Methyl 3-ethynylbenzoate

Base Information

• Chemical Name: Methyl 3-ethynylbenzoate
• CAS No.: 10602-06-9
• Molecular Formula: C10H8O2
• Molecular Weight: 160.172
• Hs Code.: 2916399090
• European Community (EC) Number: 688-935-6
• DSSTox Substance ID: DTXSID30460794
• Nikkaji Number: J692.384D
• Wikidata: Q82284944
• Mol file: 10602-06-9.mol

Synonyms:Methyl 3-ethynylbenzoate;10602-06-9;3-ETHYNYL-BENZOIC ACID METHYL ESTER;3-Ethynylbenzoic acid methyl ester;MFCD08703579;Methyl3-Ethynylbenzoate;BENZOIC ACID, 3-ETHYNYL-, METHYL ESTER;SCHEMBL166803;DTXSID30460794;DDXZMLZQQWVSRX-UHFFFAOYSA-N;3-ethinylbenzoic acid methyl ester;Benzoic acid,3-ethynyl-,methyl ester;AKOS006229911;AB48503;AM85468;CS-W005738;FS-2417;SY033191;EN300-1827776;A895906

Chemical Property of Methyl 3-ethynylbenzoate

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 0.0208mmHg at 25°C
• Melting Point: 53.5-55℃
• Refractive Index: 1.537
• Boiling Point: 251.1 °C at 760 mmHg
• Flash Point: 98 °C
• PSA: 26.30000
• Density: 1.11 g/cm³
• LogP: 1.45450
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 160.052429494
• Heavy Atom Count: 12
• Complexity: 211

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl3-Ethynylbenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=CC(=C1)C#C
• Uses: Methyl 3-ethynylbenzoate is a useful research chemical.

Technology Process of Methyl 3-ethynylbenzoate

There total 13 articles about Methyl 3-ethynylbenzoate 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%

methyl 3-<(trimethylsilyl)ethynyl>benzoate (77123-59-2) → methyl 3-ethynylbenzoate (10602-06-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/acs.jmedchem.8b01512

Reference yield: 96.0%

methanol (67-56-1) + tert-butyl 3-ethynylbenzoate (914943-91-2) → methyl 3-ethynylbenzoate (10602-06-9)

Guidance literature:

tert-butyl 3-ethynylbenzoate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;

methanol; With sulfuric acid; at 65 ℃; for 20h;

Reference yield: 72.0%

3-(3-hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester (33577-97-8) → methyl 3-ethynylbenzoate (10602-06-9)

Guidance literature:

With sodium hydride; In toluene; at 110 ℃;

DOI:10.1021/jo00210a042

upstream raw materials:

3-(3-hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester

methyl 3-<(trimethylsilyl)ethynyl>benzoate

2-ethynyl-1,3-butadiene

propynoic acid methyl ester

Downstream raw materials:

3-(hydroxymethyl)ethynylbenzene

3-ethynylbenzoic acid

methyl 2-{2-[3-(methoxycarbonyl)phenyl]-1-ethynyl}-5-(trimethylsilylethynyl)-benzoate

3-[3-(2,4-diamino-pyrimidin-5-ylmethyl)-4-methoxy-phenylethynyl]-benzoic acid methyl ester

Refernces

• 1、 Cui, Shengyang,Wang, Yongjin,Wang, Yuting,Tang, Xia,Ren, Xiaomei,Zhang, Lei,Xu, Yong,Zhang, Zhang,Zhang, Zhi-Min,Lu, Xiaoyun,Ding, Ke. "Design, synthesis and biological evaluation of 3-(imidazo[1,2-a]pyrazin-3-ylethynyl)-2-methylbenzamides as potent and selective pan-tropomyosin receptor kinase (TRK) inhibitors". . p. 470 - 482. Retrieved 2019.
• 2、 -. "COMBINATION PRODUCT FOR THE TREATMENT OF CANCEROUS DISEASES". . . Retrieved 2021/12/31.
• 3、 Qiu, Sheng-Qi,Ahmad, Tanveer,Xu, Yun-He,Loh, Teck-Peng. "Palladium-Catalyzed Cascade Intramolecular Cyclization and Allylation of Enynoates with Allylic Alcohols". . p. 6729 - 6736. Retrieved 2019/06/14.