Ethyl 3-benzoylacrylate

Base Information

• Chemical Name: Ethyl 3-benzoylacrylate
• CAS No.: 17450-56-5
• Molecular Formula: C₁₂H₁₂O₃
• Molecular Weight: 204.225
• Hs Code.: 29183000
• European Community (EC) Number: 408-040-4,438-510-4,604-780-9,621-286-9
• Nikkaji Number: J134.886H,J208.122I
• Wikidata: Q76305537
• ChEMBL ID: CHEMBL4063314
• Mol file: 17450-56-5.mol

Synonyms:Ethyl 3-benzoylacrylate;17450-56-5;15121-89-8;ethyl 4-oxo-4-phenylbut-2-enoate;(E)-Ethyl 4-oxo-4-phenylbut-2-enoate;ethyl (E)-4-oxo-4-phenylbut-2-enoate;Ethyl trans-3-Benzoylacrylate;trans-3-Benzoylacrylic Acid Ethyl Ester;E-ethyl-4-oxo-4-phenylcrotonate;2-Butenoic acid, 4-oxo-4-phenyl-, ethyl ester;MFCD00011533;AI3-10548;EC 408-040-4;ETHYL-3-BENZOYLACRYLATE;ethyl (2E)-4-oxo-4-phenylbut-2-enoate;Ethyl=3-benzoylacrylate;E-ethyl-3-benzoyl-acrylate;Ethyl(E)-3-benzoylacrylate;trans-ethyl 3-benzoylacrylate;ethyl trans-beta-benzoylacrylate;SCHEMBL3371348;trans-ethyl beta-benzoylacrylate;CHEMBL4063314;2-Butenoic acid, 4-oxo-4-phenyl-, ethyl ester, (2E)-;AKOS005100232;(E)-Ethyl4-oxo-4-phenylbut-2-enoate;CS-W015409;(e)-ethyl-4-oxo-4-phenyl-2-butenoate;AS-66531;B1233;CS-0166778;Ethyl (2E)-4-oxo-4-phenyl-2-butenoate #;Ethyl 3-benzoylacrylate, predominantly trans;7N-720;D88769;Ethyl 3-benzoylacrylate, technical grade, 92%;J-520854;J-640273;J-800265;4-OXO-4-PHENYL-BUT-2-ENOIC ACID ETHYL ESTER

Chemical Property of Ethyl 3-benzoylacrylate

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 0.000839mmHg at 25°C
• Melting Point: 32 °C
• Refractive Index: 1.542-1.546
• Boiling Point: 305.1 °C at 760 mmHg
• Flash Point: 132.3 °C
• PSA: 43.37000
• Density: 1.109 g/cm³
• LogP: 1.98860
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 204.078644241
• Heavy Atom Count: 15
• Complexity: 250

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 3-benzoylacrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C=CC(=O)C1=CC=CC=C1
• Isomeric SMILES: CCOC(=O)/C=C/C(=O)C1=CC=CC=C1
• Uses: Ethyl 3-benzoylacrylate is an impurity of Enalapril (E555250), an?antihypertensive and an angiotensin-converting enzyme (ACE) inhibitor.

Technology Process of Ethyl 3-benzoylacrylate

There total 21 articles about Ethyl 3-benzoylacrylate 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: 88.0%

carbon monoxide (201230-82-2) + Phenyl triflate (17763-67-6) + ethyl acrylate (140-88-5,9003-32-1) → ethyl 3-benzoyl acrylate (15121-89-8,20908-27-4,17450-56-5)

Guidance literature:

With palladium diacetate; caesium carbonate; In water; at 35 - 95 ℃; under 3750.38 Torr; Schlenk technique; Inert atmosphere;

DOI:10.1039/c8cc00324f

Reference yield: 81.0%

1-phenyl-2-hydroxyethanone (582-24-1) + 2,3-dimethyl-buta-1,3-diene (513-81-5) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl 3-benzoyl acrylate (15121-89-8,20908-27-4,17450-56-5)

Guidance literature:

With sodium acetate; In toluene; for 6h; Reflux;

DOI:10.1016/j.tetlet.2010.10.121

Reference yield: 76.0%

(E)-4-Hydroxy-4-phenyl-but-2-enoic acid ethyl ester → ethyl 3-benzoyl acrylate (15121-89-8,20908-27-4,17450-56-5)

Guidance literature:

With 3,6-bis(triphenylphosphonium)cyclohexene dichromate; In acetonitrile; for 2h; Heating;

DOI:10.1080/10426500600634715

upstream raw materials:

ethanol

3-benzoylacrylic acid

4,4-Dimethoxy-4-phenyl-crotonsaeure-aethylester

4-phenyl-2-hydroxy-4-oxobutyric acid ethyl ester

Downstream raw materials:

3-benzylamino-4-oxo-4-phenyl-butyric acid ethyl ester

phenacyl-succinic acid

3-benzoylacrylic acid

2-imino-5-(2-phenyl-2-oxoethyl)-4-oxo-1,3-thiazolidine

Refernces

• 1、 Chai, Guo-Li,Sun, A-Qiang,Zhai, Dong,Wang, Juan,Deng, Wei-Qiao,Wong, Henry N.C.,Chang, Junbiao. "Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones". supporting information. p. 5040 - 5045. Retrieved 2019/07/03.
• 2、 Wang, Shasha,Hu, Lijuan,Cheng, Suyan,Wang, Lanzhi. "Synthesis of 1,5-benzodiazepine derivatives using p-toluenesulfonic acid as catalyst". . p. 419 - 424. Retrieved 2015/01/30.