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

Base Information

• Chemical Name: Methyl 5-(3-aminophenyl)furan-2-carboxylate
• CAS No.: 54023-06-2
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.224
• Hs Code.: 2932190090
• European Community (EC) Number: 624-109-3
• DSSTox Substance ID: DTXSID70428090
• Mol file: 54023-06-2.mol

Synonyms:54023-06-2;Methyl 5-(3-aminophenyl)furan-2-carboxylate;5-(3-Aminophenyl)furan-2-carboxylic acid methyl ester;Methyl 5-(3-aminophenyl)-2-furoate;MFCD06739568;SCHEMBL1143419;2-Furancarboxylic acid, 5-(3-aminophenyl)-, methyl ester;DTXSID70428090;STK691792;AKOS005255327;SB61589;AS-37961;CS-0313175;FT-0640212;A829914;Methyl 5-(3-aminophenyl)furan-2-carboxylate, 97%

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

Chemical Property:

• Melting Point: 102-106 °C(lit.)
• Boiling Point: 411.2 °C at 760 mmHg
• Flash Point: 202.5 °C
• PSA: 65.46000
• Density: 1.222 g/cm³
• LogP: 2.89660
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 217.07389321
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

99% ^*data from raw suppliers

5-(3-Aminophenyl)furan-2-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Useful:

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

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

There total 7 articles about Methyl 5-(3-aminophenyl)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: 100.0%

5-(3-nitrophenyl)-furan-2-carboxylic acid methyl ester (41019-37-8) → 5-(3-amino-phenyl)-furan-2-carboxylic acid methyl ester (54023-06-2)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethyl acetate; for 3 - 4h; under 1034.32 - 1551.49 Torr; Product distribution / selectivity;

Reference yield: 71.0%

methyl 5-bromo-2-furoate (2527-99-3) + 3-Aminophenylboronic acid (30418-59-8,280563-63-5) → 5-(3-amino-phenyl)-furan-2-carboxylic acid methyl ester (54023-06-2)

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:

methyl 5-bromo-2-furoate (2527-99-3) → 5-(3-amino-phenyl)-furan-2-carboxylic acid methyl ester (54023-06-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / Pd(PPh₃)4; aq. Na₂CO₃ / toluene; methanol / 6 h / Heating

2: 51 percent / H₂ / Pd/C / methanol / 2 h / 20 °C / 2280 Torr

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; sodium carbonate; palladium on activated charcoal; In methanol; toluene; 1: Suzuki reaction;

DOI:10.1021/jm0492305

upstream raw materials:

5-(3-nitrophenyl)-furan-2-carboxylic acid methyl ester

5-(3-nitro-phenyl)-furan-2-carboxylic acid

methyl 5-bromo-2-furoate

m-nitrobenzene boronic acid

Downstream raw materials:

5-(3-(2-(5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl)-acetylamino)-phenyl)-furan-2-carboxylic acid

C₃₄H₃₈N₄O₆