Ethyl phenylpropiolate

Base Information

• Chemical Name: Ethyl phenylpropiolate
• CAS No.: 2216-94-6
• Molecular Formula: C11H10O2
• Molecular Weight: 174.199
• Hs Code.: 29163990
• European Community (EC) Number: 218-703-8
• NSC Number: 41566
• UNII: 09CYB3Z9MR
• DSSTox Substance ID: DTXSID9074858
• Nikkaji Number: J1.803A
• Wikidata: Q26841274
• ChEMBL ID: CHEMBL1992423
• Mol file: 2216-94-6.mol

Synonyms:ethylphenylpropiolate

Chemical Property of Ethyl phenylpropiolate

Chemical Property:

• Appearance/Colour: light yellow liquid
• Vapor Pressure: 0.0094mmHg at 25°C
• Melting Point: 149-150 °C
• Refractive Index: n20/D 1.552(lit.)
• Boiling Point: 265 °C at 760 mmHg
• Flash Point: 124.9 °C
• PSA: 26.30000
• Density: 1.09 g/cm³
• LogP: 1.60120
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 225

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl Phenylpropiolate ^*data from reagent suppliers

Safty Information:

• Statements: 36/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C#CC1=CC=CC=C1
• Uses: Ethyl phenylpropiolate, is an important organic intermediate. It is also used as an intermediate in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

Technology Process of Ethyl phenylpropiolate

There total 93 articles about Ethyl phenylpropiolate 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%

iodobenzene (591-50-4) + propynoic acid ethyl ester (623-47-2) → phenylpropynoic acid ethyl ester (2216-94-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; In 1,2-dimethoxyethane; at 40 ℃; for 13h; Schlenk technique; Inert atmosphere;

DOI:10.1002/ejoc.202000823

Reference yield: 99.0%

ethanol (64-17-5) + phenylpropyolic acid (637-44-5) → phenylpropynoic acid ethyl ester (2216-94-6)

Guidance literature:

phenylpropyolic acid; With N-(methyl)-N-(p-toluenesulfonyl)ethynylamine; In dichloromethane; at 20 ℃;

ethanol; With N,N,N'N'-tetramethyl-1,3-propanediamine; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1021/acs.joc.0c00485

Reference yield: 98.0%

ethyl 3-oxo-3-phenylpropionate (94-02-0) → phenylpropynoic acid ethyl ester (2216-94-6)

Guidance literature:

With 2O*2OTf(1-); triethylamine; In 1,2-dichloro-ethane; for 1h; Heating;

DOI:10.1055/s-1989-27207

upstream raw materials:

phenylpropiolyl chloride

ethanol

rac-(2S,3R)-ethyl 2,3-dibromo-3-phenylpropanoate

chloroformic acid ethyl ester

Downstream raw materials:

β-diethylamino-cinnamic acid ethyl ester

5-benzylidene-2-thiohydantoin

2,6-diphenyl-pyran-4-one

trans-β-Benzylthiocinnamic acid

Refernces

• 1、 Lin, Ran,Lee, Ka-Ho,Poon, Ka Chun,Sung, Herman H. Y.,Williams, Ian D.,Lin, Zhenyang,Jia, Guochen. "Synthesis of rhenabenzenes from the reactions of rhenacyclobutadienes with ethoxyethyne". . p. 14885 - 14899. Retrieved 2014.
• 2、 Jozitsch,Seslawin. "-". . p. 1491. Retrieved 1910.
• 3、 G?tzinger, Alissa C.,Michaelis, Carina S.,Müller, Thomas J.J.. "3-Phenothiazinyl propiolates – Fluorescent electrophores by Sonogashira coupling of ethyl propiolate". . p. 308 - 316. Retrieved 2017.
• 4、 Bolt, Robert R. A.,Browne, Duncan L.,Howard, Joseph L.,Khan, Adam,Magri, Giuseppina,Morrill, Louis C.,Nicholson, William I.,Richards, Emma,Seastram, Alex C.. "Ball-Milling-Enabled Reactivity of Manganese Metal**". supporting information. p. 23128 - 23133. Retrieved 2021/09/20.
• 5、 Wang, Dan,Lin, Junhui,Zhu, Yannan,Huang, You. "De Novo Construction of Substituted Terephthalates via Phosphine Catalyzed Domino Benzannulation Reactions". supporting information. p. 1873 - 1877. Retrieved 2021/02/16.