34243-82-8

Basic information

• Product Name: Cyclohexanecarboxylic acid, 1-bromo-2-oxo-, ethyl ester
• Synonyms: Cyclohexanecarboxylic acid,1-bromo-2-oxo-,ethyl ester;ethyl 1-bromo-2-oxocyclohexanecarboxylate;1-Brom-2-oxo-cyclohexancarbonsaeure-aethylester;2-Brom-2-aethoxycarbonylcyclohexanon;1-bromo-2-oxo-cyclohexanecarboxylic acid ethyl ester
• CAS NO: 34243-82-8
• Molecular Formula: C9H13BrO3
• Molecular Weight: 249.104
• Mol File: 34243-82-8.mol

Chemical Properties

• CAS DataBase Reference: Cyclohexanecarboxylic acid, 1-bromo-2-oxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid, 1-bromo-2-oxo-, ethyl ester(34243-82-8)
• EPA Substance Registry System: Cyclohexanecarboxylic acid, 1-bromo-2-oxo-, ethyl ester(34243-82-8)

Safety Data

• Hazardous Substances Data: 34243-82-8(Hazardous Substances Data)

Upstream product

• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 128-08-5 N-Bromosuccinimide 

Downstream Products

• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 38167-88-3 7-carboethoxy-tetrahydro-2(3H)-azepinone 
• 251095-04-2 ethyl 1-azido-2-oxocyclohexane-1-carboxylate 
• 3400-80-4 ethyl 2-oxocyclohex-3-ene-1-carboxylate 
• 57205-09-1 ethyl 6-oxocyclohex-1-enecarboxylate 

Relevant articles and documents

A mild and regioselective method for α-bromination of β-keto esters and 1,3-diketones using bromodimethylsulfonium bromide (BDMS)

Bromodimethylsulfonium bromide has been found to be an effective and regioselective reagent for α-monobromination of β-keto esters and 1,3-diketones. A wide variety of β-keto esters and 1,3-diketones undergo chemoselective α-monobromination with excellent yields at 0-5 °C or room temperature. The notable advantages of this protocol are no need of chromatographic separation, use of less hazardous reagent than molecular bromine, and no added base, Lewis acid, or other catalyst.

Chemoselective bromination of active methylene and methyne compounds by potassium bromide, hydrochloric acid and hydrogen peroxide

Active methylene and methyne compounds can be chemoselectively brominated in high yields using potassium bromide, hydrochloric acid, and hydrogen peroxide at room temperature. Georg Thieme Verlag Stuttgart.

Halide and preparation method thereof, composition for preparing halide and halogenating reaction

The invention provides a halide for a halogenating reaction. The halide is used for providing a halogen in the halogenating reaction, the halide comprises any one of compounds shown in a formula I ora formula II or a formula III, in the formula I or the formula II or the formula III, the R group comprises any one of hydrogen or the halogen or an alkyl group or an aryl group or a nitro group, X comprises any one of F or Cl or Br or I, and M comprises any one of tetra-allkylammonium cation, Li, Na, K, Rb and Cs. The invention further provides a preparation method of the halide, a composition for preparing the halide and the halogenating reaction. Accordingly, normal-temperature and additive-free halogenation on the compounds can be achieved, and then products high in yieldand chemoselectivity are obtained; due to the fact that by-products generated after the halide is subjected to a corresponding reaction is likely to be dissolved into water, the corresponding products are likely to be separated and purified.

Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones

This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones.

PPh3·HBr-DMSO: A Reagent System for Diverse Chemoselective Transformations

The broad applicability of the hitherto unexplored reagent combination PPh3·HBr-DMSO is exemplified with multiple highly diverse one-step transformations to synthetically useful building blocks, such as flavones, 4H-thiochromen-4-ones, α-hydroxy ketones, 1,4-naphthoquinones (including vitamin K3), 2-bromo-3-substituted-1H-1-indenones, 2-methylthio-1H-1-indenones, 3-butyne-1,2-dione, and 4-pentene-2,3-diones. The simple and mild reaction conditions make the reagent superior in terms of yield and substrate scope in comparison with the existing alternatives.

Novel Metal- and Mineral-Acid-Free Synthesis of Organic Ammonium Tribromides and Application of Ethylenephenanthrolium Bistribromide for Bromination of Active Methylene Group of 1,3-Diketones and β-Ketoesters

A novel procedure for the preparation of organic ammonium tribromides (OATBs) is described from their corresponding bromides. Quaternary ammonium bromides (QABs) and a N,N′-heterocyclic dibromide are efficiently oxidized to their corresponding monotribromides and bistribromide by m-chloroperbenzoic acid (MCPBA) in the presence of 2 and 4 equiv of KBr, respectively. The reactions are carried out in an aqueous medium without the use of any mineral acid or metal catalyst/promoters. A variety of tribromides are synthesized in very good yields including a hitherto unknown reagent, 1,10-(ethane-1, 2-diyl)phenanthrolinediium bistribromide (EPDBT). EPDBT is investigated as brominating agent and found to be highly effective for selective bromination of active methylene groups of a variety of 1,3-diketones and β-ketoesters. GRAPHICAL ABSTRACT.

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.

Sulfoxide-mediated Umpolung of alkali halide salts

A new protocol for the direct two-electron oxidative Umpolung of alkali halide salts is reported. This procedure, relying on the use of a commercially available sulfoxide as the oxidant, allows the electrophilic halogenation of carbonyl compounds as well as halolactonisation reactions to proceed from the corresponding sodium salts, at room temperature and under mild conditions.

Facile and efficient method for oc-monobromination of dicarbonyl compounds with N-bromosuccinimide

The a-monobrominated products were prepared fast in presence of p-TsOH as catalyst in very high yields using various 1,3-diketones and β-keto-esters with N-bromosuccinimide in CH2C12.

Hydrogen peroxide or peracetic acid mediated self-titrating α-halogenation of 1,3-dicarbonyl compounds

Efficient oxidative -halogenation of 1,3-dicarbonyl compounds has been achieved by employing a system comprising of sub-stoichiometric amounts of TiX4 (X = Cl, Br) in conjunction with environmentally benign hydrogen peroxide (H2Osub