstream Products

• 200798-84-1 N-2-(1',1'-dimethylethyloxycarbonylethyl) 2,2-dimethyl-3-(2',2'-dibromoethenyl)cyclopropanecarboxyamide 
• 59952-40-8 2,2-dimethyl-3-(2',2'-dibromovinyl)-cyclopropane-1-carboxylic acid chloride 
• 55710-82-2 1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chloride 
• 53179-78-5 2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid 
• 72691-18-0 cis-(1S,3R)-Deltamethrinic acid 
• 61914-48-5 D,L-trans 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acid 
• 1141933-05-2 (-)-1-(3-phenoxyphenyl)-2-propynyl 2-(2,2-dibromoethenyl)-3,3-dimethylcyclopropanecarboxylate 
• 1141933-06-3 C₂₃H₁₉Br₂IO₃ 
• 1141933-07-4 C₂₃H₁₉Br₃O₃ 
• 1141933-08-5 C₂₃H₁₉Br₂ClO₃ 
• 1141933-09-6 C₂₄H₂₂Br₂O₃ 
• 1141933-10-9 C₂₅H₂₄Br₂O₃ 
• 1141933-11-0 C₂₅H₂₁Br₂F₃O₃ 
• 66841-58-5 2,2-dimethyl-3S-(1',2',2',2'-tetrabromo-ethyl)-cyclopropane-1R-carboxylic acid 

Relevant articles and documents

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Synthesen von (1R)-cis-3-(2',2'-Dihalovinyl)-2,2-dimethylcyclopropancarbonsaeuren via Favorskii-Umlagerung von optisch aktiven Cyclobutanonen

The cis-cyclobutanones 7 are resolved by means of optically active amine salts of their sodium hydrogen sulfite adducts.The desired (1R)-cis-carboxylic acids 9 are obtained from the (+)-cis-cyclobutanones 7 via Favorskii-rearrangement and HX-elimination.The recycling of undesired (-)-cis-cyclobutanones 7 is carried out in good yield by their racemization, thus rendering the total synthesis 1+2->9 chirally economic.

Characterization of a novel thermophilic pyrethroid-hydrolyzing carboxylesterase from Sulfolobus tokodaii into a new family

A novel gene ST2026 encoding a putative carboxylesterase from the thermophilic crenarchaeota Sulfolobus tokodaii (named EstSt7) was cloned and functionally overexpressed in Escherichia coli. The recombinant enzyme was purified to homogeneity after heat treatment, Ni-NTA affinity and Superdex-200 gel filtration chromatography. EstSt7 showed maximum activity at 80 C over 30 min and had a half-life of 180 min at 90 C. Its enzymatic activity was stable in the pH range of 8.0-10.0 with an optimum at 9.0. The enzyme exhibited significant esterase activity toward various p-nitrophenyl esters and the most preferable substrate was p-nitrophenyl butyrate (kcat/Km of 246.3 s-1 mM-1). In addition, EstSt7 showed high activity and stability against organic solvents (20% and 50% v/v) and detergents (1% and 5% v/v). Furthermore, EstSt7 could efficiently hydrolyze a wide range of synthetic pyrethroids including fenpropathrin, permethrin, cypermethrin, cyhalothrin, deltamethrin and bifenthrin, which makes it a potential candidate for the detoxification of pyrethroids for the purpose of biodegradation. Sequence alignment, phylogenetic analysis and comparison of the conserved motif reveal that this novel carboxylesterase EstSt7 should be grouped into a new bacterial lipase and esterase family.

Synthesis and biological evaluation of pyrethroid insecticide-derivatives as a chemical inducer for Bdnf mRNA expression in neurons

Brain-derived neurotrophic factor (BDNF) plays a fundamental role in neuronal synaptic plasticity. A decrease of plasticity in the brain may be related to the pathogenesis of neurodegenerative or psychiatric disorders. Pyrethroid insecticides, which affect sodium channels in neurons, are widely used to control insect pests in agriculture and in the home. We previously found that deltamethrin (DM), a type II pyrethroid, increased Bdnf mRNA expression in cultured rat cortical neurons. However, the cyano group at the α-position of type II pyrethroids is likely susceptible to hydrolytic degradation and, its degraded product, hydrogen cyanide, could generate a cellular toxicity in the human body. To determine if the cyano group is required for the Bdnf exon IV-IX (Bdnf eIV-IX) mRNA expression induced by type II pyrethroids, for this study we synthesized a series of derivatives, in which the cyano group at the α-position was replaced with an ethynyl group. Then we added various substituents at the terminal position of the ethynyl group, and biologically evaluated the effects of these derivatives on Bdnf eIV-IX mRNA expression. These ethynyl derivatives induced the Bdnf eIV-IX mRNA expression in a concentration-dependent manner, at varying levels but lower levels than that evoked by DM. The mechanisms for the Bdnf induction and the morphological changes of neurons were the same whether the cyano or ethynyl group was included in the compounds.

Diastereoselective bromination of compounds bearing a cyclohex-3-enol moiety: Application to the enantioselective synthesis of (1R)-cis-deltamethrinic acid

(Chemical Equation Presented) (1R)-cis-Chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry. Some mechanistic aspect of the addition of bromine to the C,C double bond of 2,2,5,5-tetramethylcyclohex-3-enol is disclosed.