Ethyl 2-acetyl-4-cyanobutyrate

Base Information

• Chemical Name: Ethyl 2-acetyl-4-cyanobutyrate
• CAS No.: 10444-33-4
• Molecular Formula: C9H13NO3
• Molecular Weight: 183.207
• Mol file: 10444-33-4.mol

Synonyms:1-cyano-4-oxo-3-pentanecarboxylate;2-<2-Cyano-ethyl>-3-oxo-butansaeureethylester;

Chemical Property of Ethyl 2-acetyl-4-cyanobutyrate

Chemical Property:

• PSA: 67.16000
• LogP: 1.05848

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl2-Acetyl-4-cyanobutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethyl 2-acetyl-4-cyanobutyrate

There total 7 articles about Ethyl 2-acetyl-4-cyanobutyrate 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: 88.0%

ethyl acetoacetate (141-97-9) + acrylonitrile (107-13-1,25014-41-9) → ethyl 2-(2-cyanoethyl)-3-oxobutanoate (10444-33-4)

Guidance literature:

With potassium phosphate; 1-butyl-3-methylimidazolium chloride; at 20 ℃; for 2h;

DOI:10.1039/c5nj01225b

Reference yield: 17.0%

ethyl acetoacetate (141-97-9) + acrylonitrile (107-13-1,25014-41-9) → ethyl 2-(2-cyanoethyl)-3-oxobutanoate (10444-33-4) + 2,2-bis-(2-cyano-ethyl)-acetoacetic acid ethyl ester (1112-25-0)

Guidance literature:

With dmap; In water; at 20 ℃; for 43h;

DOI:10.1016/j.tetlet.2009.04.025

Reference yield: 16.0%

ethyl acetoacetate (141-97-9) + acrylonitrile (107-13-1,25014-41-9) → ethyl 2-(2-cyanoethyl)-3-oxobutanoate (10444-33-4) + 3-carboethoxy-6-cyano-4-(carboethoxymethyl)-2,4-dimethyl-5,6-dihydropyran

Guidance literature:

With iron pentacarbonyl; bromine; at 120 - 130 ℃;

DOI:10.1007/BF00948848

upstream raw materials:

3-Chloropropionitrile

ethyl acetoacetate

acrylonitrile

3-iodopropanenitrile

Downstream raw materials:

4-cyano-2-((E)-4-nitro-phenylhydrazono)-butyric acid ethyl ester

ethyl 5-oxohexanoate

4-cyano-2-((E)-phenylhydrazono)-butyric acid ethyl ester

δ-caprolactam

Refernces

• 1、 Sawant, Anand D.,Jagadale, Suryabala D.,Desai, Uday V.,Salunkhe, Manikrao M.. "Potassium phosphate-ionic liquid mediated selective mono-Michael addition". . p. 6726 - 6729. Retrieved 2015.
• 2、 Markisz,J.A.,Gettler,J.D.. "-". . p. 1965 - 1979. Retrieved 1969.
• 3、 Vil, Vera A.,Gomes, Gabriel Dos Passos,Ekimova, Maria V.,Lyssenko, Konstantin A.,Syroeshkin, Mikhail A.,Nikishin, Gennady I.,Alabugin, Igor V.,Terent'Ev, Alexander O.. "Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF3-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones". . p. 13427 - 13445. Retrieved 2018/11/02.