1447-13-8

Basic information

• Product Name: METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE
• Synonyms: METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE;1-Methyl-2,2-dichlorocyclopropane-1-carboxylic acid methyl ester;2,2-Dichloro-1-methyl-1-cyclopropanecarboxylic acid methyl ester;2,2-Dichloro-1-methylcyclopropanecarboxylic acid methyl ester;2,2-Dichloro-1-methylcyclopropane-carboxylic acid methyl ester;methyl 2,2-dichloro-1-methyl-cyclopropane-1-carboxylate;methyl 2,2-dichloro-1-methylcyclopropane-1-carboxylate;Methyl 2,2-dichloro-1-Methyl-cyclopropanecarbxoylate
• CAS NO: 1447-13-8
• Molecular Formula: C₆H₈Cl₂O₂
• Molecular Weight: 183.03
• EINECS: 215-900-0
• Product Categories: C6 to C7;Carbonyl Compounds;Esters
• Mol File: 1447-13-8.mol

Chemical Properties

• Boiling Point: 184-187 °C
• Flash Point: 74 °C
• Appearance: /
• Density: 1.269 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.347mmHg at 25°C
• Refractive Index: n20/D 1.463
• BRN: 1938341
• CAS DataBase Reference: METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE(1447-13-8)
• EPA Substance Registry System: METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE(1447-13-8)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1447-13-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE is used as an intermediate in the chemical synthesis industry for the production of various compounds. Its unique structure allows it to participate in a range of reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE is used as a building block for [creation of new molecules] in the chemical synthesis process due to [its reactivity and structural properties].
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE is used as a key component in the development of new drugs. Its unique chemical properties enable it to be incorporated into the molecular structures of potential therapeutic agents, contributing to the discovery of novel medications.
METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE is used as a pharmaceutical intermediate for [development of new drugs] because of [its compatibility with various molecular structures and its ability to enhance drug properties].
Used in Agrochemical Industry:
METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE also finds application in the agrochemical industry, where it is utilized in the synthesis of new pesticides and other agricultural chemicals. Its versatility in chemical reactions allows for the creation of compounds that can effectively target pests and diseases, improving crop yields and food security.
METHYL 2,2-DICHLORO-1-METHYLCYCLOPROPANECARBOXYLATE is used as a chemical intermediate in the agrochemical industry for [development of new pesticides and agricultural chemicals] to [enhance crop protection and increase yield].

Synthesis Reference(s)

Synthetic Communications, 12, p. 1163, 1982 DOI: 10.1080/00397918208065984

InChI:InChI=1/C6H8Cl2O2/c1-5(4(9)10-2)3-6(5,7)8/h3H2,1-2H3

Upstream product

• 67-66-3 chloroform 
• 80-62-6 methacrylic acid methyl ester 
• 20101-83-1 methyl 2-methyl-4,4,4-trichlorobutyrate 
• 186581-53-3 diazomethane 
• 1447-14-9 2,2-dichloro-1-methylcyclopropanecarboxylic acid 

Downstream Products

• 6914-76-7 1-Methyl-cyclopropanoic acid 
• 85393-10-8 2,2-dichloro-1-methylcyclopropane-1-carbaldehyde 
• 132277-00-0 (2,2-Dichloro-1-methylcyclopropyl)diphenylmethanol 
• 6206-25-3 methyl 1-methylcyclopropanecarboxylate 

Relevant articles and documents

FORMATION OF A REASONABLY STABILIZED TRICHLOROMETHYL ANION BY THE REACTION OF CHLOROFORM WITH ELECTROGENERATED BASE, AND ITS 1,4-ADDITION TO α,β-UNSATURATED CARBONYL COMPOUNDS

A reasonably stabilized trichloromethyl anion (TCMA) was formed by the reaction of chloroform with an electrogenerated base prepared by the electroreduction of 2-pyrrolidone, and the addition of this TCMA to α,β-unsaturated esters gave the corresponding β-trichloromethyl esters in good yields.

A process for preparing 1-methyl propyl formic acid method

The invention discloses a method for preparing 1-methyl cyclopropane carboxylic acid and belongs to the fields of fine chemical engineering and medical intermediates. The method comprises the following steps: by taking methacrylic acid (ester or salt), or methacrylonitrile or methacrylamide as a raw material, carrying out a cyclopropanation reaction with trihalide in the presence of an alkali to generate 2,2-geminal halide (III); carrying out a reaction between the 2,2-geminal halide (III) and metallic sodium to remove halogen atoms on the ring so as to generate methyl cyclopropionate or methyl cyclopropaneacetonitrile or methyl cyclopropylamide (II); acidifying the methyl cyclopropanecarboxylate, thereby obtaining 1-methyl cyclopropane carboxylic acid (I); and performing basic hydrolysis on methyl cyclopropaneacetonitrile or methyl cyclopropylamide, and acidifying to obtain 1-methyl cyclopropane carboxylic acid (I). The method disclosed by the invention is readily available in raw materials, mild in reaction conditions, convenient to operate, low in cost and high in purity of the obtained product and is a feasible preparation method.

Phase transfer catalyzed reactions of chloroform with methacrylic esters

Chloroform reacts with an excess of methyl methacrylate in the presence of 50% aq NaOH and benzyltriethylammonium chloride (TEBA) as a catalyst (phase transfer catalysis, PTC) to give a mixture of dichlorocarbene and trichloromethyl anion adducts, 1 and 2, respectively. These additions proceed as parallel processes, there is a slow conversion of 2 → 1, which proceeds as an intramolecular process.

Phase transfer catalyzed reactions of chloroform with electrophilic alkenes. Effect of solvent on reaction course

Reaction of chloroform with acrylic esters 1a-g, carried out in the presence of 50% aq NaOH, benzyltriethylammonium chloride (TEBACl) as a catalyst in heptane, gives exclusively adducts of trichloromethyl anion 2a-g with good yields. The same reaction carried out in the absence of solvent yields a mixture of products.