634-55-9

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-CYANOACETOACETATE is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique structure allows it to be a valuable building block in the development of new pharmaceutical compounds.
Used in Synthesis of Fluorine-Containing Compounds:
In the field of organic chemistry, ETHYL 2-CYANOACETOACETATE is used in the synthesis of fluorine-containing alkyl 2-cyano-3-oxocarboxylates. These compounds have potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science, due to the unique properties conferred by fluorine atoms.
Used in Synthesis of Pyrazolo Derivatives:
ETHYL 2-CYANOACETOACETATE is also utilized in the syntheses of pyrazolo[1,2-a]pyrazole and pyrazolo[5,1-b][1,3]oxazine derivatives. These heterocyclic compounds have potential applications in medicinal chemistry, as they can exhibit a range of biological activities, such as anticancer, antiviral, and anti-inflammatory properties.

InChI:InChI=1/C7H9NO3/c1-3-11-7(10)6(4-8)5(2)9/h6H,3H2,1-2H3/t6-/m1/s1

Upstream product

• 110-86-1 pyridine 
• 75-36-5 acetyl chloride 
• 105-56-6 ethyl 2-cyanoacetate 
• 108-24-7 acetic anhydride 
• 463-51-4 Ketene 
• 90281-20-2 2-(amino-cyano-methylen)-acetoacetic acid ethyl ester 
• 506-68-3 bromocyane 
• 141-97-9 ethyl acetoacetate 
• 134653-70-6 ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate 
• 51135-73-0 5-methylisoxazole-4-carboxylic acid ethyl ester 
• 506-77-4 cyanogen chloride 
• 141-52-6 sodium ethanolate 

Downstream Products

• 75-00-3 chloroethane 
• 124-38-9 carbon dioxide 
• 64-19-7 acetic acid 
• 121716-27-6 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 84661-50-7 5-amino-3-methyl-1,2-oxazole-4-carboxylic acid 
• 5335-36-4 ethyl phenylazocyanoacetate 
• 131455-45-3 2-cyano-3-hydrazino-crotonic acid hydrazide 
• 25786-72-5 5-amino-3-methyl-4-isoxazolecarboxylic acid ethyl ester 

Relevant academic research and scientific papers

Flash preparation of carbenoids: A different performance of cyanogen bromide

Cyanogen halides are known substances for the cyanating reaction. There are a few evidences for bromination reaction too. On the other hand carbenes are known as very important substances due to their remarkable reactions. Unfortunately carbenes at room temperature are very unstable and there is not a simple method for preparation of them. In most cases the isolation is not possible. We have reported a new reliable and fast preparation method of almost stable carbenoids. The mechanism of the formation has been discussed.

One-pot new barbituric acid derivatives derived from the reaction of barbituric acids with BrCN and ketones

Reaction of cyclic β-dicarbonyl compounds such as pyrimidine-(1 H,3H,5H)-2,4,6-trione (BA), 1,3-dimethyl pyrimidine-(1 H,3H,5H)-2,4,6-trione (DMBA) and 2-thioxo-pyrimidine-(1 H,3H,5H)-4,6-dione (TBA) with cyanogen bromide in acetone and 2-butanone in the presence of triethylamine afforded a new class of stable heterocyclic spiro[furo[2,3-d]pyrimidine-6,5′-pyrimidine]2, 2′,4,4′,6′(3H,3′H,5H)-penta-ones (dimeric forms of barbiturate) at 0 °C and ambient temperature. Structure elucidation was carried out by X-ray crystallographic, 1H NMR, 13C NMR, two dimensional NMR, FT-IR spectra, mass spectrometry and elemental analysis. The mechanism of product formation is discussed. The reaction of DMBA with cyanogen bromide in the presence of triethylamine also afforded trimeric form of barbiturate of uracil derivatives in good yield. The reaction of selected acyclic β-dicarbonyl compounds with cyanogen bromide in the presence of triethylamine in acetone and/or diethyl ether has also been investigated under the same condition. Diethyl malonate and ethyl cyanoacetate brominated and also ethyl acetocetate both bro-minated and cyanated on active methylene via cyanogen bromide.

Synthesis and cyclization reaction of pyrazolin-5-one derivatives

A versatile synthetic method for preparing 3-pyrazolin-5-ones and 5,8-dihydro-1H-pyrazolo[1,2-a]pyridazines from simple β-keto esters is demonstrated. The synthetic strategies involve the acylation of β-keto esters, cyclocondensation with hydrazine followed by trapping with a diene under oxidative conditions.

Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles. X. Synthesis of 5-Substituted Ethyl or Methyl 4-Isoxazolecarboxylates and Methyl 4-(2,2-Dimethyl-1-oxopropyl)-5-isoxazolecarboxylate

Reaction of ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates with hydroxylamine hydrochloride in methanol solution afforded in high yields the relative esters of 5-substituted 4-isoxazolecarboxylic acids II.These esters were hydrolyzed generally with concentrated hydrochloric acid-acetic acid mixtures to the corresponding carboxylic acids in satisfactory yields.Ethyl or methyl esters II isomerized with sodium ethoxide or methoxide, respectively, to the corresponding esters or hemiesters of 2-cyano-3-oxoalkanoic acids generally in excellent to satisfactory yields.Reaction of methyl 5,5-dimethyl-3-dimethylaminomethylene-2,4-dioxohexanoate with hydroxylamine hydrochloride afforded in moderate yield methyl 4-(2,2-dimethyl-1-oxopropyl)-5-isoxazolecarboxylate, which was converted by acid hydrolysis as above to 4-t-butyl-4-hydroxyfuroisoxazol-6-(4H)-one.