Ethyl 2-cyanobutanoate

Base Information

• Chemical Name: Ethyl 2-cyanobutanoate
• CAS No.: 1619-58-5
• Molecular Formula: C7H11NO2
• Molecular Weight: 141.17
• Hs Code.: 2926909090
• European Community (EC) Number: 630-887-5
• NSC Number: 1101
• UNII: HC5NP58RS6
• DSSTox Substance ID: DTXSID80277197
• Nikkaji Number: J818.885H
• Mol file: 1619-58-5.mol

Synonyms:ethyl 2-cyanobutanoate;1619-58-5;Butanoic acid, 2-cyano-, ethyl ester;ethyl 2-cyanobutyrate;HC5NP58RS6;NSC-1101;MFCD02258598;NSC1101;UNII-HC5NP58RS6;2-Cyanobutyric acid ethyl ester;SCHEMBL10920266;2-cyano-butyric acid ethyl ester;DTXSID80277197;NSC 1101;Butyric acid, 2-cyano-, ethyl ester;3-Bromo-2,5-Dimethylphenylboronicacid;AKOS011113241;Butyric acid, alpha-cyano-, Et ester;AB11285;CS-W022659;2-CYANOBUTYRIC ACID, ETHYL ESTER;SY005851;FT-0713448;EN300-58905;Z878447228

Chemical Property of Ethyl 2-cyanobutanoate

Chemical Property:

• Vapor Pressure: 0.304mmHg at 25°C
• Melting Point: 220-223 °C
• Refractive Index: 1.424
• Boiling Point: 201.7 °C at 760 mmHg
• Flash Point: 82.9 °C
• PSA: 50.09000
• Density: 0.998 g/cm³
• LogP: 1.09928
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 141.078978594
• Heavy Atom Count: 10
• Complexity: 156

Purity/Quality:

98% ^*data from raw suppliers

Ethyl2-Cyanobutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C#N)C(=O)OCC

Technology Process of Ethyl 2-cyanobutanoate

There total 19 articles about Ethyl 2-cyanobutanoate 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: 82.0%

ethyl iodide (75-03-6) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-butyric acid ethyl ester (1619-58-5)

Guidance literature:

ethyl 2-cyanoacetate; With sodium hydride; In tetrahydrofuran; paraffin oil; at 0 ℃; for 0.25h; Inert atmosphere;

ethyl iodide; In tetrahydrofuran; paraffin oil; at 0 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.3762/bjoc.11.98

Reference yield: 82.0%

α-ethyl-α-cyanoacetaldehyde diethyl acetal → 2-cyano-butyric acid ethyl ester (1619-58-5)

Guidance literature:

Reference yield: 70.0%

ethyl (E)-2-cyanobut-2-enoate (65221-11-6) → 2-cyano-butyric acid ethyl ester (1619-58-5)

Guidance literature:

With Bakers yeast; In water; Petroleum ether; for 24h;

DOI:10.1016/S0040-4039(98)00945-9

upstream raw materials:

sodium cyanoacetic acid ethyl ester

ethyl iodide

acetaldehyde

ethyl 2-cyanoacetate

Downstream raw materials:

2-benzyl-2-cyano-butyric acid ethyl ester

ethyl 2-cyano-2-methylbutanoate

6-amino-5-ethyl-1-methylpyrimidine-2,4(1H,3H)-dione

1-naphthalen-1-ylbutan-1-one

Refernces

• 1、 Hu, Chen,Hong, Gang,Qian, Xiaofei,Kim, Kwang Rim,Zhu, Xiaoyan,Wang, Limin. "AlCl3 catalyzed coupling of: N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon-nitrogen bond cleavage". supporting information. p. 4984 - 4991. Retrieved 2017/07/10.
• 2、 Mallia, Carl J.,Englert, Lukas,Walter, Gary C.,Baxendale, Ian R.. "Thiazole formation through a modified Gewald reaction". supporting information. p. 875 - 883. Retrieved 2015/08/24.