61898-95-1

Usage

Uses

Used in Insecticide Industry:
METHYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYL-(1-CYCLOPROPANE)CARBOXYLATE is used as an impurity in the insecticide Permethrin for its effectiveness in controlling and eliminating various insect pests. Its presence, although as an impurity, may contribute to the overall insecticidal activity of the product.
Used in Chemical Synthesis:
METHYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYL-(1-CYCLOPROPANE)CARBOXYLATE is used as a reactant in the preparation of β-ketoesters through sodium hydroxide catalyzed crossed Claisen condensation of ketene silyl acetals and methyl esters. This application highlights its utility in organic synthesis and the potential for developing new chemical compounds with various applications.

InChI:InChI=1/C9H12Cl2O2/c1-9(2)5(4-6(10)11)7(9)8(12)13-3/h4-5,7H,1-3H3/t5-,7+/m0/s1

Upstream product

• 63406-18-8 methyl 2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropane-1-carboxylate 
• 148116-22-7 1,5-Diazabicyclo[5.4.0]undec-5-ene 
• 64667-33-0 methyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate 
• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 6832-16-2 methyl diazoacetate 
• 67-56-1 methanol 
• 309274-90-6 cis/trans-2,2-Dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid hydrazide 
• 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 
• 61820-12-0 5-(2,2-dichlorovinyl)-4,4-dimethyl-2-oxotetrahydrofuran 
• 63721-05-1 methyl 3,3-dimethyl-4-penteneoate 
• 108439-48-1 1-acetoxy-5,5,5-trichloro-2E-pentene 
• 108439-51-6 methyl 5,5,5-trichloro-2E-pentanoate 
• 108439-49-2 5,5,5-trichloro-2E-penten-1-ol 

Downstream Products

• 52645-53-1 permethrin 
• 67640-14-6 (2,3,4,5,6-pentafluorophenyl)methyl 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylate 
• 55701-05-8 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 
• 55701-09-2 (-)-trans-(1S,3R)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid 
• 55667-40-8 trans-permethrin acid 
• 52341-32-9 permethrin 
• 52314-67-7 (+/-)-cis-2-(2,2-dichloroethenyl)-3,3-dimethylcyclopropanecarboxylic acid chloride 
• 52314-67-7 (+/-)-trans-2-(2,2-dichloroethenyl)-3,3-dimethylcyclopropanecarboxylic acid chloride 
• 328240-55-7 N-4-chlorobenzoyl-N'-[2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarbonyl]hydrazine 

Relevant academic research and scientific papers

Novel synthesis method for methyl dichlorochrysanthemate

The invention provides a synthesis method for methyl dichlorochrysanthemate. The process comprises the following steps: putting an amine catalyst into 3,3-dimethyl-4,6,6,6-tetrachloromethyl n-hexanoate with stirring, so as to obtain a raw material mixture; heating the obtained raw material mixture to the temperature of 20-60 DEG C, dropwise adding a liquid organic base into the raw material mixture, and enabling the mole ratio of the organic base to 3,3-dimethyl-4,6,6,6-tetrachloromethyl n-hexanoate to reach (2.0-2.5): 1; and after the dropwise adding is completed, carrying out heat preservation on the reaction mixture for 0.5-3.0 hours at the temperature of 20-60 DEG C, stopping reaction when the content of 3,3-dimethyl-4,6,6,6-tetrachloromethyl n-hexanoate is lower than 0.3%, and subjecting a product to subsequent treatment, thereby obtaining methyl dichlorochrysanthemate. According to the method provided by the invention, solvents required for the synthesis of methyl dichlorochrysanthemate are canceled, the consumption of the organic base is lowered, the reaction temperature is lowered, the reaction time is shortened, and the production of impurities such as alkyne esters is reduced while the reaction is full, so that the quality of methyl dichlorochrysanthemate is obviously improved. The method is simple in process and convenient in operation and is very beneficial to industrialization.

