Ethyl 2-cyano-3-oxobutanoate

Base Information

• Chemical Name: Ethyl 2-cyano-3-oxobutanoate
• CAS No.: 634-55-9
• Molecular Formula: C7H9NO3
• Molecular Weight: 155.153
• Hs Code.: 2926909090
• European Community (EC) Number: 700-172-3
• DSSTox Substance ID: DTXSID40979569
• Nikkaji Number: J396.803K
• Wikidata: Q27122992
• Metabolomics Workbench ID: 57970
• Mol file: 634-55-9.mol

Synonyms:Ethyl 2-cyanoacetoacetate;634-55-9;Ethyl 2-cyano-3-oxobutanoate;ETHYL 2-ACETYLCYANOACETATE;Ethyl2-acetylcyanoacetate;Ethyl a-cyanoacetoacetate;Butanoic acid, 2-cyano-3-oxo-, ethyl ester;Ethyl alpha-cyanoacetoacetate;2-cyanoacetoacetic acid ethyl ester;EC 700-172-3;2-cyano-3-oxo-butyric acid ethyl ester;Ethyl 2-cyanoacetoactate;Ethyl .alpha.-cyanoacetoacetate;SCHEMBL3975055;CHEBI:51924;Ethyl 2-cyano-3-oxobutanoate #;DTXSID40979569;MFCD00043487;AKOS006220907;ethyl 2-cyanoacetoacetate, AldrichCPR;2-Cyano-3-oxobutyric acid ethyl ester;Acetoacetic acid, 2-cyano-, ethyl ester;AS-49426;CS-0151901;FT-0625913;I10196;Q27122992

Chemical Property of Ethyl 2-cyano-3-oxobutanoate

Chemical Property:

• Appearance/Colour: Liquid
• Vapor Pressure: 0.11mmHg at 25°C
• Refractive Index: 1.435
• Boiling Point: 220.9 °C at 760 mmHg
• PKA: 4.58±0.46(Predicted)
• Flash Point: 91.2 °C
• PSA: 67.16000
• Density: 1.12 g/cm³
• LogP: 0.27828
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 155.058243149
• Heavy Atom Count: 11
• Complexity: 213

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl2-Cyano-3-oxobutanoate ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22-41
• Safety Statements: 26-36/37/39-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C#N)C(=O)C
• Uses: It is used as a pharmaceutical intermediate. It is also used in the synthesis of fluorine-containing alkyl 2-cyano-3-oxocarboxylates and also in the syntheses of pyrazolo [1, 2-a] pyrazole and pyrazolo [5, 1-b] [1, 3] oxazine derivatives.

Technology Process of Ethyl 2-cyano-3-oxobutanoate

There total 15 articles about Ethyl 2-cyano-3-oxobutanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

5-methylisoxazole-4-carboxylic acid ethyl ester (51135-73-0) → ethyl 2-cyanoacetoacetate (634-55-9)

Guidance literature:

With sodium ethanolate; In diethyl ether; ethanol; for 12h; Ambient temperature;

Reference yield: 90.0%

acetyl chloride (75-36-5) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanoacetoacetate (634-55-9)

Guidance literature:

ethyl 2-cyanoacetate; With ethanol; magnesium; In tetrachloromethane; toluene; for 1h; Heating;

acetyl chloride; In tetrachloromethane; toluene; at 0 - 20 ℃; for 1.5h;

DOI:10.3987/COM-04-10216

Reference yield:

2-(amino-cyano-methylen)-acetoacetic acid ethyl ester (90281-20-2) → hydrogen cyanide (74-90-8) + ethyl 2-cyanoacetoacetate (634-55-9)

Guidance literature:

2--acetoacetic acid ethyl ester, α-form;

upstream raw materials:

pyridine

acetyl chloride

ethyl 2-cyanoacetate

5-methylisoxazole-4-carboxylic acid ethyl ester

Downstream raw materials:

5-amino-3-methyl-4-isoxazolecarboxylic acid ethyl ester

2-cyano-3-hydrazino-crotonic acid hydrazide

ethyl phenylazocyanoacetate

chloroethane

Refernces

• 1、 Burdelt,Rogers. "-". . p. 2105. Retrieved 1964.
• 2、 Hosseini, Yaser,Rastgar, Saeed,Zerrin Heren,Orhan Büyükgüng?r,Pesyan, Nader Noroozi. "One-pot new barbituric acid derivatives derived from the reaction of barbituric acids with BrCN and ketones". experimental part. p. 309 - 318. Retrieved 2011/11/06.
• 3、 Schenone, Pietro,Fossa, Paola,Menozzi, Giulia. "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 ". . p. 453 - 457. Retrieved 2007/10/02.