61898-95-1

Basic information

• Product Name: METHYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYL-(1-CYCLOPROPANE)CARBOXYLATE
• Synonyms: Cyclopropanecarboxylicacid,3-(2,2-dichloroethenyl)-2,2-dimethyl-,methylester;Methyl 3-(2,2-dichloroethenyl)-2,2-diMethylcyclopropanecarboxylate;Permethrin EP Impurity B (DCVC Methyl Ester) (Mixture of Diastereomers);3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid methyl ester;3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid methyl ester;Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-,methyl e;methyl 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylate;Methyl3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
• CAS NO: 61898-95-1
• Molecular Formula: C₉H₁₂Cl₂O₂
• Molecular Weight: 223.1
• EINECS: 263-308-6
• Mol File: 61898-95-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 234-235 °C
• Flash Point: 88.1 °C
• Appearance: /
• Density: 1.304
• Vapor Pressure: 0.0412mmHg at 25°C
• Refractive Index: 1.492-1.5
• CAS DataBase Reference: METHYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYL-(1-CYCLOPROPANE)CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYL-(1-CYCLOPROPANE)CARBOXYLATE(61898-95-1)
• EPA Substance Registry System: METHYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYL-(1-CYCLOPROPANE)CARBOXYLATE(61898-95-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36
• Hazardous Substances Data: 61898-95-1(Hazardous Substances Data)

Usage

Description

METHYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYL-(1-CYCLOPROPANE)CARBOXYLATE, also known as Permethrinic Acid Methyl Ester, is an impurity found in the synthetic pyrethroid insecticide Permethrin. It is characterized by its dichloro vinyl and dimethyl cyclopropane carboxylate functional groups, which contribute to its chemical properties and potential applications.

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

• 67-56-1 methanol 
• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 6832-16-2 methyl diazoacetate 
• 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 
• 64667-33-0 methyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate 
• 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 
• 41905-26-4 trans-1,1,1,5-tetrachloro-3-pentene 
• 108439-50-5 5,5,5-trichloro-2E-pentenoic acid 
• 309274-90-6 cis/trans-2,2-Dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid hydrazide 

Downstream Products

• 52341-32-9 permethrin 
• 55667-40-8 trans-permethrin acid 
• 55701-09-2 (-)-trans-(1S,3R)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid 
• 55701-05-8 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 
• 67640-14-6 (2,3,4,5,6-pentafluorophenyl)methyl 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylate 
• 52645-53-1 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 articles and documents

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.

Ruthenium-Catalyzed Diastereoselective syn-Cyclopropanation of Trisubstituted Alkenes with Diazoacetates

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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.