55710-82-2

Usage

Uses

Used in Pesticide Industry:
1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chloride is used as a chloride impurity for (1R-cis)-Decamethrinic Acid, which is a pesticide transformation product. Its presence in the transformation process of the pesticide may have implications for the effectiveness and safety of the final product.
Used in Chemical Synthesis:
1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chloride can be utilized as an intermediate in the synthesis of various organic compounds. Its unique structure and functional groups make it a valuable building block for creating new molecules with specific properties and applications.
Used in Pharmaceutical Research:
Due to its chemical structure, 1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chloride may have potential applications in the development of new pharmaceuticals. Its interaction with biological targets could be explored for therapeutic purposes, such as targeting specific enzymes or receptors in the treatment of diseases.
Used in Material Science:
1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chloride's unique molecular structure may also find applications in the development of new materials with specific properties. It could be used in the creation of polymers, coatings, or other materials with tailored characteristics for various industrial applications.

Upstream product

• 53179-78-5 3-(2',2'-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid 
• 79-37-8 oxalyl dichloride 
• 53179-78-5 2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid 
• 59898-05-4 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acid ethylester 
• 52918-63-5 deltametrin 

Downstream Products

• 200798-72-7 3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid carboxy-(3-phenoxy-phenyl)-methyl ester 
• 52820-00-5 (-)-α-cyano-3-phenoxybenzyl (+)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 474457-45-9 cyano[3-(4-aminophenoxy)phenyl]methyl 1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate 
• 137115-56-1 (1R,3S)-3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid (3-cyano-2-oxo-6-phenyl-4-trifluoromethyl-2H-pyridin-1-yl)-amide 
• 1390617-14-7 C₁₈H₂₀Br₂O₄ 
• 1390617-20-5 C₁₈H₁₉Br₂ClO₄ 
• 200798-74-9 3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid (2-tert-butoxycarbonyl-ethylcarbamoyl)-(3-phenoxy-phenyl)-methyl ester 
• 200798-77-2 3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid (2-carboxy-ethylcarbamoyl)-(3-phenoxy-phenyl)-methyl ester 

Relevant academic research and scientific papers

Synthesis and characterization of chrysanthemic acid esters

A short and convenient synthesis for a series of novel chrysanthemic acid esters from aldehyde and chrysanthemic acid is reported.

Synthesis of new chiral and nonchiral pyrido [3,2-e],[1,3,4] oxadiazine derivatives

A chiral series of 6,7-dichloro-3-[3-(2,2-dihalovinyl)-2,2-dimethylcyclopropyl] -1H-pyrido [3,2-e],[1,3,4] oxadiazines (a-f) and a nonchiral series of 3-substituted, 6,7-dichloro-1H-pyrido [3,2-e][1,3,4] oxadiazines (a-g) have been synthesized. The synthesized compounds were characterized by IR, 1H-NR, HPLC and mass spectral data.

Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin

A competitive enzyme-linked immunosorbent assay (ELISA) for the detection of deltamethrin was developed. Two haptens, cyano[3-(4-aminophenoxy)phenyl]methyl 1 R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate and 3-[(±)-cyano[1R-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropan ecarbonyloxy]methyl] phenoxyacetic acid, were synthesized and conjugated with thyroglobulin as immunogens. Four antisera were generated and screened against six different coating antigens. The assay that was the most sensitive for deltamethrin was optimized and characterized. The /50 for deltamethrin was 17.5 ± 3.6 μg/L, and the lower detection limit was 1.1 ± 0.5 μg/L. This ELISA assay had relatively low cross-reactivities with other major pyrethroids, such as permethrin, phenothrin, bioresmethrin, cyfluthrin, and cypermethrin. Methanol was found to be the best organic cosolvent for this ELISA, with optimal sensitivity observed at a concentration of 40% (v/v). The assay parameters were unchanged at pH values between 5.0 and 8.0, whereas higher ionic strengths strongly suppressed the absorbances. To increase the sensitivity of the overall method, a C18 sorbent-based solid-phase extraction was used for river water samples. River water samples fortified with deltamethrin were analyzed according to this method. Good recoveries and correlation with spike levels were observed.

