M-Tolyl-propynoic acid ethyl ester

Base Information

• Chemical Name: M-Tolyl-propynoic acid ethyl ester
• CAS No.: 58686-70-7
• Molecular Formula: C12H12O2
• Molecular Weight: 188.226
• DSSTox Substance ID: DTXSID40700698
• Wikidata: Q82632144
• Mol file: 58686-70-7.mol

Synonyms:M-TOLYL-PROPYNOIC ACID ETHYL ESTER;58686-70-7;ETHYL 3-(3-METHYLPHENYL)PROP-2-YNOATE;Ethyl3-(m-tolyl)propiolate;Ethyl 3-(m-tolyl)propiolate;DTXSID40700698;MFCD07772995;AKOS006287307;EN300-743521

Chemical Property of M-Tolyl-propynoic acid ethyl ester

Chemical Property:

• PSA: 26.30000
• 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:

98%, ^*data from raw suppliers

M-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(=C1)C

Technology Process of M-Tolyl-propynoic acid ethyl ester

There total 7 articles about M-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: 85.0%

chloroformic acid ethyl ester (541-41-3) + 1-(2,2-dibromovinyl)-3-methylbenzene (97065-56-0) → ethyl 3-(m-tolyl)propiolate (58686-70-7)

Guidance literature:

1-(2,2-dibromovinyl)-3-methylbenzene; 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: 57.0%

m-tolylboronic acid (17933-03-8) + propynoic acid ethyl ester (623-47-2) → ethyl 3-(m-tolyl)propiolate (58686-70-7)

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:

chloroformic acid ethyl ester (541-41-3) + m-tolyl aldehyde (620-23-5) → ethyl 3-(m-tolyl)propiolate (58686-70-7)

Guidance literature:

m-tolyl aldehyde; With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃;

With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h;

chloroformic acid ethyl ester; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/j.ejmech.2014.11.017

upstream raw materials:

m-tolylboronic acid

propynoic acid ethyl ester

1-ethynyl-3-methyl-benzene

chloroformic acid ethyl ester

Downstream raw materials:

(Z)-ethyl 2-(bromo(m-tolyl)methylene)-4-formylbutanoate

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

ethyl m-toluoylacetate

Refernces

• 1、 Han, Zhengyu,Liu, Gang,Zhang, Xianghe,Li, Anqi,Dong, Xiu-Qin,Zhang, Xumu. "Synthesis of Chiral β-Borylated Carboxylic Esters via Nickel-Catalyzed Asymmetric Hydrogenation". supporting information. p. 3923 - 3926. Retrieved 2019/06/14.
• 2、 Liu, Gang,Han, Zhengyu,Dong, Xiu-Qin,Zhang, Xumu. "Rh-Catalyzed Asymmetric Hydrogenation of β-Substituted-β-thio-α,β-unsaturated Esters: Expeditious Access to Chiral Organic Sulfides". supporting information. p. 5636 - 5639. Retrieved 2018/09/12.