Diethyl 2-(2-cyanoethyl)malonate

Base Information

• Chemical Name: Diethyl 2-(2-cyanoethyl)malonate
• CAS No.: 17216-62-5
• Molecular Formula: C10H15 N O4
• Molecular Weight: 213.233
• Hs Code.: 29269095
• European Community (EC) Number: 241-260-7
• DSSTox Substance ID: DTXSID30169210
• Nikkaji Number: J208.272A
• Wikidata: Q72469238
• Mol file: 17216-62-5.mol

Synonyms:Diethyl 2-(2-cyanoethyl)malonate;17216-62-5;Diethyl (2-cyanoethyl)malonate;diethyl 2-(2-cyanoethyl)propanedioate;1,3-diethyl 2-(2-cyanoethyl)propanedioate;Propanedioic acid, (2-cyanoethyl)-, diethyl ester;Diethyl 2-(2-cyanoethyl)-malonate;EINECS 241-260-7;2-Cyanoethylmalonic acid diethylester;MFCD00001966;DIETHYL2-(2-CYANOETHYL)MALONATE;diethyl 2-(2-cyanoethyl)propane-1,3-dioate;Diethyl 2-cyanoethylmalonate;4,4-Dicarbethoxybutyronitrile;Diethyl 2-(cyanoethyl)malonate;Diethyl=(2-cyanoethyl)malonate;SCHEMBL7055826;DTXSID30169210;diethyl 2-(2-cyanoethyl) malonate;STR04489;2-cyanoethylmalonic acid diethyl ester;AKOS002685527;CS-W014973;Diethyl 2-(2-cyanoethyl)malonate, 96%;(2-Cyanoethyl)malonic Acid Diethyl Ester;2-(2-Cyanoethyl)malonic acid diethylester;2-(2-Cyanoethyl)malonic acid diethyl ester;A3792;FT-0604621;A26202;C-8750;EN300-211171;H11947;F8881-5383;3-Cyano-2-methylpyridine;3-Pyridinecarbonitrile, 2-methyl-

Chemical Property of Diethyl 2-(2-cyanoethyl)malonate

Chemical Property:

• Appearance/Colour: CLEAR COLORLESS TO LIGHT YELLOW LIQUID
• Vapor Pressure: 0.00238mmHg at 25°C
• Refractive Index: n20/D 1.436(lit.)
• Boiling Point: 115-118at2mmHg
• PKA: 12.15±0.59(Predicted)
• Flash Point: 113 ºC
• PSA: 76.39000
• Density: 1.078
• LogP: 1.03258
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 213.10010796
• Heavy Atom Count: 15
• Complexity: 248

Purity/Quality:

98% ^*data from raw suppliers

Diethyl 2-(2-cyanoethyl)malonate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of Diethyl 2-(2-cyanoethyl)malonate

There total 16 articles about Diethyl 2-(2-cyanoethyl)malonate 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: 96.0%

acrylonitrile (107-13-1,25014-41-9) + diethyl malonate (105-53-3) → diethyl 2-(2-cyanoethyl)malonate (17216-62-5)

Guidance literature:

With nickel(II) ferrite; In ethanol; water; Heating; Green chemistry;

DOI:10.1039/c6ra21160g

Reference yield: 82.0%

bromopropionitrile (2417-90-5) + diethyl malonate (105-53-3) → diethyl 2-(2-cyanoethyl)malonate (17216-62-5)

Guidance literature:

diethyl malonate; With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃;

bromopropionitrile; In tetrahydrofuran; mineral oil; at 20 ℃; for 12h;

DOI:10.1002/anie.202100641

Reference yield: 72.0%

chloroformic acid ethyl ester (541-41-3) + 5-(2-cyanoethyl)-2,2-dimethyl-1,3-dioxan-4,6-dione (90734-81-9) → diethyl 2-(2-cyanoethyl)malonate (17216-62-5)

Guidance literature:

With potassium carbonate; In acetone; for 4h; Heating;

DOI:10.1016/j.tetlet.2005.09.030

upstream raw materials:

diethyl nitromalonate

acrylonitrile

diethyl ether

sodium ethanolate

Downstream raw materials:

diethyl (2-cyanoethyl)<(3,5-dimethoxyphenyl)acetyl>malonate

4-cyano-2-(ethoxycarbonyl)-2-methylbutanoic acid ethyl ester

diethyl 2-benzyl-2-(2-cyanoethyl)malonate

diethyl 2-(2-cyanoethyl)-2-ethylmalonate

Refernces

• 1、 Albertson,Fillman. "-". . p. 2818. Retrieved 1949.
• 2、 Tian, Ming-Qing,Shen, Zhen-Yao,Zhao, Xuefei,Walsh, Patrick J.,Hu, Xu-Hong. "Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical". supporting information. p. 9706 - 9711. Retrieved 2021/03/19.
• 3、 DIng, Shao-Lei,Ji, Yang,Su, Yan,Li, Rui,Gu, Peiming. "Schmidt Reaction of ω-Azido Valeryl Chlorides Followed by Intermolecular Trapping of the Rearrangement Ions: Synthesis of Assoanine and Related Pyrrolophenanthridine Alkaloids". . p. 2012 - 2021. Retrieved 2019/02/14.