Ethyl 3-(4-methylphenyl)prop-2-ynoate

Base Information

• Chemical Name: Ethyl 3-(4-methylphenyl)prop-2-ynoate
• CAS No.: 52188-06-4
• Molecular Formula: C12H12O2
• Molecular Weight: 188.226
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID30502204
• Nikkaji Number: J497.690H
• Wikidata: Q82355046
• Mol file: 52188-06-4.mol

Synonyms:52188-06-4;ETHYL 3-(4-METHYLPHENYL)PROP-2-YNOATE;Ethyl 3-(p-tolyl)propiolate;P-TOLYL-PROPYNOIC ACID ETHYL ESTER;OZAGRELIMPURITYII;OZAGREL IMPURITY II;DTXSID30502204;MFCD07772989;AKOS006287304;CS-0347733;EN300-743588

Chemical Property of Ethyl 3-(4-methylphenyl)prop-2-ynoate

Chemical Property:

• Boiling Point: 162-167 °C(Press: 20 Torr)
• PSA: 26.30000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 1.90960
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 188.083729621
• Heavy Atom Count: 14
• Complexity: 248

Purity/Quality:

97% ^*data from raw suppliers

P-Tolyl-propynoicacidethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Ethyl 3-(4-methylphenyl)prop-2-ynoate

There total 29 articles about Ethyl 3-(4-methylphenyl)prop-2-ynoate 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%

4-tolyl iodide (624-31-7) + propynoic acid ethyl ester (623-47-2) → ethyl 3-(4-methylphenyl)prop-2-ynoate (52188-06-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; In tetrahydrofuran; for 24h; Inert atmosphere; Heating;

DOI:10.1021/acs.orglett.9b00148

Reference yield: 97.0%

chloroformic acid ethyl ester (541-41-3) + 4-n-methylphenylacetylene (766-97-2) → ethyl 3-(4-methylphenyl)prop-2-ynoate (52188-06-4)

Guidance literature:

4-n-methylphenylacetylene; With n-butyllithium; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 1h; Inert atmosphere;

chloroformic acid ethyl ester; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/jp5078246

Reference yield: 89.0%

3-(4-methylphenyl)prop-2-ynoic acid (2227-58-9) + ethyl iodide (75-03-6) → ethyl 3-(4-methylphenyl)prop-2-ynoate (52188-06-4)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;

upstream raw materials:

ethanol

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

4-tolyl iodide

ethyl (tributylstannyl)propiolate

Downstream raw materials:

2-(4-morpholin-4-yl-phenyl)-6-p-tolyl-pyran-4-one

Dimethyloxosulfonium-3-ethoxycarbonyl-2-(p-tolyl)-allylid

2-amino-6-p-tolyl-[1,3]thiazin-4-one

7,10-Dimethyl-9-p-tolyl-fluoranthene-8-carboxylic acid ethyl ester

Refernces

• 1、 Cocoletzi-Xochitiotzi, Ana Patricia,Hernández-Hernández, Miguel,Medina-Mercado, Ignacio,Jiménez-Martínez, Williams De Jesús,Mastranzo, Virginia Maricela,Porcel, Susana. "Gold-catalyzed partial hydrogenation of activated alkynes mediated by triphenylphosphine". supporting information. p. 2379 - 2386. Retrieved 2020/08/19.
• 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.