Ethyl 4-cyanobutanoate

Base Information

• Chemical Name: Ethyl 4-cyanobutanoate
• CAS No.: 10444-38-9
• Molecular Formula: C7H11NO2
• Molecular Weight: 141.17
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID80451157
• Nikkaji Number: J81.508J
• Mol file: 10444-38-9.mol

Synonyms:Ethyl 4-cyanobutanoate;10444-38-9;Ethyl 4-cyanobutyrate;(R)-4-cyano-3-hydrobutyric acid ethyl ester;4-Cyanobutyric acid ethyl ester;MFCD11040664;Ethyl4-cyanobutanoate;SCHEMBL9311598;DTXSID80451157;GHXXCVVSJXZBPO-UHFFFAOYSA-N;AKOS005215999;AS-42473;SY025760;CS-0151586;EN300-7313140

Chemical Property of Ethyl 4-cyanobutanoate

Chemical Property:

• Boiling Point: 242-247 °C
• PSA: 50.09000
• Density: 1.001±0.06 g/cm3(Predicted)
• LogP: 1.24338
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 141.078978594
• Heavy Atom Count: 10
• Complexity: 145

Purity/Quality:

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

Ethyl4-Cyanobutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCCC#N

Technology Process of Ethyl 4-cyanobutanoate

There total 25 articles about Ethyl 4-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: 99.0%

4-cyano-2-(ethoxycarbonyl)butanoic acid (1094201-37-2) → ethyl 4-cyanobutyrate (10444-38-9)

Guidance literature:

With 1H-imidazole; In neat (no solvent); at 125 ℃; for 0.0666667h; Microwave irradiation;

DOI:10.1016/j.tet.2015.09.012

Reference yield: 93.0%

P-toluenesulfonyl cyanide (19158-51-1) + 4-(prop-2-ene-1-sulfonyl)-butyric acid ethyl ester → ethyl 4-cyanobutyrate (10444-38-9) + 1-methyl-4-(prop-2-ene-1-sulfonyl)benzene (3112-87-6)

Guidance literature:

With 1,1'-azobis(1-cyanocyclohexanenitrile); In chlorobenzene; at 110 ℃;

DOI:10.1002/1521-3773(20020902)41:17<3265::AID-ANIE3265>3.0.CO;2-X

Reference yield: 92.0%

diethyl 2-cyanoglutarate (7251-97-0) → ethyl 4-cyanobutyrate (10444-38-9)

Guidance literature:

With lithium chloride; In water; dimethyl sulfoxide; at 140 ℃; for 4h; Inert atmosphere;

DOI:10.1002/ejoc.200900009

upstream raw materials:

diethyl 2-cyanoglutarate

ethyl 3-hydroxypropanoate

sodium cyanoacetic acid ethyl ester

diethyl 2-(2-cyanoethyl)malonate

Downstream raw materials:

4-azaspiro[2.5]octan-5-one

methyl 4-cyanobutanoate

N-(benzyloxy)-4-cyano-N-methylbutanamide

N-(benzyloxy)-N-methyl-4-(1H-tetrazol-5-yl)butanamide

Refernces

• 1、 Murai,S. et al.. "-". . p. 2104 - 2105. Retrieved 1964.
• 2、 -. "NOVEL GLYCINE TRANSPORT INHIBITORS FOR THE TREATMENT OF PAIN". Page/Page column 49. . Retrieved 2018/08/12.
• 3、 -. "MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS". Paragraph 00308; 00310. . Retrieved 2017/09/05.