(E)-Methyl 3-cyano-2-propenoate

Base Information

• Chemical Name: (E)-Methyl 3-cyano-2-propenoate
• CAS No.: 925-56-4
• Molecular Formula: C5H5NO2
• Molecular Weight: 111.0987
• Nikkaji Number: J2.228.559I,J202.847F
• Mol file: 925-56-4.mol

Synonyms:(E)-Methyl 3-cyano-2-propenoate;925-56-4;Methyl 3-cyanoacrylate;44653-08-9;Methyl3-cyanoacrylate;methyl-3-cyanoacrylate;(e)-methyl 3-cyanoacrylate;AMY6967;(E)-3-Cyanoacrylic acid methyl ester;AKOS022180876;METHYL (2E)-3-CYANOPROP-2-ENOATE;EN300-3612095

Chemical Property of (E)-Methyl 3-cyano-2-propenoate

Chemical Property:

• Vapor Pressure: 0.551mmHg at 25°C
• Boiling Point: 190.1°C at 760 mmHg
• Flash Point: 76.4°C
• PSA: 50.09000
• Density: 1.094g/cm³
• LogP: 0.23918
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 111.032028402
• Heavy Atom Count: 8
• Complexity: 151

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CC#N
• Isomeric SMILES: COC(=O)/C=C/C#N

Technology Process of (E)-Methyl 3-cyano-2-propenoate

There total 23 articles about (E)-Methyl 3-cyano-2-propenoate 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: 79.0%

(E)-4-amino-4-oxo-2-butenoic acid methyl ester (6971-10-4) → (E)-methyl 3-cyanoacrylate (925-56-4)

Guidance literature:

With trichlorophosphate; In pyridine; 1) 0 deg C, 1 h, 2) r.t., 30 min;

DOI:10.1007/BF00807603

Reference yield:

acrylonitrile (107-13-1,25014-41-9) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → cis-3-cyano-acrylic acid methyl ester (925-56-4,44653-08-9,925-55-3) + (E)-methyl 3-cyanoacrylate (925-56-4)

Guidance literature:

With [1,3-bis(2,6-Me₂C₆H₄)-4,5-dihydroimidazol-](Py)2(Cl)2Ru=CHPh; In dichloromethane; at 45 ℃; for 12h;

DOI:10.1016/j.tetlet.2005.08.062

Reference yield:

acrylonitrile (107-13-1,25014-41-9) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → cis-3-cyano-acrylic acid methyl ester (925-56-4,44653-08-9,925-55-3) + (E)-methyl 3-cyanoacrylate (925-56-4)

Guidance literature:

With [1,3-bis(2,6-Me₂C₆H₄)-4,5-dihydroimidazol-](Py)2(Cl)2Ru=CHPh; In dichloromethane; at 45 ℃; for 12h;

DOI:10.1016/j.tetlet.2005.08.062

upstream raw materials:

hydrogen cyanide

potassium cyanide

propynoic acid methyl ester

methyl 2-chloroacrylate

Downstream raw materials:

3-Cyan-2-cyclohexylpropansaeure-methylester

3-Cyan-3-cyclohexylpropansaeure-methylester

(2α,3α,4α,5α)-(+/-)-3-Methyl 2-phenylmethyl 4-cyano-2-(diphenylphosphinoyl)-5-phenyl-2,3-pyrrolidinedicarboxylate

(2α,3α,4α,5β)-(+/-)-4-Methyl 2-phenylmethyl 3-cyano-2-(diphenylphosphinoyl)-5-phenyl-2,4-pyrrolidinedicarboxylate

Refernces

• 1、 Tejedor, David,Delgado-Hernández, Samuel,Colella, Lucía,García-Tellado, Fernando. "Catalytic Hydrocyanation of Activated Terminal Alkynes". supporting information. p. 15046 - 15049. Retrieved 2019/11/22.
• 2、 Zhang, Min,Moss, Robert A.,Thompson, Jack,Krogh-Jespersen, Karsten. "Evolution of structure and reactivity in a series of iconic carbenes". scheme or table. p. 843 - 850. Retrieved 2012/03/26.