Ethyl 2-phenylacrylate

Base Information

• Chemical Name: Ethyl 2-phenylacrylate
• CAS No.: 22286-82-4
• Molecular Formula: C11H12 O2
• Molecular Weight: 176.215
• Hs Code.: 2916399090
• European Community (EC) Number: 244-892-1
• UNII: PT7338P3HC
• DSSTox Substance ID: DTXSID7066776
• Nikkaji Number: J285.474K
• Wikidata: Q72476636
• Mol file: 22286-82-4.mol

Synonyms:ETHYL 2-PHENYLACRYLATE;22286-82-4;Ethyl atropate;ethyl 2-phenylprop-2-enoate;2-Phenylacrylic Acid Ethyl Ester;Ethyl methylenephenylacetate;Benzeneacetic acid, .alpha.-methylene-, ethyl ester;PT7338P3HC;Benzeneacetic acid, alpha-methylene-, ethyl ester;EINECS 244-892-1;Ethyl altropate;ETHYL2-PHENYLACRYLATE;UNII-PT7338P3HC;SCHEMBL316956;DTXSID7066776;2-phenyl-acrylic acid ethyl ester;AKOS016001490;DS-12322;CS-0151914;ETHYL .ALPHA.-METHYLENEBENZENEACETATE;FT-0638209;EN300-67239;A878624;J-014624;Ethyl 2-phenylpropenoate

Chemical Property of Ethyl 2-phenylacrylate

Chemical Property:

• Boiling Point: 123-125°C 16mm
• PSA: 26.30000
• Density: 1.0419 g/cm3(Temp: 25 °C)
• LogP: 2.26290
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Dichloromethane, Ethyl Acetate, Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 176.083729621
• Heavy Atom Count: 13
• Complexity: 190

Purity/Quality:

99%, ^*data from raw suppliers

EthylAtropate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=C)C1=CC=CC=C1
• Uses: Intermediate in the production of Tilidine and derivatives of Tilidine.

Technology Process of Ethyl 2-phenylacrylate

There total 41 articles about Ethyl 2-phenylacrylate 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: 100.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Ethyl 2-phenylethanoate (101-97-3) → 2-phenyl-acrylic acid ethyl ester (22286-82-4)

Guidance literature:

Ethyl 2-phenylethanoate; With ethanol; sodium hydride; oxalic acid diethyl ester; In 5,5-dimethyl-1,3-cyclohexadiene; mineral oil; at 0 - 20 ℃; for 14h;

formaldehyd; In water; for 1h;

With potassium carbonate; In water; for 14h;

DOI:10.1016/j.bmc.2011.08.070

Reference yield: 98.0%

2-bromo-acrylic acid ethyl ester (5459-35-8) + iodobenzene (591-50-4) → 2-phenyl-acrylic acid ethyl ester (22286-82-4)

Guidance literature:

2-bromo-acrylic acid ethyl ester; With naphthalene; tetraethylammonium perchlorate; zinc; In N,N-dimethyl-formamide; at -20 ℃; for 1h;

iodobenzene; dichlorobis(tri-O-tolylphosphine)palladium; In N,N-dimethyl-formamide; at 70 ℃; for 3h;

DOI:10.1055/s-2001-18773

Reference yield: 95.0%

ethanol (64-17-5) + 2-phenylacrylic acid (492-38-6) → 2-phenyl-acrylic acid ethyl ester (22286-82-4)

Guidance literature:

With benzenesulfonic acid; In benzene; Heating;

DOI:10.1080/00397919708005466

upstream raw materials:

formaldehyd

2-oxo-3-phenylbutanedioic acid diethyl ester

2-chloro-2-phenyl-propionic acid ethyl ester

sodium phenoxide

Downstream raw materials:

2-(4-amino-phenyl)-acrylic acid ethyl ester

2,4-dioxo-7-phenyl-1,3,4,5,6,7-hexahydro-2H-pyrano[2,3-d]pyrimidine-7-carboxylic acid ethyl ester

Aethyl-α-phenyl-β-(9-methoxycarbonyl-9-fluorenyl)propionat

3-Methyl-4-phenyl-4,5-dihydro-isoxazole-4-carboxylic acid ethyl ester

Refernces

• 1、 Mahmood, Syed J.,Brennan, Courtney,Mahmun Hossain. "A convenient new synthesis of a Naproxen precursor". . p. 1807 - 1809. Retrieved 2002.
• 2、 Xie, Zhen-Zhen,Zheng, Yu,Tang, Kai,Guan, Jian-Ping,Yuan, Chu-Ping,Xiao, Jun-An,Xiang, Hao-Yue,Chen, Kai,Chen, Xiao-Qing,Yang, Hua. "Visible-Light-Promoted Hydroxydifluoroalkylation of Alkenes Enabled by Electron Donor–Acceptor Complex". supporting information. p. 9474 - 9479. Retrieved 2021/12/14.
• 3、 Schade, Markus,Merla, Beatrix,Lesch, Bernhard,Wagener, Markus,Timmermanns, Simone,Pletinckx, Katrien,Hertrampf, Torsten. "Highly Selective Sub-Nanomolar Cathepsin S Inhibitors by Merging Fragment Binders with Nitrile Inhibitors". supporting information. p. 11801 - 11808. Retrieved 2020/11/26.