Hapten Synthesis for a Monoclonal Antibody Based ELISA for Deltamethrin

An enzyme-linked immunosorbent assay (ELISA) was developed for the insecticide deltamethrin. Two haptens were synthesized: the first one was a derivative of the whole molecule with a spacer arm bound to the aromatic ring; the second one was a derivative of deltamethric acid. Twelve monoclonal antibodies were obtained. A competitive ELISA using monoclonal antibody Del 01 yielded the most sensitive assay. The IC50 value for deltamethrin was estimated to be 0.5 μg mL-1 with a detection limit of 0.08,μg mL-1. Monoclonal antibody Del 01 seems to be deltamethrin specific since 1% cross-reactivity with other pyrethroid analogues was observed.

Development of Immunoassays for Type II Synthetic Pyrethroids. 1. Hapten Design and Application to Heterologous and Homologous Assays

Immunoassays differing in selectivities for pyrethroid insecticides have been developed for the detection of type II pyrethroids, including deltamethrin, cypermethrin, and λ-cyhalothrin. Two approaches were employed in hapten synthesis to raise antibodies with different cross-reactions: (1) use of three spacer attachment points to offset different parts of molecules from the points of attachment and (2) use of linkers with and without bulky groups in the enzyme conjugate to reduce antibody affinities for the spacer arm in the immunoassay. The first approach resulted in the preparation of three series of haptens with a spacer attached (1) at the aromatic moiety of pyrethroid, (2) through the middle of the molecule, and (3) at the cyclopropane moiety. Haptens based on the derivatives of the pyrethroid metabolites were also prepared. The second approach involved the use of a linker with a bulky (cyclohexane ring) functionality for preparation of an enzyme conjugate. While most combinations of antibody and conjugate could be used in immunoassays for detection of deltamethrin in the 10-100 μg/L range, in most cases the limits of detection of the assays (for total isomers of a particular target pyrethroid) were lowered 10-50 fold by treatment of the pyrethroid standards with dilute alkali to produce a different isomer mix. Fifteen antisera prepared using 8 haptens were each screened with 14 peroxidase conjugates, and 26 antibody/conjugate combinations were selected for further study on the basis of the assay sensitivity, dynamic behavior, and specificity for deltamethrin, cypermethrin, and cyhalothrin. These immunoassays provided 50% inhibition of antibody binding (IC50) values between 1.5 and 4.2 μg/L of isomerized total deltamethrin and limits of detection of 0.2-0.7 μg/L. The most sensitive immunoassay for total deltamethrin was obtained using cypermethric acid-KLH as the immunogen and a conjugate based on a derivative of cypermethrin coupled through the middle of the molecule to peroxidase. These provided an IC50 of 2 μg/L and a limit of detection of 0.2 μg/L of isomerized total deltamethrin. However, no particular hapten design produced antisera of clearly superior sensitivity or specificity for deltamethrin. Differing cross-reactions with the closely related pyrethroids, deltamethrin, cypermethrin, and cyhalothrin, were obtained, and for several antibodies the cross-reaction as well as the limits of detection could be altered by varying the conjugate combinations. Each of the 12 antibody/enzyme conjugate combinations that sensitively detected deltamethrin were very stereospecific, detecting the αS, 1R cis, (DM1), and αR, 1R cis (DM2) isomers only; the assay sensitivity was greater for the latter isomer.

(+)-4-Substituted-2-indanols

Novel compounds of the formula STR1 are disclosed in which R1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R2 is other than hydrogen are insecticides.

Process for producing (+)-4-substituted-2-indanols

Novel compounds of the formula STR1 are disclosed in which R1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R2 is other than hydrogen are insecticides.

(+)-4-Substituted-2-indanol insecticidal ester derivatives

Novel compounds of the formula STR1 are disclosed in which R1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R2 is other than hydrogen are insecticides.

Process for preparation of substituted cyclopropane carboxylic acids and esters thereof and intermediates of said acids and esters

When 1-halogeno-3-alkene-2-ol is reacted with an ortho-carboxylic ester and/or a ketene acetal, a γ-halogeno-δ-unsaturated-carboxylic ester is obtained as a main reaction product. When this intermediate is treated with a basic substance, a substituted cyclopropane-carboxylic ester is formed. This ester can be used as an insecticide or an agricultural chemical as it is or after the alcohol residue of the ester has been converted to other alcohol residue.