3-(4-Methoxyphenyl)propiolic acid

Base Information

• Chemical Name: 3-(4-Methoxyphenyl)propiolic acid
• CAS No.: 2227-57-8
• Molecular Formula: C10H8 O3
• Molecular Weight: 176.172
• Hs Code.: 2918990090
• European Community (EC) Number: 875-063-8
• NSC Number: 61877
• DSSTox Substance ID: DTXSID10289546
• Nikkaji Number: J1.237.316C
• Wikidata: Q82026885
• Mol file: 2227-57-8.mol

Synonyms:2227-57-8;3-(4-Methoxyphenyl)propiolic acid;3-(4-Methoxyphenyl)-2-propynoic acid;3-(4-methoxyphenyl)prop-2-ynoic acid;(4-Methoxy-phenyl)-propynoic acid;3-(4-Methoxyphenyl)propiolicacid;NSC61877;SCHEMBL670580;IFLab1_001771;DTXSID10289546;3-(4-Methoxyphenyl)propalic acid;3-(4-methoxyphenyl)propynoic acid;3-(p-Methoxyphenyl)propiolic acid;HMS1417A11;CAA22757;MFCD00181523;NSC-61877;AKOS001630962;3-[4-(Methoxy)-phenyl]-propiolic acid;3-(4-Methoxyphenyl)-2-propynoic acid #;AS-47780;CS-0122129;EU-0039294;EN300-743493;F16131;SR-01000443415;SR-01000443415-1;Z57100824

Chemical Property of 3-(4-Methoxyphenyl)propiolic acid

Chemical Property:

• Vapor Pressure: 3.21E-05mmHg at 25°C
• Boiling Point: 340.9°C at 760 mmHg
• Flash Point: 139.1°C
• PSA: 46.53000
• Density: 1.26g/cm³
• LogP: 1.13130
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 176.047344113
• Heavy Atom Count: 13
• Complexity: 237

Purity/Quality:

99% ^*data from raw suppliers

3-(4-Methoxyphenyl)-2-propynoicAcid ^*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)O
• Uses: 3-(4-Methoxyphenyl)-2-propynoic Acid (cas# 2227-57-8) is a useful reagent for preparing bis(phenylethynyl)benzenes.

Technology Process of 3-(4-Methoxyphenyl)propiolic acid

There total 36 articles about 3-(4-Methoxyphenyl)propiolic acid 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: 98.9%

carbon dioxide (124-38-9,18923-20-1) + 4-methoxyphenylacetylen (768-60-5) → 3-(4-methoxyphenyl)propynoic acid (2227-57-8)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 15h; under 760.051 Torr; Schlenk technique;

DOI:10.1002/anie.201409103

Reference yield: 95.0%

methyl 3-(4-methoxyphenyl)propynoate (7515-17-5) → 3-(4-methoxyphenyl)propynoic acid (2227-57-8)

Guidance literature:

methyl 3-(4-methoxyphenyl)propynoate; With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20 ℃;

With hydrogenchloride; In water; ethyl acetate; at 0 ℃; for 1h; pH=4;

DOI:10.1016/j.ejmech.2010.09.003

Reference yield: 93.0%

1-(2,2-dibromovinyl)-4-methoxybenzene (60512-57-4) + carbon dioxide (124-38-9,18923-20-1) → 3-(4-methoxyphenyl)propynoic acid (2227-57-8)

Guidance literature:

1-(2,2-dibromovinyl)-4-methoxybenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1.5h;

carbon dioxide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With water; In tetrahydrofuran; hexane;

upstream raw materials:

2,3-dibromo-3-(4-methoxyphenyl)propionic acid methyl ester

2-bromo-3-(4-methoxy-phenyl)-acrylic acid

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

carbon dioxide

Downstream raw materials:

4-(4-methoxyphenyl)coumarin

1-bromo-2-(4-methoxyphenyl)acetylene

1-(iodoethynyl)-4-methoxybenzene

2-(4-methoxyphenyl)-6-phenyltellura-4H-pyran-4-one

Refernces

• 1、 Du, Xiaochen,Yu, Jiafeng,Gong, Jing,Zaman, Manzoor,Pereshivko, Olga P.,Peshkov, Vsevolod A.. "Gold-Catalyzed Post-Ugi Cascade Transformation for the Synthesis of 2-Pyridones". . p. 2502 - 2507. Retrieved 2019.
• 2、 Jing, Peng,Wu, Boyuan,Han, Zongsu,Shi, Wei,Cheng, Peng. "An efficient Ag/MIL-100(Fe) catalyst for photothermal conversion of CO2 at ambient temperature". . p. 3505 - 3508. Retrieved 2021.
• 3、 Shi, Jun-Bin,Bu, Qingqing,Liu, Bin-Yuan,Dai, Bin,Liu, Ning. "Organocatalytic Strategy for the Fixation of CO2via Carboxylation of Terminal Alkynes". . p. 1850 - 1860. Retrieved 2021/01/14.
• 4、 Bu, Ran,Zhang, Lin,Gao, Lu-Lu,Sun, Weng-Jie,Yang, Shuai-Liang,Gao, En-Qing. "Copper(I)-modified covalent organic framework for CO2 insertion to terminal alkynes". . . Retrieved 2020/12/21.