Methyl 3-(4-methoxyphenyl)propiolate

Base Information

• Chemical Name: Methyl 3-(4-methoxyphenyl)propiolate
• CAS No.: 7515-17-5
• Molecular Formula: C11H10O3
• Molecular Weight: 190.199
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID20466482
• Nikkaji Number: J2.152.436K
• Wikidata: Q82293054
• Mol file: 7515-17-5.mol

Synonyms:Methyl 3-(4-methoxyphenyl)propiolate;7515-17-5;Methyl 3-(4-methoxyphenyl)prop-2-ynoate;methyl3-(4-methoxyphenyl)propiolate;SCHEMBL17845127;DTXSID20466482;MFCD13191991;methyl 3-(4-methoxyphenyl)propynoate;AKOS013859695;AS-62609;CS-0150428;(4-Methoxy-phenyl)-propynoic acid methyl ester;EN300-743492;F11025

Chemical Property of Methyl 3-(4-methoxyphenyl)propiolate

Chemical Property:

• Melting Point: 45-46 °C
• Boiling Point: 290.7±23.0 °C(Predicted)
• PSA: 35.53000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 1.21970
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 190.062994177
• Heavy Atom Count: 14
• Complexity: 250

Purity/Quality:

99.99%HPLC ^*data from raw suppliers

(4-Methoxy-phenyl)-propynoicacidmethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C#CC(=O)OC

Technology Process of Methyl 3-(4-methoxyphenyl)propiolate

There total 24 articles about Methyl 3-(4-methoxyphenyl)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: 95.0%

methyl chloroformate (79-22-1) + 4-methoxyphenylacetylen (768-60-5) → methyl 3-(4-methoxyphenyl)propynoate (7515-17-5)

Guidance literature:

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

methyl chloroformate; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/ol4021095

Reference yield: 92.0%

methyl 3-(4-methoxybenzoyl)acetate (22027-50-5) → methyl 3-(4-methoxyphenyl)propynoate (7515-17-5)

Guidance literature:

methyl 3-(4-methoxybenzoyl)acetate; With lithium hexamethyldisilazane; In tetrahydrofuran; ethylbenzene; at -70 ℃; for 0.5h; Inert atmosphere;

With diethyl chlorophosphate; In tetrahydrofuran; ethylbenzene; at -78 - 20 ℃; for 0.5h; Inert atmosphere;

With lithium hexamethyldisilazane; In tetrahydrofuran; ethylbenzene; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1139/cjc-2016-0181

Reference yield: 91.0%

carbon dioxide (124-38-9,18923-20-1) + (4-methoxyphenylethynyl)trimethylsilane (3989-14-8) + methyl iodide (74-88-4) → methyl 3-(4-methoxyphenyl)propynoate (7515-17-5)

Guidance literature:

carbon dioxide; With cesium fluoride; In N,N-dimethyl-formamide; at 120 ℃; Inert atmosphere;

(4-methoxyphenylethynyl)trimethylsilane; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c01171

upstream raw materials:

methanol

3-(4-Methoxyphenyl)-cyano-propiolsaeure-anhydrid

carbon monoxide

[(4-methoxyphenyl)ethynyl](phenyl)iodonium tosylate

Downstream raw materials:

5-(4-Methoxy-phenyl)-3-phenyl-isoxazole-4-carboxylic acid methyl ester

methyl 1,4,5,6-tetramethyl-3-(4'-methoxyphenyl)-bicyclo[2.2.0]hexa-2,5-diene-2-carboxylate

N,N'-((1Z,3Z)-1,4-bis(4-methoxyphenyl)buta-1,3-diene-2,3-diyl)diformamide

3-(4-methoxyphenyl)propiolamide

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、 Sugimoto, Kenji,Kosuge, Shuto,Sugita, Takae,Miura, Yuka,Tsuge, Kiyoshi,Matsuya, Yuji. "Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization". . p. 3981 - 3985. Retrieved 2021/05/26.