Ethyl 4-chlorocinnamate

Base Information

• Chemical Name: Ethyl 4-chlorocinnamate
• CAS No.: 6048-06-2
• Molecular Formula: C11H11ClO2
• Molecular Weight: 210.66
• European Community (EC) Number: 889-352-1
• DSSTox Substance ID: DTXSID001032094
• Nikkaji Number: J586.231K,J324.966B
• Wikidata: Q76305685
• ChEMBL ID: CHEMBL2285935
• Mol file: 6048-06-2.mol

Synonyms:Ethyl 4-chlorocinnamate;24393-52-0;6048-06-2;4-Chlorocinnamic acid ethyl ester;Ethyl 3-(4-chlorophenyl)acrylate;2-Propenoic acid, 3-(4-chlorophenyl)-, ethyl ester;ethyl (E)-3-(4-chlorophenyl)prop-2-enoate;(E)-ETHYL 3-(4-CHLOROPHENYL)ACRYLATE;Ethyl p-chlorocinnamate;ethyl (2E)-3-(4-chlorophenyl)prop-2-enoate;3-(4-Chlorophenyl)-2-propenoic acid ethyl ester;Cinnamic acid, 4-chloro-, ethyl ester;Ethyl (E)-3-(4-chlorophenyl)acrylate;BRN 2046428;SCHEMBL321285;Ethyl 4-chloro-trans-cinnamate;CHEMBL2285935;Ethyl3-(4-chlorophenyl)acrylate;DTXSID001032094;ZAA39352;MFCD00045213;AKOS003622988;4-Chlorobenzeneacrylic acid ethyl ester;Cinnamic acid, p-chloro-, ethyl ester;GS-6056;trans-4-chlorocinnamic acid ethyl ester;AC-11305;LS-123593;EN300-1453799;Ethyl (2E)-3-(4-chlorophenyl)-2-propenoate #;(E)-3-(4-chlorophenyl)-acrylic acid ethyl ester;A817267;A856513;(E)-3-(4-chloro-phenyl)-acrylic acid ethyl ester;J-521326

Chemical Property of Ethyl 4-chlorocinnamate

Chemical Property:

• Vapor Pressure: 0.000703mmHg at 25°C
• Refractive Index: 1.562
• Boiling Point: 307.9 °C at 760 mmHg
• Flash Point: 151.9 °C
• PSA: 26.30000
• Density: 1.177 g/cm³
• LogP: 2.91630
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 210.0447573
• Heavy Atom Count: 14
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

4-Chlorocinnamicacidethylester 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC=C(C=C1)Cl
• Isomeric SMILES: CCOC(=O)/C=C/C1=CC=C(C=C1)Cl

Technology Process of Ethyl 4-chlorocinnamate

There total 21 articles about Ethyl 4-chlorocinnamate 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%

1-Chloro-4-iodobenzene (637-87-6) + ethyl acrylate (140-88-5,9003-32-1) → ethyl-p-chlorocinnamate (6048-06-2)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 120 ℃; for 3h; Schlenk technique; Green chemistry;

DOI:10.1039/c7nj04361a

Reference yield: 99.0%

diazoacetic acid ethyl ester (623-73-4) + 4-chlorobenzaldehyde (104-88-1) → ethyl-p-chlorocinnamate (6048-06-2)

Guidance literature:

With triphenylphosphine; ruthenium-salen complex; In toluene; at 60 ℃; for 3h;

DOI:10.1016/j.tetlet.2006.01.055

Reference yield: 97.0%

bromochlorobenzene (106-39-8) + ethyl acrylate (140-88-5,9003-32-1) → ethyl-p-chlorocinnamate (6048-06-2)

Guidance literature:

With potassium phosphate; [((ferrocenyl)(C(CH₃)N(C₆H₄)CH₃))PdCl(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)]; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 140 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tet.2010.04.040

upstream raw materials:

p-chlorocinnamic acid

ethanol

(4-Chlorophenylmethylene)triphenylphosphorane

ethyl bromoacetate

Downstream raw materials:

2,3-dibromo-4'-chlorocinnamic acid ethyl ester

3-(4-Chloro-phenyl)-4-methyl-pent-3-enoic acid ethyl ester

4-chlorocinnamyl benzoate

3-(4-chlorophenyl)propanoic acid

Refernces

• 1、 Chen, Yi,Gao, Lu,Song, Xuanyi,Song, Zhenlei. "Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization to Form Functionalized Hexahydropyrido[3,4- b]Indole". supporting information. p. 124 - 128. Retrieved 2021/01/13.
• 2、 Kan, Jian,Li, Chao-Jun,Li, Chen-Chen,Li, Jianbin,Lv, Leiyang,Qiu, Zihang. "Synergistic Relay Reactions To Achieve Redox-Neutral α-Alkylations of Olefinic Alcohols with Ruthenium(II) Catalysis". supporting information. p. 4544 - 4549. Retrieved 2020/02/04.