alpha-Cyano-2-chloro-cis-cinnamic acid ethyl ester

Base Information

• Chemical Name: alpha-Cyano-2-chloro-cis-cinnamic acid ethyl ester
• CAS No.: 14561-93-4
• Molecular Formula: C₁₂H₁₀ClNO₂
• Molecular Weight: 235.67
• NSC Number: 172308
• Nikkaji Number: J1.245.709J
• Mol file: 14561-93-4.mol

Synonyms:CAK130452;NSC172308;AKOS002969002;NSC-172308;alpha-Cyano-2-chloro-cis-cinnamic acid ethyl ester;ethyl (2Z)-3-(2-chlorophenyl)-2-cyanoprop-2-enoate

Chemical Property of alpha-Cyano-2-chloro-cis-cinnamic acid ethyl ester

Chemical Property:

• Vapor Pressure: 1.62E-05mmHg at 25°C
• Boiling Point: 365°Cat760mmHg
• Flash Point: 174.5°C
• PSA: 50.09000
• Density: 1.249g/cm³
• LogP: 2.81008
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 235.0400063
• Heavy Atom Count: 16
• Complexity: 329

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=CC1=CC=CC=C1Cl)C#N
• Isomeric SMILES: CCOC(=O)/C(=C\C1=CC=CC=C1Cl)/C#N

Technology Process of alpha-Cyano-2-chloro-cis-cinnamic acid ethyl ester

There total 6 articles about alpha-Cyano-2-chloro-cis-cinnamic acid ethyl ester 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: 99.0%

2-chloro-benzaldehyde (89-98-5) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3-(2-chlorophenyl)-2-cyanoacrylate (24393-43-9,140241-90-3,14561-93-4)

Guidance literature:

With N-aminoethylpiperazine functionalized C₆₀ fullerene; In ethanol; at 60 ℃; for 2h;

DOI:10.1039/c5ra16011a

Reference yield: 85.0%

ethanol (64-17-5) + 2-chloro-benzaldehyde (89-98-5) + cyanoacetic acid amide (107-91-5) → ethyl 3-(2-chlorophenyl)-2-cyanoacrylate (24393-43-9,140241-90-3,14561-93-4)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; In neat (no solvent); at 80 ℃; for 12h;

DOI:10.1002/cjoc.201500420

Reference yield: 82.0%

4-methoxy-benzaldehyde (123-11-5) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3-(2-chlorophenyl)-2-cyanoacrylate (24393-43-9,140241-90-3,14561-93-4)

Guidance literature:

With Re(NCCHCO2Et)(PMe2Ph)4; In benzene; for 14h; Ambient temperature;

DOI:10.1016/S0022-328X(98)00768-2

upstream raw materials:

2-chloro-benzaldehyde

ethyl 2-cyanoacetate

4-methoxy-benzaldehyde

ethanol

Downstream raw materials:

3-(2-Chlorophenyl)succinic acid

(+/-)-(2-chloro-phenyl)-succinic acid-anhydride

5-(2-chlorophenyl)-1-phenyl-1H-pyrazole

ethyl 3-amino-1-(2-chlorophenyl)-1H-benzo[f]chromene-2-carboxylate

Refernces

• 1、 Kong, Hui,Xu, Baijie,Zhen, Jing,Liu, Siyu,Li, Keli,Ma, Pengtao,Wang, Jingping,Niu, Jingyang. "Organophosphonate-Functionalized Telluromolybdate Containing a [TeMo10O37]10-Building Block and Its Catalytic Efficiency for Knoevenagel Condensation". . p. 14872 - 14879. Retrieved 2021/10/01.
• 2、 Zhu, Hai,Xu, Gang,Du, Huimin,Zhang, Chenlu,Ma, Ning,Zhang, Wenqin. "Prolinamide functionalized polyacrylonitrile fiber with tunable linker length and surface microenvironment as efficient catalyst for Knoevenagel condensation and related multicomponent tandem reactions". . p. 217 - 229. Retrieved 2019/05/16.