Ethyl 3-(4-fluorophenyl)propiolate

Base Information

• Chemical Name: Ethyl 3-(4-fluorophenyl)propiolate
• CAS No.: 1736-31-8
• Molecular Formula: C11H9 F O2
• Molecular Weight: 192.19
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID90476058
• Nikkaji Number: J1.910.899F
• Wikidata: Q82306998
• Mol file: 1736-31-8.mol

Synonyms:1736-31-8;ETHYL 3-(4-FLUOROPHENYL)PROPIOLATE;(4-FLUORO-PHENYL)-PROPYNOIC ACID ETHYL ESTER;ethyl 3-(4-fluorophenyl)prop-2-ynoate;MFCD07772986;2-Propynoic acid, 3-(4-fluorophenyl)-, ethyl ester;SCHEMBL2433672;DTXSID90476058;APRILKFBGZRBKC-UHFFFAOYSA-N;AKOS006287073;AS-42488;ETHYL3-(4-FLUOROPHENYL)PROPIOLATE;CS-0298737;EN300-743607;3-(4-fluorophenyl)-2-propynoic acid ethyl ester;A811541

Chemical Property of Ethyl 3-(4-fluorophenyl)propiolate

Chemical Property:

• Vapor Pressure: 0.0116mmHg at 25°C
• Refractive Index: 1.521
• Boiling Point: 261.3°C at 760 mmHg
• Flash Point: 108.5°C
• PSA: 26.30000
• Density: 1.17g/cm³
• LogP: 1.74030
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 192.05865769
• Heavy Atom Count: 14
• Complexity: 253

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C#CC1=CC=C(C=C1)F

Technology Process of Ethyl 3-(4-fluorophenyl)propiolate

There total 18 articles about Ethyl 3-(4-fluorophenyl)propiolate 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: 96.0%

1-ethynyl-4-fluorobenzene (766-98-3) + chloroformic acid ethyl ester (541-41-3) → ethyl 3-(4-fluorophenyl)propiolate (1736-31-8)

Guidance literature:

1-ethynyl-4-fluorobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

chloroformic acid ethyl ester; In tetrahydrofuran; hexane; at 20 ℃; for 19h; Inert atmosphere;

DOI:10.1039/c3ob42011f

Reference yield: 72.0%

4-fluoroboronic acid (1765-93-1) + propynoic acid ethyl ester (623-47-2) → ethyl 3-(4-fluorophenyl)propiolate (1736-31-8)

Guidance literature:

With copper(l) iodide; air; caesium carbonate; silver(l) oxide; In dichloromethane; at 80 ℃; for 36h;

DOI:10.1016/j.tetlet.2009.06.093

Reference yield: 67.0%

ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4) → ethyl 3-(4-fluorophenyl)propiolate (1736-31-8)

Guidance literature:

With trifluoromethylsulfonic anhydride; triethylamine; Triphenylphosphine oxide; In 1,2-dichloro-ethane; at 85 ℃; for 2h; Inert atmosphere;

upstream raw materials:

ethyl (E)-3-(4-chlorophenyl)prop-2-enoate

2,3-dibromo-3-(4-fluoro-phenyl)-propionic acid ethyl ester

ethyl 4-fluorocinnamate

4-fluoro-1-iodobenzene

Downstream raw materials:

3-(4-flurophenyl)prop-2-ynoic acid

methyl 3-(4-fluorophenyl)propiolate

ethyl (E)-3-(4-fluorophenyl)-3-fluoromethylsulfonyloxy-2-propenoate

1,6-dihydro-4-(4-fluoro-phenyl)-6-oxo-2-phenyl-pyridine-3-carboxylic acid ethyl ester

Refernces

• 1、 Drikermann, Denis,Kupfer, Stephan,Seifert, Fabian,Steinmetzer, Johannes,Vilotijevic, Ivan,Zi, You. "Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water". supporting information. p. 6092 - 6097. Retrieved 2021/07/21.
• 2、 Xia, Xiao-Feng,Zhao, Mingming,He, Wei,Zou, Lianghua,San, Xinxin,Wang, Dawei. "Metal-Free Oxidative [5+1] Cyclization of 1,5-Enynes for the Synthesis of Pyrazine 1-Oxide". supporting information. p. 3621 - 3626. Retrieved 2020/08/05.