2-cyano-N,N-diethylacetamide

Base Information

• Chemical Name: 2-cyano-N,N-diethylacetamide
• CAS No.: 26391-06-0
• Molecular Formula: C7H12N2O
• Molecular Weight: 140.185
• Hs Code.: 2926909090
• UNII: K7FKS72PYE
• DSSTox Substance ID: DTXSID70397378
• Nikkaji Number: J2.792.372K
• Wikidata: Q27121177
• Metabolomics Workbench ID: 56963
• Mol file: 26391-06-0.mol

Synonyms:2-cyano-N,N-diethylacetamide;26391-06-0;N,N-diethylcyanoacetamide;N,N-Diethyl-2-cyanoacetamide;Acetamide, 2-cyano-N,N-diethyl-;2-Cyano-N,N-diethyl-acetamide;K7FKS72PYE;N,N-diethyl-cyanoacetamide;N,N-diethylaminocyanoacetamide;MFCD01332383;EC 607-929-6;UNII-K7FKS72PYE;N,N-diethyl cyanoacetamide;N,N-diethyl cyano acetamide;2-cyanoacetic acid diethylamide;N,N Diethyl-2-cyano acetamide;N,N'-Diethyl-2-cyanoacetamide;SCHEMBL1405183;2-cyano-N,N-diethyl-ethanamide;Acetamida, 2-ciano-n,n-dietil-;CHEBI:48386;N1,N1-diethyl-2-cyanoacetamide;AMY3916;DTXSID70397378;RYSHIRFTLKZVIH-UHFFFAOYSA-N;HMS1747E15;BCP29944;STK502146;AKOS000270706;N,N-Diethyl-2-cyanoacetoamide, 97%;AC-1753;CS-O-14924;CS-O-31469;DS-12505;SY008120;BB 0240856;C2822;CS-0112885;FT-0612166;FT-0655253;EN300-08341;F11682;A818419;J-509222;Q27121177;Z56944504

Chemical Property of 2-cyano-N,N-diethylacetamide

Chemical Property:

• Appearance/Colour: Yellow to brown liquid
• Vapor Pressure: 0.0176mmHg at 25°C
• Melting Point: 121 °C
• Refractive Index: 1.45
• Boiling Point: 254.1 °C at 760 mmHg
• PKA: 4.53±0.10(Predicted)
• Flash Point: 107.5 °C
• PSA: 44.10000
• Density: 0.988 g/cm³
• LogP: 0.76848
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform, Ethyl Acetate, Tetrahydrofuran, Methanol
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 140.094963011
• Heavy Atom Count: 10
• Complexity: 152

Purity/Quality:

99% ^*data from raw suppliers

N,N-Diethylcyanoacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)CC#N
• Uses: N,N-Diethyl-2-cyanoacetoamide can be used:To prepare N,N-diethyl 2-cyano-2-fluoro-2-phenylthioacetoamide, which is further used in the synthesis of various cyanofluoroamides.In the synthesis of entacapone, a catechol-O-methyltransferase inhibitor by reacting with 3,4-dihydroxy-5-nitrobenzaldehyde.As a building block in the synthesis of fluorophores, applicable as endoplasmic reticulum probes.

Technology Process of 2-cyano-N,N-diethylacetamide

There total 7 articles about 2-cyano-N,N-diethylacetamide 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: 97.0%

diethylamine (109-89-7) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-N,N-diethylacetamide (26391-06-0)

Guidance literature:

diethylamine; With n-hexyllithium; In tetrahydrofuran; hexanes; at -30 ℃; for 1.5h;

ethyl 2-cyanoacetate; In tetrahydrofuran; hexanes; at -30 - 20 ℃; for 0.5h;

Reference yield: 91.0%

3-(N,N-diethylamino)-3-oxopropanamide → 2-cyano-N,N-diethylacetamide (26391-06-0)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; at 15 - 20 ℃;

DOI:10.1080/00397910902788216

Reference yield: 89.0%

cyanoacetic acid (372-09-8) + diethylamine (109-89-7) → 2-cyano-N,N-diethylacetamide (26391-06-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; at 25 - 40 ℃;

upstream raw materials:

diethylamino-propynenitrile

diethylamine

ethyl 2-cyanoacetate

cyanoacetic acid

Refernces

• 1、 Berezin, Mikhail Y.,Cornelison, Lauren,Dannen, Stephanie D.,Du, Junwei,Durham, Paul,Gerasimchuk, Nikolay,Hunter, Daniel,Morley, John E.,Shahverdi, Kiana,Sudlow, Leland C.,Wood, Matthew D.,Zhou, Haiying. "New in vitro highly cytotoxic platinum and palladium cyanoximates with minimal side effects in vivo". . . Retrieved 2020/05/13.
• 2、 Davis, Owen A.,Croft, Rosemary A.,Bull, James A.. "Synthesis of diversely functionalised 2,2-disubstituted oxetanes: Fragment motifs in new chemical space". supporting information. p. 15446 - 15449. Retrieved 2015/10/20.