631-22-1

Usage

Uses

Used in Chemical Synthesis:
DIETHYL DIBROMOMALONATE is used as a key intermediate in the synthesis of various chemical compounds, including dibromonorcarane and allyl-substituted esters. Its reactivity with sodium methoxide and allyl(pyridine)cobaloximes makes it a valuable component in the production of these compounds.
Used in Pharmaceutical Industry:
DIETHYL DIBROMOMALONATE is used as a building block in the development of pharmaceutical compounds. Its ability to form dibromonorcarane and allyl-substituted esters can contribute to the creation of new drugs with potential therapeutic applications.
Used in Research and Development:
DIETHYL DIBROMOMALONATE is utilized in research and development settings to explore its potential applications and reactions with other compounds. This can lead to the discovery of new chemical processes and the development of innovative products in various industries.

InChI:InChI=1/C7H10Br2O4/c1-3-12-5(10)7(8,9)6(11)13-4-2/h3-4H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 141-82-2 malonic acid 
• 105-53-3 diethyl malonate 
• 81289-78-3 diethyl chlorobromomalonate 
• 32002-24-7 ethyl 3,3-diethoxyacrylate 
• 7726-95-6 bromine 
• 116-15-4 perfluoropropylene 
• 685-87-0 Diethyl 2-bromomalonate 
• 7732-18-5 water 

Downstream Products

• 609-09-6 Diethyl ketomalonate 
• 4525-71-7 diphenoxy-malonic acid diethyl ester 
• 6174-95-4 1,1,2,2-tetracarboethoxy-ethylene 
• 1071713-96-6 bis-m-tolyloxy-malonic acid diethyl ester 
• 859200-41-2 bis-p-tolyloxy-malonic acid diethyl ester 
• 42760-94-1 bis-(4-nitro-phenoxy)-malonic acid diethyl ester 
• 105-58-8 Diethyl carbonate 
• 34453-93-5 2-(Acetoxy-phenyl-methyl)-2-bromo-malonic acid diethyl ester 
• 6327-84-0 diethyl trans-2-benzoyl-3-phenylcyclopropane-1,1-dicarboxylate 
• 51615-51-1 trans-2-acetyl-3-phenylcyclopropane-1,1-dicarboxylate de diethyle 
• 3092-20-4 diethyl 2-phenylcyclopropane-1,1-dicarboxylate 
• 74444-83-0 2-(4-chlorophenyl)cyclopropane-1,1-dicarboxylic acid diethyl ester 
• 75228-42-1 diethyl trans-2-methyl-3-phenyl-1,1-cyclopropanedicarboxylate 
• 75228-42-1 diethyl cis-2-methyl-3-phenyl-1,1-cyclopropanedicarboxylate 

Relevant academic research and scientific papers

Base-mediated reactions of diethyl malonates derivatives with perfluorinated olefins: Novel synthetic routes to multifunctional ionomer precursors

A novel synthetic method for the preparation of per- and polyfluorinated unsaturated 2-substituted malonates is presented involving the deprotonation of the starting diethyl malonate by a strong base, followed by in situ addition of the C-nucleophile to the terminal double bond of the perfluorinated olefin. Subsequent elimination of the corresponding leaving groups and restoring of the double bond leads to the target bifunctional perfluorinated olefins. In the case of unsubstituted diethyl malonate, the elimination is accompanied by a prototropic rearrangement with a double bond migration and the addition of a second equivalent of the C-nucleophile forming the tetrafunctional internal olefins. The reaction conditions, factors affecting the reactivity and regioselectivity of the process, the choice of reagent as well as the course of competitive reactions are also discussed.

Synthetic method of alpha-position dibromination of alpha-heterocyclic carbonyl compound

The invention discloses a synthetic method of alpha-position dibromination of an alpha-heterocyclic carbonyl compound, and belongs to the technical field of organic synthesis, and the method comprisesthe following steps: by taking the alpha-heterocyclic carbonyl compound as a raw material, adding a bromination reagent, a solvent and a small molecular catalyst, and reacting under light irradiationto obtain a corresponding product. The method has the advantages of high yield, simplicity and convenience in operation, mild reaction conditions, wide substrate adaptability and the like.

Alkyl Halides via Visible Light Mediated Dehalogenation

Net selective bromination and chlorination of activated C-H bonds can be effected in generally high yield via a simple perhalogenation/dehalogenation sequence. The photochemical reductions require no photocatalyst, relying instead on the formation of an electron donor-acceptor complex of the substrate and reductant, or alternatively autophotocatalysis. Some reactions proceed despite any apparent photon absorption, serving as a cautionary tale for other photochemical reactions involving amines. Mechanistic experiments provide an explanation for this observation.

Reaction of the C60 radical anion with alkyl halides

The reaction of the C60 radical anion (C60-) with α-bromo-1,3-dicarbonyl compounds selectively afforded the methanofullerene derivatives. The reaction with benzyl halide and 1,2-bis(dihalomethyl)benzene afforded the corresponding 1,4-dibenzylated C60 derivative and cycloaddition product, respectively. The possible mechanisms for the formation of the fullerene adducts are proposed.

Solvent-Controlled α-Monobromination, α,α-Dibromination or Imidation of 1,3-Diketones with N-Bromosuccinimide

In this work, we present a solvent-controlled regioselective method for α-monobromination, dibromination or imidation of 1,3-diketones with N-bromosuccinimide under simple reaction conditions. The employment of solvents plays a key role on the reaction selectivity providing α-monobrominated, dibrominated and imidated products. Visible light irradiation accelerates the dibromination reaction of 1,3-diketones. In particular, one important solvent was found to be highly effective for the imidation of 1,3-diketones under base-free condition.

Preparation method of 2,2-dihalo-1,3-dicarbonyl derivatives

The invention discloses a method for preparing 2,2-dihalo-1,3-dicarbonyl derivatives. The method is widely applicable to 1,3-dicarbonyl derivatives. The raw materials are easily available, and types are multiple. Types of products obtained by the method are multiple, and the products can be directly used or used in other further reactions. The method has advantages of mild reaction condition, simple reaction operation and post-processing, short reaction time, high yield and little pollution, and is suitable for industrial production.

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.

Conversion of nucleophilic halides to electrophilic halides: Efficient and selective halogenation of azinones, amides, and carbonyl compounds using metal halide/lead tetraacetate

AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc) 4 are efficient electrophilic N- and α-C-halogenating agents. A variety of azinones, amides and carbonyl compounds were chemoselectively and regioselectively N-, or α-C-halogenated in good to excellent yield using AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc)4 in acetonitrile. Georg Thieme Verlag Stuttgart.

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.

N,N-Dibromobenzenesulfonamide: A useful regenrable reagent for bromination of various carbanionic substrates

N,N-Dibromobenzenesulfonamide(dibromoamine-B), which is prepared easily in high yield, has been employed as effective brominating agent for carbanionic substrates under mild conditions. β-Diketones and β-ketoesters were brominated by this reagent without using any bases. The reagent can be recovered, rebrominated, and reused several times.