Methyl 5-(3-hydroxyphenyl)furan-2-carboxylate

Base Information

• Chemical Name: Methyl 5-(3-hydroxyphenyl)furan-2-carboxylate
• CAS No.: 834884-73-0
• Molecular Formula: C12H10 O4
• Molecular Weight: 218.209
• DSSTox Substance ID: DTXSID20584599
• Wikidata: Q82476280
• Mol file: 834884-73-0.mol

Synonyms:Methyl 5-(3-hydroxyphenyl)furan-2-carboxylate;834884-73-0;5-(3-Hydroxyphenyl)furan-2-carboxylic acid methyl ester;METHYL 5-(3-HYDROXYPHENYL)FURAN-2-CARBO&;SCHEMBL1317340;DTXSID20584599;ZUIHUWQLICIWDI-UHFFFAOYSA-N;MFCD06797402;Methyl 5-(3-hydroxyphenyl)furan-2-carboxylate, 97%

Chemical Property of Methyl 5-(3-hydroxyphenyl)furan-2-carboxylate

Chemical Property:

• Vapor Pressure: 5.09E-07mmHg at 25°C
• Melting Point: 143-147 °C(lit.)
• Refractive Index: 1.567
• Boiling Point: 401.5°C at 760 mmHg
• Flash Point: 196.6°C
• PSA: 59.67000
• Density: 1.255g/cm³
• LogP: 2.43880
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 218.05790880
• Heavy Atom Count: 16
• Complexity: 253

Purity/Quality:

99% ^*data from raw suppliers

Methyl 5-(3-hydroxyphenyl)furan-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(O1)C2=CC(=CC=C2)O

Technology Process of Methyl 5-(3-hydroxyphenyl)furan-2-carboxylate

There total 2 articles about Methyl 5-(3-hydroxyphenyl)furan-2-carboxylate 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: 68.0%

methyl 5-bromo-2-furoate (2527-99-3) + 3-hydroxyphenylboronic acid (87199-18-6) → methyl 5-(3-hydroxyphenyl)furan-2-carboxylate (834884-73-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; Inert atmosphere; Reflux;

DOI:10.1016/j.ejmech.2020.112669

Reference yield:

5-bromo-furan-2-carboxylic acid (585-70-6) → methyl 5-(3-hydroxyphenyl)furan-2-carboxylate (834884-73-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 24 h / Reflux

2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,4-dioxane / 90 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; sulfuric acid; sodium carbonate; In 1,4-dioxane; water; 2: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.0c00373

Reference yield: 94.0%

methyl 5-(3-hydroxyphenyl)furan-2-carboxylate (834884-73-0) → 5-(3-hydroxyphenyl)furan-2-carboxylic acid (1235473-69-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; ethanol; water; for 5h; Reflux;

DOI:10.1021/acs.jmedchem.0c00373

upstream raw materials:

methyl 5-bromo-2-furoate

3-hydroxyphenylboronic acid

5-bromo-furan-2-carboxylic acid

Downstream raw materials:

5-(3-hydroxyphenyl)furan-2-carboxylic acid

5-(3-hydroxyphenyl)-furan-2-carboxylic acid 2-hydroxyethylamide