6134-66-3

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 2,2-dichloroacetoacetate is used as a key intermediate for the synthesis of various pharmaceutical products. Its versatile reactivity allows for the creation of a wide range of medicinal compounds, contributing to the development of new treatments and therapies.
Used in Agrochemical Industry:
Ethyl 2,2-dichloroacetoacetate is utilized as an intermediate in the production of agrochemicals. Its chemical properties enable the synthesis of effective compounds for use in agriculture, such as pesticides and herbicides, to protect crops and enhance yields.
Used in Flavors and Fragrances Industry:
Ethyl 2,2-dichloroacetoacetate is employed as a building block in the creation of flavors and fragrances. Its ability to participate in various chemical reactions allows for the development of unique and complex scents and tastes for use in the food, beverage, and cosmetic industries.
Used in Organic Synthesis:
Ethyl 2,2-dichloroacetoacetate is used as a reagent in organic synthesis. Its diverse reactivity makes it a valuable component in the synthesis of a broad spectrum of organic compounds, facilitating advancements in chemical research and development.

InChI:InChI=1/C6H8Cl2O3/c1-3-11-5(10)6(7,8)4(2)9/h3H2,1-2H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 515-84-4 Ethyl trichloroacetate 
• 108-24-7 acetic anhydride 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 121-44-8 triethylamine 

Downstream Products

• 19559-59-2 potassium dichloroacetate 
• 141-78-6 ethyl acetate 
• 56267-60-8 2,5-Bis-[1-chloro-hept-(Z)-ylidene]-cyclohexane-1,4-dione 
• 56267-58-4 2-[1-Chloro-prop-(Z)-ylidene]-5-[1-chloro-prop-(E)-ylidene]-cyclohexane-1,4-dione 
• 56267-59-5 2,5-Bis-[1-chloro-2-methyl-prop-(Z)-ylidene]-cyclohexane-1,4-dione 
• 20375-16-0 3-phenyl-3-chloro-2-ketopropionic acid ethyl ester 
• 64-17-5 ethanol 
• 513-88-2 1,1-Dichloroacetone 
• 124-38-9 carbon dioxide 
• 60-35-5 acetamide 
• 1047675-53-5 ethyl 2-chloro-3-(2,6-difluorophenyl)oxirane-2-carboxylate 
• 85153-67-9 ethyl 2,2,4-trichloro-3-oxobutyrate 
• 68039-30-5 α,α-dichloro-γ-n-amylbutyrolactone 
• 78585-05-4 ethyl α-acetyl-α,γ-dichloropelargonate 

Relevant academic research and scientific papers

Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride

An efficient and facile method is reported for the synthesis of a series of α,α-dichloroketones. The direct dichlorination of methyl ketones and 1,3-dicarbonyls using an excess amount of sulfuryl chloride affords the corresponding gem-dichloro compounds in moderate to excellent yields. Moreover, the protocol features high yields, broad substrate scope, and simple reaction conditions without using any catalysts and solvents.

Trimethylchlorosilane-Mediated Mild α-Chlorination of 1,3-Dicarbonyl Compounds Promoted by Phenyliodonium Diacetate

Trimethylchlorosilane was used as chlorine source for the α-chlorination of 1,3-dicarbonyl compounds with phenyliodonium diacetate as oxidant at room temperature. The reaction allows the selective synthesis of α-monochlorinated products from different kinds of 1,3-dicarbonyl compounds in good yield. The potential possibility of this conversion for bromination has also been investigated.

A simple, mild, and efficient method for the preparation of α,α-dichloroketones with DCDMH catalyzed by ammonium chloride

New process that can selectively prepare α,α-dichloro ketones from various ketones with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) using ammonium chloride as a catalyst is reported. The effects of ammonium salts, solvents, DCDMH, and reaction temperature were investigated. Under the optimal condition, most of α,α-dichlorinated products were selectively obtained in 86-98% yield.

Mild and efficient α-chlorination of carbonyl compounds using ammonium chloride and oxone (2KHSO5·KHSO4· K2SO4)

A simple protocol for the α-monochlorination of ketones and 1,3-dicarbonyl compounds utilizing NH4Cl as a source of chlorine and Oxone as an oxidant in methanol without catalyst is presented. The reaction proceeds at ambient temperature in yields ranging from moderate to excellent.

Trihaloisocyanuric acids as convenient reagents for regioselective halogenation of β-dicarbonyl compounds

The reaction of β-dicarbonyl compounds (β-ketoesters and β-diketones) with 0.34 mol equiv of trichloro- and tribromoisocyanuric acids produced regioselectively the corresponding α-monohalo β-dicarbonyl compound. On the other hand, utilization of 0.68 mol equiv of the trihaloisocyanuric acid produced the α,α-dihalo β-dicarbonyl compound.

Simple and efficient methods for selective preparation of α-mono or α,α-dichloro ketones and β-ketoesters by using DCDMH

New processes that can selectively prepare α-mono or α,α-dichloro ketones and β-ketoesters using 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) are reported. Using silica gel as the catalyst and methanol as the solvent and heating for 1 h under reflux, α-monochlorinated products were selectively obtained in 86-98% yield. However using a deep eutectic solvent (choline chloride: p-TsOH = 1:1) as the solvent and stirring for 45 min at room temperature, α,α- dichlorinated products were selectively obtained in 86-95% yield.

An efficacious method for the halogenation of β-dicarbonyl compounds under mildly acidic conditions

A variety of 1,3-diketones, β-ketoesters and malonates can be chlorinated in high yields using sodium hypochlorite in a 5:2 mixture of acetone/acetic acid at 0°C for 1 h. Similarly, bromination of these dicarbonyl substrates can be accomplished under the same conditions using sodium hypobromite.

Selective preparation of α,α-dichloroketones with copper(II) chloride

Aryl and enolizable alkyl ketones react with copper(II) chloride in dimethylformamide to produce the corresponding α,α-dichloroketone in high yields. Remarkable qualities of the process are high selectivity towards these substrates, undetected polychlorinated by-products, easy work-up, commercially available reagents and HCl as the only waste stream.

CHLORINATION OF ACETYLACETONE AND ACETOACETIC AND MALONIC ESTERS.

To develop a laboratory procedure for the one-stage chlorination of ME, AAcE, and AA, the authors studied the action of gaseous chlorine on these compounds. We found that when the chlorination is carried out at 55-60 degree C, the formation of side products is reduced to a minimum. The reaction begins at 35-40 degree C, and then proceeds exothermally, and it can be easily controlled by external cooling or by decrease in the rate of chlorine input. The optimal reaction regime lies within 55-60 degree C. Further increase in temperature leads to the formation of trichloro derivatives and more extensive chlorination. If the chlorination reaction is carried out for 7-8 h at 55-60 degree C, dichloro derivatives of ME, AAcE, and AA are mainly formed, and the yields in the most favorable experiments are equal to (%): DCM 93, DCAAc 87, DCAA 75. Under these conditions, only inappreciable amounts of monochloro derivatives and more extensively chlorinated products are present in the reaction mixture. The authors isolated mono-, di-, and trichloro derivatives of ME, AAcE and AA.