63935-26-2

Basic information

• Product Name: 2，2-dichloro-1-(4-ethyoxy phenyl)cy-clopropane carboxylic acid
• Synonyms: 2，2-dichloro-1-(4-ethyoxy phenyl)cy-clopropane carboxylic acid
• CAS NO: 63935-26-2
• Molecular Weight: 0
• Mol File: 63935-26-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2，2-dichloro-1-(4-ethyoxy phenyl)cy-clopropane carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2，2-dichloro-1-(4-ethyoxy phenyl)cy-clopropane carboxylic acid(63935-26-2)
• EPA Substance Registry System: 2，2-dichloro-1-(4-ethyoxy phenyl)cy-clopropane carboxylic acid(63935-26-2)

Safety Data

• Hazardous Substances Data: 63935-26-2(Hazardous Substances Data)

Usage

General Description

2，2-dichloro-1-(4-ethyoxy phenyl)cy-clopropane carboxylic acid is a chemical compound with the molecular formula C13H15Cl2O3. It is commonly known as Etofenprox and is used as an insecticide in various commercial and agricultural applications. Etofenprox acts as a neurotoxin to target insects, disrupting their nervous systems and causing paralysis and eventual death. It is effective against a wide range of pests, including mosquitoes, ants, cockroaches, and flies. Etofenprox is considered to have low toxicity to mammals and other non-target organisms, making it a valuable option for pest control while minimizing environmental impact.

Upstream product

• 91852-63-0 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid chloride 
• 104023-75-8 1-(4'-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid 
• 84772-63-4 (R)-2,2-Dichloro-1-(4-ethoxy-phenyl)-cyclopropanecarboxylic acid (3aR,4R,6aR)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 84772-64-5 (S)-2,2-Dichloro-1-(4-ethoxy-phenyl)-cyclopropanecarboxylic acid (3aR,4R,6aR)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 103-73-1 Phenetole 
• 888498-57-5 methyl 2-(4-ethoxyphenyl)lactate 
• 928118-57-4 2-(4-ethoxy-phenyl)-acrylic acid methyl ester 
• 101492-41-5 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid methyl ester 

Downstream Products

• 1162060-61-8 2,2-dichloro-1-(4-ethoxyphenyl)-N-(4-nitrophenyl)-cyclopropane carboxamide 

Relevant articles and documents

Practical, general, and systematic method for optical resolution of gem-dihalo- and monohalocyclopropanecarboxylic acids utilizing chiral 1,1′-binaphtholmonomethyl ethers: Application to the synthesis of three chiral pesticides

We performed an efficient practical and systematic optical resolution method for gem-dihalo- and monohalocyclopropanecarboxylic acids 1 and 5 utilizing chiral 1,1′-binaphthol monomethyl ether (R)-2 as the key auxiliary. Direct esterification of 1 with (R)-2 gave two 1R- and 1S-diastereomeric esters 3 with marked different Rf values, both of which were easily separated using simple column chromatography. Monodehalogenation of separated chiral esters 3 using t-BuMgCl and cat. Co(dppe)2Cl2 gave two 1,2-trans- and 1,2-cis-diastereomers 4 with markedly different Rf values, both of which were similarly separated using simple column chromatography. The obtained diastereomers 3 and 4 were easily hydrolyzed to the desired enantiopure acids 1 (>99%) and 5 (>99%), respectively, with recovery of (R)-2, both in good to excellent yields. Utilizing the present method, important chiral agrochemicals, carpropamid 6 and fencyclate 7, were readily synthesized. Pyrethroid 9 with three asymmetric centers was efficiently synthesized in a much better yield compared with the reported method. The Royal Society of Chemistry 2008.

Investigation of Readily Available Chiral Compounds for Preparative Scale Resolutions

Diastereoisomeric esters were formed by reaction of racemic carboxylic acids with the readily available hydroxy lactone derivatives, 2,3-O-isopropylidene-D(+)-ribono-1,4-lactone, D(-)-2-hydroxy-3,3-dimethylbutyro-1,4-lactone (D(-)-pantolactone) and 1,2-O-isopropylidene-(+)-a-D-glucofuranurono-6,3-lactone.In all cases separation of the diastereoisomeric esters was achieved by crystallization and/or chromatography.Purity of the diastereoisomers could be determined by h.p.l.c. or by 1H n.m.r.Hydrolysis under mild basic conditions followed by treatment with acid gave optically pure carboxylic acids.The facile separation by crystallization and/or chromatography of diastereoisomers prepared from racemic endo-1,4,5,6,7,7-hexachlorobicyclohept-5-ene-2-carboxylic acid suggested that the resolved acid may be useful as a resolving agent.This was shown by separation of diastereoisomers formed from the resolved acid and racemic 1-(3'-phenoxyphenyl)prop-2-yn-1-ol and racemic 1-cyano-1-(3'-phenoxyphenyl)methanol respectively.Optically pure 1-(3'-phenoxyphenyl)prop-2-yn-1-ol was obtained by hydrolysis of the separated diastereoisomers.

Insecticidal esters

The (+), (-) and (±) forms of the compounds of formula I STR1 wherein R1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, and R2 is a hydrogen o