Ethyl 2-cyanohexanoate

Base Information

• Chemical Name: Ethyl 2-cyanohexanoate
• CAS No.: 7391-39-1
• Molecular Formula: C9H15 N O2
• Molecular Weight: 169.224
• Hs Code.: 2926909090
• European Community (EC) Number: 230-978-6
• NSC Number: 67981
• DSSTox Substance ID: DTXSID201290050
• Nikkaji Number: J122.034I
• Mol file: 7391-39-1.mol

Synonyms:Ethyl 2-cyanohexanoate;7391-39-1;Hexanoic acid,2-cyano-, ethyl ester;Hexanoic acid, 2-cyano-, ethyl ester;EINECS 230-978-6;AI3-04910;2-cyano-hexanoic acid ethyl ester;ethyl 2-butylcyanoacetate;SCHEMBL9562158;2-Cyanohexanoic acid ethyl ester;DTXSID201290050;AMY25172;ETHYL ALPHA-BUTYLCYANOACETATE;NSC67981;NSC 67981;NSC-67981;AKOS006273577;AS-76904;FT-0656766;D93234

Chemical Property of Ethyl 2-cyanohexanoate

Chemical Property:

• Vapor Pressure: 0.114mmHg at 25°C
• Refractive Index: 1.4248
• Boiling Point: 220.3°C at 760 mmHg
• Flash Point: 93.5°C
• PSA: 50.09000
• Density: 0.97g/cm³
• LogP: 1.87948
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 169.110278721
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

99% ^*data from raw suppliers

ETHYL 2-CYANOHEXANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C#N)C(=O)OCC

Technology Process of Ethyl 2-cyanohexanoate

There total 12 articles about Ethyl 2-cyanohexanoate 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: 89.5%

1-bromo-butane (109-65-9) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanohexanoate (7391-39-1)

Guidance literature:

With potassium carbonate; In ethanol; water; at 60 ℃; for 8h; regioselective reaction;

DOI:10.1039/c5ra21597h

Reference yield: 81.0%

hexanenitrile (628-73-9) + Diethyl carbonate (105-58-8,76619-83-5) → ethyl 2-cyanohexanoate (7391-39-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; 1.) -78 deg C, 3O min, then 30 min, 2.) -78 deg C, 2.25 h;

DOI:10.1021/jo00076a017

Reference yield: 71.0%

1-iodo-butane (542-69-8) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyanohexanoate (7391-39-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; for 25h; Ambient temperature;

DOI:10.1016/S0040-4039(97)10063-6

upstream raw materials:

butyraldehyde

ethyl 2-cyanoacetate

1-bromo-butane

1-iodo-butane

Downstream raw materials:

2-cyano-hexanoic acid hydrazide

2-Ethoxycarbonimidoyl-2-fluoro-hexanoic acid ethyl ester

4-n-Butyl-5-amino-isoxazolin-3-on

2-Cyano-2-fluoro-hexanoic acid ethyl ester

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、 Shang, Rui,Huang, Zheng,Xiao, Xiao,Lu, Xi,Fu, Yao,Liu, Lei. "β-aryl nitrile construction via palladium-catalyzed decarboxylative benzylation of α-cyano aliphatic carboxylate salts". supporting information. p. 2465 - 2472,8. Retrieved 2020/08/31.