89415-67-8

Usage

Appearance

Yellowish to brown-colored liquid Describes the physical appearance of the compound as a liquid with a yellowish to brown color.

Odor

Pungent Indicates that the compound has a strong, irritating smell.

Common uses

Intermediate in organic synthesis Used as a starting material or building block in the synthesis of other chemical compounds.

Primary applications

Production of pharmaceuticals and agrochemicals The compound is mainly used in the manufacturing of drugs and chemicals for agricultural purposes.

Reagent use

Synthesis of various esters and derivatives The compound serves as a reagent in organic chemical reactions, particularly in the formation of esters and their derivatives.

Hazard classification

Hazardous substance Indicates that the compound poses potential risks to human health and the environment.

Safety measures

Handle and store with appropriate precautions Emphasizes the need for proper handling and storage to minimize risks associated with the hazardous nature of the compound.

Upstream product

• 141-97-9 ethyl acetoacetate 
• 87413-09-0 Dess-Martin periodane 
• 7726-95-6 bromine 

Downstream Products

• 54023-37-9 ethyl 2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate 
• 92898-26-5 (E)-1-acetyl-1-(ethoxycarbonyl)-2-phenylcyclopropane 
• 92898-25-4 (Z)-1-acetyl-1-(ethoxycarbonyl)-2-phenylcyclopropane 
• 84911-18-2 ethyl 2-bromoacetoacetate 
• 141-97-9 ethyl acetoacetate 
• 5870-38-2 diethyl 2,5-(dihydroxy)terephthalate 

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.

Lipophilic indole mediated chemoselective α-monobromination of 1,3-dicarbonyl compounds

A mild and efficient mono-selective bromination of 1,3-dicarbonyl compounds has been developed using lipophilic indole catalysts. Inexpensive and commercially available N-bromosuccinimide (NBS) was used as the brominating reagent. The selectivity was further enhanced when using stoichiometric amount of 3-bromoindole species. Mechanistic studies reveal that the indole catalyst has dual functions in the mono-bromination process.

A mild CuI-catalyzed Glaser-type homo-coupling reaction using α,α-dibromo-β-dicarbonyl compounds as oxidants

Exploration of α,α-dibromo-β-dicarbonyl compounds as novel organic oxidants for the mild Cu(I)-catalyzed Glaser-type homo-coupling reaction has been achieved, which provides an alternatively efficient pathway for the construction of 1,3-conjugated structures. In addition, the mechanism of this reaction was investigated.

A mild and efficient method for bromination of alcohols using α,α-dibromo-β-dicarbonyl compounds as halogen sources

Exploration of α,α-dibromo-β-dicarbonyl compounds as novel bromine agents for the conversion of alcohols to alkyl bromides under neutral conditions has been achieved. This method can be used for acid-sensitive substrates and allows the bromination of various primary and secondary alcohols to proceed at room temperature within a very short period of time.

Oxidative bromination of ketones using ammonium bromide and oxone

A highly efficient, environmentally safe and economic method for selective α-monobromination of aralkyl, cyclic, acyclic, 1,3-diketones and β-keto esters and α,α-dibromination of 1,3-diketones and β-keto esters without catalyst is reported using ammonium bromide as a bromine source and oxone as an oxidant. The reaction proceeds at ambient temperature and yields range from moderate to excellent. Bromination of unsymmetrical ketones takes place at the less substituted α-position predominantly. Aromatisation of tetralones is also carried out with this reagent system.

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.

α-bromination of 1,3-dicarbonyl compounds using Dess-Martin periodinane (DMP) and tetraethylammonium bromide (TEAB)

A mild and expeditious method for α-bromination of 1,3-dicarbonyl compounds using Dess-Martin periodinane and tetraethylammonium bromide is described. Copyright Taylor & Francis Group, LLC.

A mild and environmentally acceptable synthetic protocol for chemoselective α-bromination of β-keto esters and 1,3-diketones

A wide variety of unsubstituted β-keto esters can be brominated chemoselectively to the corresponding α-monobromo-β-keto esters by using a combination of vanadium pentoxide, hydrogen peroxide and ammonium bromide in a biphasic system, dichloromethane-wate

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.