New catalytic system Cu(OAc)2-2,4-lutidine-ZnCl2 for olefin cyclopropanation with methyl diazoacetate

A new efficient catalytic system consisting of Cu(OAc)2, 2,4-lutidine, and ZnCl2 was found for the cyclopropanation of unsaturated compounds with methyl diazoacetate. In the case of conjugated dienes, the process occurs regioselectively at the most alkylated C=C bond.

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.

A stereoselective synthesis of methyl trans-3-(2,2-dichloroethenyl)- 2,2-dimethylcyclopropanecarboxylate

A convenient method is described for the stereoselective synthesis of methyl trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (5) via methyl 3,3-dimethyl-4,6,6,6-tetrachlorohexanoate (4) as a key intermediate, which was obtained by addition of carbon tetrachloride to methyl 3,3-dimethyl-4-pentenoate (3). Treatment of (4) with sodium methoxide in a single-vessel via methyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate (6) gave trans-rich (5) in excellent yield.

Search for Routes of Synthesis of Permethrin and Chloropermethrin Starting from Halogen-containing Alkenoic Acids

Promising procedures were developed for the synthesis of permethrin and I-chloropermethrin starting from acid chloride, nitrile, and esters of 3,3-dimethyl-2,2,4,6,6-pentachloro-5-alkenoic acid and 3,3-dimethyl-2,2,6,6-tetrachloro-5-alken-4-olide, which were prepared by adding derivatives of trichloroacetic acid to 1,1-dichloro-4-methyl-1,3-pentadiene in the presence of catalytic amounts of monovalent copper ions and amine.

Method for producing optically active cyclopropane carboxylic acid

The present relates to a process for preparing optically active cyclopropane carboxylic acid derivatives of salts thereof represented by the formula (III) STR1 wherein X is chlorine atom, bromine atom, methyl group or trifluoromethyl group and R' is hydrogen atom or metal ion, by asymmetrically hydrolyzing cyclopropane carboxylic acid esters having the formula (II) STR2 wherein X is as defined above and R is C1-4 alkyl group or halogen-substituted C1-4 alkyl group with specific strains of microorganisms or esterase derived therefrom.

Process for production of β-dihalogenoethenylcyclopropane derivatives

A novel process for producing a β-dihalogenoethenylcyclopropane derivative of the formula, STR1 wherein R1 is a hydrogen atom or an alkyl group, R3 is a hydrogen atom, lower alkyl, acyl, carboxyl or alkoxycarbonyl group and R is a hydrogen atom or a lower alkyl group and each of Y1 and Y2 is a fluorine, chlorine or bromine atom respectively, which is an acidic moiety of the useful synthetic insecticides of the pyrethrin type, which process comprises a combination of a series of sequential steps starting from alkyl 3-butenyl ketone derivative of the formula (I), which may be shown according to the following reaction scheme: STR2 According to this process, objective compound of the formula (VI) having any cis/trans ratio can be produced by selecting the reaction condition of the Stages II-1, II-2, and IV-2.

Process for the preparation of vinylcyclopropanecarboxylic acid derivatives

Disclosed is a process for preparing cis-trans isomer mixtures of 2,2-dimethyl-3(β,β-dichlorovinyl)-cyclopropane-1-carboxylic acid esters, having a high cis/trans isomer ratio, wherein a 4,4-dimethyl-5-halogen-6-alkoxytetrahydro-pyrone or a 3,3-dimethyl-4-halogen-5-oxo-pentanic acid ester is reacted with dichlorophosphonic acid esters in the presence of alkali alcoholates or alkali hydrides or lithium alkyls. Also disclosed are novel starting tetrahydropyrone compounds usable in the above process, and a process for preparation of the novel compounds which includes reacting β,β-dimethyl-γ,δ-dihalogen-δ-valerolactones with alkali alcoholates at reaction temperatures between -10° and +50° C.