1187-46-8

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 2-bromo-2-cyano-acetate is used as a key intermediate for the synthesis of active pharmaceutical ingredients, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
Ethyl 2-bromo-2-cyano-acetate is utilized as a reagent in the preparation of various agrochemical compounds, aiding in the creation of products for agricultural applications.
Used in Organic Synthesis:
Ethyl 2-bromo-2-cyano-acetate is employed as a versatile reagent in organic synthesis, facilitating the formation of carbon-carbon and carbon-nitrogen bonds, which are crucial in the construction of complex organic molecules.

InChI:InChI=1/C5H6BrNO2/c1-2-9-5(8)4(6)3-7/h4H,2H2,1H3

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 35768-29-7 ethyl 3-(4-chlorophenyl)-2-cyanooxirane-2-carboxylate 
• 134890-52-1 ethyl 2-cyano-3-(4-methylphenyl)oxirane-2-carboxylate 
• 13280-85-8 ethyl 2,2-dibromo-2-cyanoacetate 
• 292638-85-8 acrylic acid methyl ester 
• 18852-51-2 sodium cyanoacetic acid ethyl ester 

Downstream Products

• 24612-13-3 1.2.2-Tricyan-3-<4-methoxy-phenyl>-cyclopropan-1-carbonsaeure-ethylester 
• 23993-30-8 4-amino-2-imino-3-m-tolyl-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 23993-24-0 4-amino-3-p-tolyl-5-carbethoxy-2-imino-4-thiazoline 
• 23993-27-3 4-amino-3-o-tolyl-5-carbethoxy-2-imino-4-thiazoline 
• 23993-31-9 4-amino-3-(3-chloro-phenyl)-2-imino-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 23993-26-2 4-amino-3-(4-ethoxy-phenyl)-2-imino-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 339559-48-7 4-amino-3-(4-bromo-phenyl)-2-imino-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 14561-99-0 diethyl 1,2-dicyano-3-phenyl-1,2-cyclopropanedicarboxylate 
• 23993-25-1 4-amino-2-imino-3-(4-methoxy-phenyl)-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 23993-29-5 4-amino-2-imino-3-(2-methoxy-phenyl)-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 24064-22-0 4-amino-3-(4-chloro-phenyl)-2-imino-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 125909-80-0 1-pentafluorophenyl-3-phenyl-5-ethoxycarbonyl-1,2,4-triazole 
• 35234-88-9 diethyl dicyanofumarate 
• 144558-71-4 2-[1-(Cyano-ethoxycarbonyl-methylsulfanyl)-1-phenylamino-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester 

Relevant academic research and scientific papers

Ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB): An efficient reagent for the monobromination of 1,3-diketones and β-ketoesters

Ethylenebis(N-methylimidazolium) ditribromide, a stable crystalline solid, is easily prepared by reaction of the corresponding dibromide salt with bromine in n-hexane. 1,3-Diketones and β-ketoesters can be brominated chemoselectively to the corresponding α-monobrominated products by using this reagent at 0-5°C. Under the same reaction conditions, diethyl malonate, ethyl cyanoacetate, and malonitrile were monobrominated at moderate yield.

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.

Selective monobromination of 1,3-diones with N-bromosaccharin/Mg(ClO 4)2 system in solution and under solvent-free conditions

N-Bromosaccharin/Mg(ClO4)2 is an effective and regioselective system for α-monobromination of 1,3-dicarbonyl compounds. A wide variety of β-keto esters and 1,3-diketones in reaction with this system afforded a regioselectively α-mono

Tetrameric DABCO-bromine: An efficient and versatile reagent for bromination of various organic compounds

Tetrameric DABCO-bromine is a powerful brominating agent but shows reasonable selectivity with certain substrates. The selective bromination for activated aromatic compounds and alkenes is reported. Synthesis of α-bromo ketones and nitriles has also been achieved by using this reagent and the results are also reported. All products reported were obtained in good to excellent yields.

Poly(vinylpyrrolidone)-bromine complex; a mild and efficient reagent for selective bromination of alkenes and oxidation of alcohols

Poly(vinylpyrrolidone)-bromine complex (PVP-Br2) is easily prepared and used as a mild and convenient reagent for selective bromination of alkenes and at the position α-hydrogen of active carbonyl compounds. Selective oxidation of benzylic alcohols in the presence of aliphatic alcohols were also achieved at room temperature.

Reaction of Li2NiBr4/THF with oxiranes: unexpected behavior of glycidic esters

The complex Li2NiBr4/THF usually gives bromohydrins from epoxides but reacts with α-ester epoxides or α-keto epoxides to generate a carbene species which was trapped with maleimide. - Keywords: epoxides / carbenes / dilithium tetrabromonickelate

A Convenient Synthesis of Dialkyl (E)-2,3-Dicyanobutendioates

Dialkyl (E)-2,3-dicyanobutendioates 4, potentially useful intermediates for the synthesis of a wide variety of heterocyclic compounds, are conveniently prepared by the reaction of alkyl bromocyanoacetates 2 with potassium thiocyanate in acetonitrile followed by treatment with water.The starting alkyl bromocyanoacetates are prepared by the photochemical reaction of the appropriate alkyl cyanoacetate with bromine in carbon tetrachloride.

TRIBUTYLSTIBINE MEDIATED SYNTHESIS OF 1,1,2-TRI-SUBSTITUTED CYCLOPROPANES

A novel method for the synthesis of 1,1,2-tri-substituted cyclopropanes is reported which involves the reaction of electron-deficient olefins with dibromomalonic ester, dibromocyanoacetic or dibromobenzeneacetic ester promoted by tri-n-butylstibine.The reaction was carried out under mild conditions to give the cyclopropane derivatives in moderate to good yields.Other R3M (M= As,Sb,Bi) reagents as promoter for this reaction have been studied and seem to be less effective than tributylstibine.

Reactions of Perfluoroalkanesulfonyl Bromide

Perfluoroalkanesulfonyl bromides were readily prepared from the reaction of the corresponding sodium sulfinates with bromine in aqueous solution in excellent yield.Several reactions of these sulfonyl bromides were reported: 1.Spontaneous addition to olefin with the loss of sulfur dioxide to give the corresponding adducts in good yield. 2.Facile bromination of compounds containing active hydrogen. 3.Reaction with alcohol, amines and alkali.