Ethyl 3-phenylprop-2-enoate

Base Information

• Chemical Name: Ethyl 3-phenylprop-2-enoate
• CAS No.: 103-36-6
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID9022520
• Wikidata: Q105138131
• ChEMBL ID: CHEMBL3182745
• Mol file: 103-36-6.mol

Synonyms:Ethyl 3-phenylprop-2-enoate;MFCD00009189;CHEMBL3182745;Cinnamic acid, ethyl ester (6CI,7CI,8CI);3-Phenyl-2-propenoic acid ethyl ester;AKOS025243177;SY005492;FT-0623830;FT-0668209;FT-0693346

Chemical Property of Ethyl 3-phenylprop-2-enoate

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 0.00729mmHg at 25°C
• Melting Point: 6-8 °C(lit.)
• Refractive Index: n20/D 1.558(lit.)
• Boiling Point: 269.3 °C at 760 mmHg
• Flash Point: 148.6 °C
• PSA: 26.30000
• Density: 1.055 g/cm³
• LogP: 2.26290
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility.: insoluble
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 176.083729621
• Heavy Atom Count: 13
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

Ethyl cinnamate ^*data from reagent suppliers

Safty Information:

• Statements: 20-22
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC=CC=C1
• Description: Ethyl cinnamate is the ester of cinnamic acid and ethanol, and is typically found in the essential oil of cinnamon. It is noteworthy that pure ethyl cinnamate has an aroma of cinnamon, complicated by balsamic and red fruit nuances,all of which can be characteristic of a fine Nebbiolo wine's aromatics.
• Uses: Ethyl cinnamate is used in medical intermediate, as a pharmaceutical intermediate and in organic synthesis.

Technology Process of Ethyl 3-phenylprop-2-enoate

There total 196 articles about Ethyl 3-phenylprop-2-enoate 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: 95.0%

4,4'-dimethylbenzoin (1218-89-9) → ethyl 3-phenyl-2-propenoate (103-36-6) + 1,2-di(4-methylphenyl)-1,2-ethanedione (3457-48-5)

Guidance literature:

With 2,6-dimethylpyridine; 2,3-dibromo-3-phenyl-propionic acid ethyl ester; triphenylantimony dibromide; In chloroform-d1; at 70 ℃; for 72h;

DOI:10.1246/cl.1985.1577

Reference yield: 68.0%

ethanol (64-17-5) + Cinnamic acid (621-82-9) → ethyl 3-phenyl-2-propenoate (103-36-6) + cinnamic acid anhydride (538-56-7)

Guidance literature:

With magnesium chloride; at 40 ℃; for 24h;

DOI:10.1055/s-2007-990812

Reference yield: 48.0%

benzaldehyde (100-52-7) + ethyl acetate (141-78-6) → ethyl 3-phenyl-2-propenoate (103-36-6) + Ethyl 3-hydroxy-3-phenylpropanoate (5764-85-2)

Guidance literature:

ethyl acetate; With indium(III) chloride; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.166667h;

benzaldehyde; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/a907334e

upstream raw materials:

(E)-3-phenylpropenal

diethyl ether

aluminum ethoxide

ethanol

Downstream raw materials:

4-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester

ethyl 3-(ethoxycarbonylmethylmercapto)-3-phenylpropanoate

cinnamamide

2,4-dioxo-3,6-diphenyl-cyclohexanecarboxylic acid ethyl ester

Refernces

• 1、 Tiwari, Shraeddha,Kumar, Anil. "Unusual temperature dependence of salt effects for "on water" Wittig reaction: Hydrophobicity at the interface". . p. 4445 - 4447. Retrieved 2008.
• 2、 Cordier, Christopher J.,Spivey, Alan C.,White, Andrew J. P.,Williams, Alexander F.. "Meta -Selective C-H functionalisation of aryl boronic acids directed by a MIDA-derived boronate ester". . p. 3301 - 3306. Retrieved 2020.
• 3、 Pérez, Juana M.,Cano, Rafael,McGlacken, Gerard P.,Ramón, Diego J.. "Palladium(II) oxide impregnated on magnetite as a catalyst for the synthesis of 4-arylcoumarins: Via a Heck-arylation/cyclization process". . p. 36932 - 36941. Retrieved 2016.
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• 9、 Santos, Ana M.,Pedro, Filipe M.,Yogalekar, Ameya A.,Lucas, Isabel S.,Romao, Carlos C.,Kuehn, Fritz E.. "Oxorhenium complexes as aldehyde-olefination catalysts". . p. 6313 - 6321. Retrieved 2004.
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