O-Tolyl-propynoic acid ethyl ester

Base Information

• Chemical Name: O-Tolyl-propynoic acid ethyl ester
• CAS No.: 58686-71-8
• Molecular Formula: C12H12O2
• Molecular Weight: 188.226
• DSSTox Substance ID: DTXSID00439215
• Nikkaji Number: J612.147K
• Wikidata: Q82255129
• ChEMBL ID: CHEMBL2425325
• Mol file: 58686-71-8.mol

Synonyms:58686-71-8;O-TOLYL-PROPYNOIC ACID ETHYL ESTER;Ethyl 3-(2-methylphenyl)prop-2-ynoate;O-TOLYL-PROPYNOICACIDETHYLESTER;Ethyl 3-(o-tolyl)propiolate;ethyl 2-methylphenylpropiolate;SCHEMBL9372996;CHEMBL2425325;DTXSID00439215;CWXGWDMRDPUIRJ-UHFFFAOYSA-N;MFCD07773001;AKOS006287535;CS-0347739;3-(2-Methylphenyl)propiolic acid ethyl ester;EN300-743564

Chemical Property of O-Tolyl-propynoic acid ethyl ester

Chemical Property:

• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.534
• Boiling Point: 286.428°C at 760 mmHg
• Flash Point: 136.762°C
• PSA: 26.30000
• Density: 1.076g/cm³
• 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: 256

Purity/Quality:

97% ^*data from raw suppliers

O-Tolyl-propynoicacidethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C#CC1=CC=CC=C1C

Technology Process of O-Tolyl-propynoic acid ethyl ester

There total 10 articles about O-Tolyl-propynoic acid ethyl ester 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: 98.0%

chloroformic acid ethyl ester (541-41-3) + 1,1-dibromo-2-(2-methylphenyl)ethene (104464-03-1) → ethyl 3-(2-methylphenyl)prop-2-ynoate (58686-71-8)

Guidance literature:

1,1-dibromo-2-(2-methylphenyl)ethene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h; Inert atmosphere;

chloroformic acid ethyl ester; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1246/cl.170404

Reference yield: 90.0%

indium(III) chloride + ortho-methylphenyl iodide (615-37-2) + propynoic acid ethyl ester (623-47-2) → ethyl 3-(2-methylphenyl)prop-2-ynoate (58686-71-8)

Guidance literature:

propynoic acid ethyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Inert atmosphere;

indium(III) chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.333333h; Inert atmosphere;

ortho-methylphenyl iodide; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; hexane; at 80 ℃; for 1.5h; Inert atmosphere;

DOI:10.1055/s-0033-1339110

Reference yield: 90.0%

(α-ethoxycarbonyl-α-2-methylbenzoylmethylene)triphenylphosphorane (131292-23-4) → ethyl 3-(2-methylphenyl)prop-2-ynoate (58686-71-8)

Guidance literature:

at 500 ℃; under 0.1 - 1 Torr;

upstream raw materials:

(α-ethoxycarbonyl-α-2-methylbenzoylmethylene)triphenylphosphorane

ortho-toluoyl chloride

2-Methylphenylboronic acid

propynoic acid ethyl ester

Downstream raw materials:

(Z)-ethyl 3-chloro-2-((4-oxooxetan-2-yl)methyl)-3-(o-tolyl)acrylate

Refernces

• 1、 Jiang, Huanfeng,Yan, Wuxin,Huang, Jiuzhong,Tan, Chaowei,Zhan, Lingzhi,Wu, Wanqing. "Palladium-Catalyzed Regio- and Stereoselective Sulfonylation of Aryl Propiolates with Sulfonyl Hydrazides: Access to (E)-β-Aryl Sulfonyl Acrylates". supporting information. p. 4575 - 4580. Retrieved 2019/09/16.
• 2、 Butcher, Trevor W.,Hartwig, John F.. "Enantioselective Synthesis of Tertiary Allylic Fluorides by Iridium-Catalyzed Allylic Fluoroalkylation". supporting information. p. 13125 - 13129. Retrieved 2018/09/25.