Ethyl cis-(beta-cyano)acrylate

Base Information

• Chemical Name: Ethyl cis-(beta-cyano)acrylate
• CAS No.: 40594-97-6
• Molecular Formula: C₆H₇NO₂
• Molecular Weight: 125.127
• Hs Code.: 2926909090
• European Community (EC) Number: 626-020-5
• DSSTox Substance ID: DTXSID50574726
• Nikkaji Number: J807.893I
• Wikidata: Q72472987
• Mol file: 40594-97-6.mol

Synonyms:Ethyl cis-(beta-cyano)acrylate;40594-97-6;ethyl cis-beta-cyanoacrylate;ethyl (Z)-3-cyanoprop-2-enoate;Ethyl (2Z)-3-cyanoprop-2-enoate;(Z)-ethyl 3-cyanoacrylate;ethyl cis-3-cyanoacrylate;(z)-ethyl beta-cyanoacrylate;SCHEMBL600328;DTXSID50574726;Ethyl cis-( beta -cyano)acrylate;(Z)-3-cyano-acrylic acid ethyl ester;AKOS015999145;Ethyl cis-(beta-cyano)acrylate, 97%;BS-23570;CS-0356867;EN300-364793;F83775

Chemical Property of Ethyl cis-(beta-cyano)acrylate

Chemical Property:

• Vapor Pressure: 0.27mmHg at 25°C
• Refractive Index: n20/D 1.4530(lit.)
• Boiling Point: 215 °C(lit.)
• Flash Point: 225 °F
• PSA: 50.09000
• Density: 1.044 g/mL at 25 °C(lit.)
• LogP: 0.62928
• Storage Temp.: 2-8°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 125.047678466
• Heavy Atom Count: 9
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

Ethyl cis-(β-cyano)acrylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53
• Safety Statements: 26-28-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC#N
• Isomeric SMILES: CCOC(=O)/C=C\C#N
• Uses: Ethyl cis-β-cyanoacrylate behaves as a dienophile in the synthesis of indeno[2,1-a]pyrrolo[3,4-c]carbazole lactam regioisomers via Diels-Alder reaction.

Technology Process of Ethyl cis-(beta-cyano)acrylate

There total 3 articles about Ethyl cis-(beta-cyano)acrylate 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: 72.0%

maleamic acid (557-24-4) + chloroformic acid ethyl ester (541-41-3) → (Z)-3-cyanoacrylic acid ethyl ester (40594-97-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/adsc.201800734

Reference yield:

2-hydroxy-2-methylpropanenitrile (75-86-5) + propynoic acid ethyl ester (623-47-2) → 3-ethoxycarbonylacrylonitrile (3307-88-8) + (Z)-3-cyanoacrylic acid ethyl ester (40594-97-6)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at 20 ℃; for 1h; Solvent; Overall yield = 100 percent;

DOI:10.1002/chem.201903402

Reference yield:

→ (Z)-3-cyanoacrylic acid ethyl ester (40594-97-6)

Guidance literature:

DOI:10.1021/jo01060a002

upstream raw materials:

maleamic acid

chloroformic acid ethyl ester

2-hydroxy-2-methylpropanenitrile

propynoic acid ethyl ester

Refernces

• 1、 Choi, Jun-Ho,Park, Cheol-Min. "Three-Component Synthesis of Quinolines Based on Radical Cascade Visible-Light Photoredox Catalysis". supporting information. p. 3553 - 3562. Retrieved 2018/09/22.